organic compounds
Methyl 2-(2-{[(benzyloxy)carbonyl]amino}propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate
aCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, People's Republic of China
*Correspondence e-mail: zhenhuashang@yahoo.com.cn
In the title compound, C17H19N3O6, the dihedral angle between the two aromatic rings is 45.9 (1)°. The is stabilized through intermolecular N—H⋯O hydrogen bonds and intramolecular O—H⋯O hydrogen bonds are also present.
Related literature
For related structures, see: Fun et al. (2009); Shang & Shang (2007). The title compound is an intermediate in the preparation of the antiretroviral drug raltegravir [systematic name N-(2-(4-(4-fluorobenzylcarbamoyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)-5-methyl-1,3,4-oxadiazole-2-carboxamide. For therapeutic details of raltegravir, see Steigbigel et al. (2008). For synthetic details, see: Culbertson (1979).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536811016278/wn2426sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811016278/wn2426Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811016278/wn2426Isup3.cml
The title compound was prepared by a published method (Culbertson, 1979). To a slurry of benzyl 1-amino-1-(hydroxyimino)-2-methylpropan-2-ylcarbamate (2.9 g) in methanol (12 ml) was added dimethyl acetylenedicarboxylate (1.77 g) slowly at room temperature. After 1.5 h, the mixture was added to xylene (20 ml). The reaction mixture was then heated to reflux for 2 h and cooled to 60 °C. Methyl tert-butyl ether (9 ml) was added slowly to build a seed bed. The batch was then cooled to 0 °C for 14 h, and then further cooled to -5 °C and allowed to stand for 1 h before filtration. The solid was washed with methyl tert-butyl ether (4 ml) and dried. 50 mg of the title compound was dissolved in 30 ml methanol and the solution was kept at room temperature for 10 d. Natural evaporation gave colorless single crystals of the title compound which were suitable for X-ray analysis.
All H atoms attached to C atoms were positioned geometrically and treated as riding with C—H = 0.95 Å (aromatic), 0.98 Å (methyl group) and 0.99 Å (methyene group). Uiso(H) = xUeq(C), where x = 1.5 for methyl H and 1.2 for all other carbon-bound H atoms. The positional parameters of the nitrogen-bound H and oxygen-bound H atoms were refined freely (N—H = 0.882 (15) and 0.938 (16) Å; O—H = 0.918 (17) Å).
Data collection: SMART (Bruker, 1997); cell
SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C17H19N3O6 | Dx = 1.379 Mg m−3 |
Mr = 361.35 | Melting point = 183–185 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.122 (2) Å | Cell parameters from 4990 reflections |
b = 16.300 (3) Å | θ = 2.5–27.9° |
c = 9.1766 (18) Å | µ = 0.11 mm−1 |
β = 106.29 (3)° | T = 113 K |
V = 1740.4 (6) Å3 | Plate, colorless |
Z = 4 | 0.24 × 0.20 × 0.16 mm |
F(000) = 760 |
Bruker SMART diffractometer | 4142 independent reflections |
Radiation source: rotating anode | 3386 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.035 |
ω scans | θmax = 27.9°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −15→15 |
Tmin = 0.975, Tmax = 0.983 | k = −21→18 |
15564 measured reflections | l = −11→12 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0539P)2 + 0.1964P] where P = (Fo2 + 2Fc2)/3 |
4142 reflections | (Δ/σ)max = 0.001 |
250 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C17H19N3O6 | V = 1740.4 (6) Å3 |
Mr = 361.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.122 (2) Å | µ = 0.11 mm−1 |
b = 16.300 (3) Å | T = 113 K |
c = 9.1766 (18) Å | 0.24 × 0.20 × 0.16 mm |
β = 106.29 (3)° |
Bruker SMART diffractometer | 4142 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 3386 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.983 | Rint = 0.035 |
15564 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.33 e Å−3 |
4142 reflections | Δρmin = −0.24 e Å−3 |
250 parameters |
Experimental. 1H-NMR (500 MHz, DMSO) 1.51(s, 6H), 3.82(s, 3H), 4.98(s, 2H), 7.35(bs, 5H), 7.45 (s, 1H), 10.24(s, 1H), 12.58(s, 1H) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.18567 (8) | 0.11941 (5) | 0.81459 (10) | 0.0159 (2) | |
N2 | 0.36822 (8) | 0.06461 (6) | 0.92786 (11) | 0.0179 (2) | |
N3 | 0.39582 (8) | 0.18366 (6) | 1.15086 (11) | 0.0170 (2) | |
O1 | 0.28432 (8) | −0.00917 (5) | 0.54614 (9) | 0.0247 (2) | |
O2 | 0.45987 (7) | −0.02265 (5) | 0.80609 (9) | 0.0282 (2) | |
O3 | 0.08230 (7) | 0.05655 (5) | 0.42611 (9) | 0.0234 (2) | |
O4 | 0.01176 (7) | 0.14406 (5) | 0.56692 (9) | 0.01951 (19) | |
O5 | 0.40819 (7) | 0.26902 (6) | 0.95868 (9) | 0.0279 (2) | |
O6 | 0.54363 (7) | 0.26725 (5) | 1.18631 (10) | 0.0285 (2) | |
C1 | 0.27523 (9) | 0.11186 (6) | 0.93025 (12) | 0.0148 (2) | |
C2 | 0.18776 (9) | 0.07855 (6) | 0.68378 (12) | 0.0160 (2) | |
C3 | 0.27744 (10) | 0.03116 (7) | 0.67123 (12) | 0.0176 (2) | |
C4 | 0.37656 (10) | 0.02098 (7) | 0.80389 (13) | 0.0196 (2) | |
C5 | 0.27947 (9) | 0.15246 (6) | 1.08134 (12) | 0.0157 (2) | |
C6 | 0.18968 (10) | 0.22037 (7) | 1.05981 (14) | 0.0215 (3) | |
H6A | 0.1929 | 0.2448 | 1.1585 | 0.032* | |
H6B | 0.1130 | 0.1973 | 1.0147 | 0.032* | |
H6C | 0.2055 | 0.2626 | 0.9924 | 0.032* | |
C7 | 0.25766 (11) | 0.08712 (7) | 1.18957 (13) | 0.0216 (3) | |
H7A | 0.3156 | 0.0437 | 1.2026 | 0.032* | |
H7B | 0.1810 | 0.0635 | 1.1472 | 0.032* | |
H7C | 0.2624 | 0.1122 | 1.2882 | 0.032* | |
C8 | 0.08872 (9) | 0.09093 (7) | 0.54685 (12) | 0.0171 (2) | |
C9 | −0.07754 (10) | 0.16603 (8) | 0.43090 (14) | 0.0259 (3) | |
H9A | −0.0423 | 0.1845 | 0.3526 | 0.039* | |
H9B | −0.1245 | 0.2103 | 0.4542 | 0.039* | |
H9C | −0.1262 | 0.1181 | 0.3938 | 0.039* | |
C10 | 0.44448 (10) | 0.24266 (7) | 1.08715 (13) | 0.0185 (2) | |
C11 | 0.60365 (11) | 0.33419 (8) | 1.13972 (14) | 0.0266 (3) | |
H11A | 0.5518 | 0.3818 | 1.1074 | 0.032* | |
H11B | 0.6333 | 0.3173 | 1.0541 | 0.032* | |
C12 | 0.70133 (10) | 0.35578 (7) | 1.27658 (13) | 0.0206 (3) | |
C13 | 0.68387 (11) | 0.36043 (8) | 1.41951 (14) | 0.0247 (3) | |
H13 | 0.6100 | 0.3491 | 1.4314 | 0.030* | |
C14 | 0.77345 (11) | 0.38150 (8) | 1.54519 (15) | 0.0284 (3) | |
H14 | 0.7609 | 0.3838 | 1.6427 | 0.034* | |
C15 | 0.88144 (11) | 0.39923 (8) | 1.52900 (16) | 0.0302 (3) | |
H15 | 0.9424 | 0.4144 | 1.6149 | 0.036* | |
C16 | 0.89961 (11) | 0.39465 (8) | 1.38730 (16) | 0.0282 (3) | |
H16 | 0.9733 | 0.4067 | 1.3755 | 0.034* | |
C17 | 0.80992 (10) | 0.37236 (7) | 1.26174 (15) | 0.0230 (3) | |
H17 | 0.8232 | 0.3685 | 1.1648 | 0.028* | |
H3 | 0.4221 (12) | 0.1800 (8) | 1.2505 (17) | 0.024 (3)* | |
H2 | 0.4269 (13) | 0.0577 (9) | 1.0186 (18) | 0.036 (4)* | |
H1 | 0.2178 (15) | 0.0049 (10) | 0.474 (2) | 0.045 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0170 (5) | 0.0159 (4) | 0.0139 (4) | −0.0015 (3) | 0.0029 (4) | −0.0008 (3) |
N2 | 0.0177 (5) | 0.0210 (5) | 0.0134 (4) | 0.0034 (4) | 0.0014 (4) | −0.0024 (4) |
N3 | 0.0182 (5) | 0.0189 (5) | 0.0116 (4) | −0.0021 (4) | 0.0004 (4) | −0.0005 (4) |
O1 | 0.0292 (5) | 0.0293 (5) | 0.0143 (4) | 0.0056 (4) | 0.0038 (4) | −0.0051 (3) |
O2 | 0.0265 (5) | 0.0372 (5) | 0.0188 (4) | 0.0140 (4) | 0.0029 (4) | −0.0049 (4) |
O3 | 0.0259 (5) | 0.0283 (4) | 0.0135 (4) | −0.0018 (3) | 0.0012 (3) | −0.0026 (3) |
O4 | 0.0173 (4) | 0.0220 (4) | 0.0158 (4) | 0.0007 (3) | −0.0010 (3) | 0.0012 (3) |
O5 | 0.0294 (5) | 0.0371 (5) | 0.0142 (4) | −0.0095 (4) | 0.0009 (3) | 0.0056 (4) |
O6 | 0.0273 (5) | 0.0334 (5) | 0.0189 (4) | −0.0152 (4) | −0.0031 (4) | 0.0055 (4) |
C1 | 0.0154 (5) | 0.0143 (5) | 0.0147 (5) | −0.0011 (4) | 0.0040 (4) | 0.0004 (4) |
C2 | 0.0180 (6) | 0.0156 (5) | 0.0129 (5) | −0.0018 (4) | 0.0019 (4) | 0.0005 (4) |
C3 | 0.0227 (6) | 0.0164 (5) | 0.0130 (5) | −0.0011 (4) | 0.0037 (4) | −0.0015 (4) |
C4 | 0.0220 (6) | 0.0202 (6) | 0.0158 (5) | 0.0029 (4) | 0.0040 (4) | −0.0011 (4) |
C5 | 0.0158 (5) | 0.0169 (5) | 0.0135 (5) | −0.0011 (4) | 0.0025 (4) | −0.0028 (4) |
C6 | 0.0209 (6) | 0.0212 (6) | 0.0209 (6) | 0.0033 (4) | 0.0034 (5) | −0.0051 (5) |
C7 | 0.0265 (6) | 0.0216 (6) | 0.0182 (6) | −0.0037 (4) | 0.0087 (5) | −0.0015 (4) |
C8 | 0.0183 (6) | 0.0171 (5) | 0.0149 (5) | −0.0043 (4) | 0.0031 (4) | 0.0009 (4) |
C9 | 0.0209 (6) | 0.0308 (7) | 0.0201 (6) | 0.0011 (5) | −0.0037 (5) | 0.0048 (5) |
C10 | 0.0197 (6) | 0.0209 (5) | 0.0139 (5) | −0.0017 (4) | 0.0030 (4) | −0.0018 (4) |
C11 | 0.0276 (7) | 0.0319 (7) | 0.0181 (6) | −0.0124 (5) | 0.0028 (5) | 0.0028 (5) |
C12 | 0.0208 (6) | 0.0190 (5) | 0.0204 (6) | −0.0025 (4) | 0.0034 (5) | 0.0002 (4) |
C13 | 0.0195 (6) | 0.0305 (6) | 0.0230 (6) | −0.0005 (5) | 0.0041 (5) | −0.0011 (5) |
C14 | 0.0306 (7) | 0.0309 (7) | 0.0206 (6) | 0.0027 (5) | 0.0020 (5) | −0.0040 (5) |
C15 | 0.0239 (6) | 0.0263 (6) | 0.0317 (7) | −0.0014 (5) | −0.0067 (5) | 0.0005 (5) |
C16 | 0.0172 (6) | 0.0249 (6) | 0.0390 (7) | −0.0007 (5) | 0.0019 (5) | 0.0080 (6) |
C17 | 0.0236 (6) | 0.0202 (6) | 0.0262 (6) | 0.0016 (4) | 0.0084 (5) | 0.0042 (5) |
N1—C1 | 1.2937 (14) | C6—H6A | 0.9800 |
N1—C2 | 1.3792 (14) | C6—H6B | 0.9800 |
N2—C4 | 1.3692 (15) | C6—H6C | 0.9800 |
N2—C1 | 1.3704 (14) | C7—H7A | 0.9800 |
N2—H2 | 0.938 (16) | C7—H7B | 0.9800 |
N3—C10 | 1.3446 (15) | C7—H7C | 0.9800 |
N3—C5 | 1.4663 (14) | C9—H9A | 0.9800 |
N3—H3 | 0.882 (15) | C9—H9B | 0.9800 |
O1—C3 | 1.3456 (14) | C9—H9C | 0.9800 |
O1—H1 | 0.918 (17) | C11—C12 | 1.5062 (16) |
O2—C4 | 1.2308 (14) | C11—H11A | 0.9900 |
O3—C8 | 1.2245 (14) | C11—H11B | 0.9900 |
O4—C8 | 1.3230 (14) | C12—C17 | 1.3874 (18) |
O4—C9 | 1.4491 (13) | C12—C13 | 1.3881 (18) |
O5—C10 | 1.2154 (14) | C13—C14 | 1.3872 (17) |
O6—C10 | 1.3489 (13) | C13—H13 | 0.9500 |
O6—C11 | 1.4413 (14) | C14—C15 | 1.389 (2) |
C1—C5 | 1.5242 (15) | C14—H14 | 0.9500 |
C2—C3 | 1.3646 (16) | C15—C16 | 1.380 (2) |
C2—C8 | 1.4881 (15) | C15—H15 | 0.9500 |
C3—C4 | 1.4602 (16) | C16—C17 | 1.3924 (18) |
C5—C6 | 1.5259 (15) | C16—H16 | 0.9500 |
C5—C7 | 1.5291 (16) | C17—H17 | 0.9500 |
C1—N1—C2 | 116.87 (10) | H7A—C7—H7C | 109.5 |
C4—N2—C1 | 123.91 (10) | H7B—C7—H7C | 109.5 |
C4—N2—H2 | 117.4 (9) | O3—C8—O4 | 123.86 (10) |
C1—N2—H2 | 118.4 (9) | O3—C8—C2 | 122.24 (11) |
C10—N3—C5 | 123.00 (9) | O4—C8—C2 | 113.87 (9) |
C10—N3—H3 | 115.1 (9) | O4—C9—H9A | 109.5 |
C5—N3—H3 | 116.8 (9) | O4—C9—H9B | 109.5 |
C3—O1—H1 | 104.1 (11) | H9A—C9—H9B | 109.5 |
C8—O4—C9 | 115.30 (9) | O4—C9—H9C | 109.5 |
C10—O6—C11 | 116.95 (9) | H9A—C9—H9C | 109.5 |
N1—C1—N2 | 123.03 (10) | H9B—C9—H9C | 109.5 |
N1—C1—C5 | 120.75 (10) | O5—C10—N3 | 126.23 (11) |
N2—C1—C5 | 116.14 (9) | O5—C10—O6 | 124.12 (11) |
C3—C2—N1 | 123.81 (10) | N3—C10—O6 | 109.62 (9) |
C3—C2—C8 | 118.60 (10) | O6—C11—C12 | 105.89 (9) |
N1—C2—C8 | 117.51 (10) | O6—C11—H11A | 110.6 |
O1—C3—C2 | 126.16 (10) | C12—C11—H11A | 110.6 |
O1—C3—C4 | 114.98 (10) | O6—C11—H11B | 110.6 |
C2—C3—C4 | 118.86 (10) | C12—C11—H11B | 110.6 |
O2—C4—N2 | 122.55 (10) | H11A—C11—H11B | 108.7 |
O2—C4—C3 | 123.97 (11) | C17—C12—C13 | 118.85 (11) |
N2—C4—C3 | 113.48 (10) | C17—C12—C11 | 120.61 (12) |
N3—C5—C1 | 109.22 (9) | C13—C12—C11 | 120.53 (11) |
N3—C5—C6 | 111.64 (9) | C14—C13—C12 | 120.51 (12) |
C1—C5—C6 | 110.88 (9) | C14—C13—H13 | 119.7 |
N3—C5—C7 | 106.23 (9) | C12—C13—H13 | 119.7 |
C1—C5—C7 | 108.70 (9) | C13—C14—C15 | 120.27 (13) |
C6—C5—C7 | 110.02 (10) | C13—C14—H14 | 119.9 |
C5—C6—H6A | 109.5 | C15—C14—H14 | 119.9 |
C5—C6—H6B | 109.5 | C16—C15—C14 | 119.59 (12) |
H6A—C6—H6B | 109.5 | C16—C15—H15 | 120.2 |
C5—C6—H6C | 109.5 | C14—C15—H15 | 120.2 |
H6A—C6—H6C | 109.5 | C15—C16—C17 | 119.98 (12) |
H6B—C6—H6C | 109.5 | C15—C16—H16 | 120.0 |
C5—C7—H7A | 109.5 | C17—C16—H16 | 120.0 |
C5—C7—H7B | 109.5 | C12—C17—C16 | 120.77 (13) |
H7A—C7—H7B | 109.5 | C12—C17—H17 | 119.6 |
C5—C7—H7C | 109.5 | C16—C17—H17 | 119.6 |
C2—N1—C1—N2 | −1.36 (16) | N1—C1—C5—C7 | 102.55 (12) |
C2—N1—C1—C5 | −178.04 (9) | N2—C1—C5—C7 | −74.35 (12) |
C4—N2—C1—N1 | 0.28 (18) | C9—O4—C8—O3 | −5.78 (16) |
C4—N2—C1—C5 | 177.10 (10) | C9—O4—C8—C2 | 171.97 (9) |
C1—N1—C2—C3 | 0.47 (16) | C3—C2—C8—O3 | 4.06 (17) |
C1—N1—C2—C8 | −176.14 (10) | N1—C2—C8—O3 | −179.15 (10) |
N1—C2—C3—O1 | −179.23 (10) | C3—C2—C8—O4 | −173.74 (10) |
C8—C2—C3—O1 | −2.66 (18) | N1—C2—C8—O4 | 3.06 (14) |
N1—C2—C3—C4 | 1.43 (17) | C5—N3—C10—O5 | −11.21 (19) |
C8—C2—C3—C4 | 178.00 (10) | C5—N3—C10—O6 | 170.86 (10) |
C1—N2—C4—O2 | −178.10 (11) | C11—O6—C10—O5 | 5.83 (18) |
C1—N2—C4—C3 | 1.58 (16) | C11—O6—C10—N3 | −176.18 (10) |
O1—C3—C4—O2 | −2.06 (18) | C10—O6—C11—C12 | 173.06 (10) |
C2—C3—C4—O2 | 177.35 (11) | O6—C11—C12—C17 | 137.37 (11) |
O1—C3—C4—N2 | 178.27 (10) | O6—C11—C12—C13 | −43.44 (15) |
C2—C3—C4—N2 | −2.32 (16) | C17—C12—C13—C14 | 0.16 (18) |
C10—N3—C5—C1 | 63.17 (13) | C11—C12—C13—C14 | −179.05 (11) |
C10—N3—C5—C6 | −59.82 (14) | C12—C13—C14—C15 | 0.83 (19) |
C10—N3—C5—C7 | −179.76 (10) | C13—C14—C15—C16 | −0.91 (19) |
N1—C1—C5—N3 | −141.95 (10) | C14—C15—C16—C17 | 0.00 (19) |
N2—C1—C5—N3 | 41.15 (12) | C13—C12—C17—C16 | −1.07 (17) |
N1—C1—C5—C6 | −18.51 (14) | C11—C12—C17—C16 | 178.14 (11) |
N2—C1—C5—C6 | 164.59 (10) | C15—C16—C17—C12 | 1.00 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O5i | 0.882 (15) | 2.133 (15) | 2.8911 (14) | 143.7 (12) |
N2—H2···O2ii | 0.938 (16) | 1.886 (16) | 2.8135 (16) | 169.3 (13) |
O1—H1···O3 | 0.918 (17) | 1.788 (17) | 2.6163 (14) | 148.7 (16) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C17H19N3O6 |
Mr | 361.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 113 |
a, b, c (Å) | 12.122 (2), 16.300 (3), 9.1766 (18) |
β (°) | 106.29 (3) |
V (Å3) | 1740.4 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.24 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.975, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15564, 4142, 3386 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.103, 1.09 |
No. of reflections | 4142 |
No. of parameters | 250 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.33, −0.24 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O5i | 0.882 (15) | 2.133 (15) | 2.8911 (14) | 143.7 (12) |
N2—H2···O2ii | 0.938 (16) | 1.886 (16) | 2.8135 (16) | 169.3 (13) |
O1—H1···O3 | 0.918 (17) | 1.788 (17) | 2.6163 (14) | 148.7 (16) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z+2. |
Acknowledgements
The authors thank the funds of Hebei Province Science and Technology Research and Development Projects (No. 08276409D) and Hebei University of Science and Technology.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Raltegravir (MK-0518, brand name Isentress), an antiretroviral drug produced by Merck & Co, is used to treat HIV infection (Steigbigel et al., 2008). It received FDA approval in October 2007, the first of a new class of HIV drugs, the integrase inhibitors, to receive such approval. The title compound is a key intermediate in the preparation of Raltegravir.
The pyrimidinone ring is planar, as it is in a related compound (Fun et al., 2009). This is in contrast with another related compound (Shang et al., 2007), where the heterocyclic ring is twisted. In the title compound the dihedral angle between the two aromatic rings is 45.9 (1)°. The crystal structure is stabilized through intermolecular N—H···O hydrogen bonds; intramolecular O—H···O hydrogen bonds are also present.