organic compounds
H-pyrazolo[3,4-b]pyridine-5-carbonitrile
of 3-methyl-1-phenyl-6-propylamino-1aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, eDepartment of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Assiut University, 71526 Assiut, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C17H17N5, the dihedral angle between the 1H-pyrazolo[3,4-b]pyridine ring system (r.m.s. deviation = 0.001 Å) and the attached phenyl group is 2.56 (6)°. The propylamino side chain has a contorted conformation [Car—N—C—C = −77.97 (16)° and N—C—C—C = −57.37 (17)°]. An intramolecular C—H⋯N interaction closes an S(6) ring. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R22(12) loops. Aromatic π–π stacking interactions [centroid–centroid distance = 3.5726 (8) Å] are also observed.
CCDC reference: 1423566
1. Related literature
For the chemistry of pyrazolo[3,4-b]pyridines, see: Häufel & Breitmaier (1974); El-emary (2007); Dodiya et al. (2013). For a similar structure, see: Wang & Zhu (2006).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: CrysAlis PRO (Agilent, 2014); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
CCDC reference: 1423566
10.1107/S2056989015017004/hb7504sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015017004/hb7504Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015017004/hb7504Isup3.cml
A mixture of 3-methyl-1-phenyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile (0.268 g, 1 mmol) and propyl amine (1.2 ml, 12 mmol) was heated to 323 K overnight with constant stirring. The reaction mixture was cooled to room temperature and taken up in dichloromethane, washed with 5% aq. NaHCO3, water and then with brine. The organic layer was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The crude product was recrystallized from aqueous ethanol to give the title compound as colourless prisms (0.2 g, 69% yield); Rf = 0.25 (hexane:ethyl acetate, 4:1).
The hydrogen atoms attached to carbon atoms were positioned geometrically and constrained to ride on their parent atoms, with carbon hydrogen bond distances of 0.93 - 0.97 Å. Uiso(H) values were set to a multiple of Ueq(C) with 1.5 for CH3 and 1.2 for CH and CH2, respectively. Reflection (-1 1 1) was affected by the beam stop and was omitted from the
The H atom of the NH group were found from a difference Fourier map and refinned freely.Data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).C17H17N5 | F(000) = 616 |
Mr = 291.36 | Dx = 1.277 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2809 reflections |
a = 5.1450 (2) Å | θ = 4.1–32.4° |
b = 15.1359 (7) Å | µ = 0.08 mm−1 |
c = 19.5828 (9) Å | T = 296 K |
β = 96.547 (4)° | Prism, colourless |
V = 1515.05 (12) Å3 | 0.44 × 0.22 × 0.18 mm |
Z = 4 |
Agilent Xcalibur Eos Gemini diffractometer | 5031 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3834 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 32.7°, θmin = 3.4° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −21→19 |
Tmin = 0.795, Tmax = 1.000 | l = −29→17 |
10807 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.5443P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5031 reflections | Δρmax = 0.39 e Å−3 |
205 parameters | Δρmin = −0.19 e Å−3 |
C17H17N5 | V = 1515.05 (12) Å3 |
Mr = 291.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.1450 (2) Å | µ = 0.08 mm−1 |
b = 15.1359 (7) Å | T = 296 K |
c = 19.5828 (9) Å | 0.44 × 0.22 × 0.18 mm |
β = 96.547 (4)° |
Agilent Xcalibur Eos Gemini diffractometer | 5031 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | 3834 reflections with I > 2σ(I) |
Tmin = 0.795, Tmax = 1.000 | Rint = 0.025 |
10807 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.39 e Å−3 |
5031 reflections | Δρmin = −0.19 e Å−3 |
205 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.1143 (2) | 0.39657 (8) | 0.17034 (6) | 0.0313 (3) | |
N2 | 0.1880 (2) | 0.35673 (7) | 0.23372 (5) | 0.0259 (3) | |
N3 | 0.0577 (2) | 0.36544 (7) | 0.34854 (5) | 0.0240 (3) | |
N4 | −0.1030 (2) | 0.38566 (8) | 0.45253 (6) | 0.0290 (3) | |
N5 | −0.6220 (3) | 0.54182 (8) | 0.43046 (6) | 0.0335 (3) | |
C1 | −0.0775 (3) | 0.45129 (9) | 0.17907 (7) | 0.0307 (4) | |
C2 | 0.0384 (2) | 0.38812 (8) | 0.28219 (6) | 0.0235 (3) | |
C3 | −0.1361 (3) | 0.44952 (8) | 0.24825 (7) | 0.0263 (3) | |
C4 | −0.3133 (3) | 0.49088 (8) | 0.28667 (7) | 0.0275 (3) | |
C5 | −0.3023 (2) | 0.46884 (8) | 0.35533 (7) | 0.0250 (3) | |
C6 | −0.1121 (2) | 0.40572 (8) | 0.38532 (6) | 0.0238 (3) | |
C7 | 0.0940 (3) | 0.32792 (9) | 0.48825 (7) | 0.0305 (4) | |
C8 | 0.0446 (3) | 0.22989 (10) | 0.47497 (8) | 0.0337 (4) | |
C9 | −0.2167 (4) | 0.19810 (12) | 0.49344 (10) | 0.0464 (5) | |
C10 | −0.4806 (3) | 0.50939 (8) | 0.39696 (7) | 0.0264 (3) | |
C11 | −0.2089 (4) | 0.50428 (11) | 0.12099 (8) | 0.0445 (5) | |
C12 | 0.3868 (2) | 0.29171 (8) | 0.23836 (7) | 0.0259 (3) | |
C13 | 0.5115 (3) | 0.27319 (9) | 0.18042 (8) | 0.0340 (4) | |
C14 | 0.7117 (3) | 0.21152 (10) | 0.18464 (9) | 0.0386 (4) | |
C15 | 0.7886 (3) | 0.16777 (9) | 0.24520 (9) | 0.0356 (4) | |
C16 | 0.6611 (3) | 0.18531 (10) | 0.30210 (8) | 0.0334 (4) | |
C17 | 0.4609 (3) | 0.24712 (9) | 0.29935 (7) | 0.0301 (4) | |
H4 | −0.43410 | 0.53170 | 0.26680 | 0.0330* | |
H4N | −0.206 (4) | 0.4127 (12) | 0.4777 (10) | 0.041 (5)* | |
H7A | 0.10150 | 0.33880 | 0.53730 | 0.0370* | |
H7B | 0.26340 | 0.34310 | 0.47430 | 0.0370* | |
H8A | 0.05460 | 0.21790 | 0.42670 | 0.0400* | |
H8B | 0.18220 | 0.19630 | 0.50130 | 0.0400* | |
H9A | −0.22310 | 0.20520 | 0.54190 | 0.0700* | |
H9B | −0.23880 | 0.13680 | 0.48150 | 0.0700* | |
H9C | −0.35420 | 0.23200 | 0.46870 | 0.0700* | |
H11A | −0.20430 | 0.56570 | 0.13330 | 0.0670* | |
H11B | −0.38750 | 0.48550 | 0.11120 | 0.0670* | |
H11C | −0.11980 | 0.49580 | 0.08100 | 0.0670* | |
H13 | 0.46060 | 0.30210 | 0.13910 | 0.0410* | |
H14 | 0.79530 | 0.19950 | 0.14600 | 0.0460* | |
H15 | 0.92450 | 0.12700 | 0.24780 | 0.0430* | |
H16 | 0.71030 | 0.15520 | 0.34290 | 0.0400* | |
H17 | 0.37710 | 0.25850 | 0.33810 | 0.0360* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0380 (6) | 0.0317 (6) | 0.0259 (5) | 0.0000 (5) | 0.0115 (5) | 0.0002 (4) |
N2 | 0.0282 (5) | 0.0285 (5) | 0.0227 (5) | −0.0009 (4) | 0.0100 (4) | −0.0025 (4) |
N3 | 0.0231 (5) | 0.0257 (5) | 0.0243 (5) | −0.0018 (4) | 0.0080 (4) | −0.0049 (4) |
N4 | 0.0303 (6) | 0.0340 (6) | 0.0244 (5) | 0.0061 (5) | 0.0104 (4) | −0.0027 (4) |
N5 | 0.0361 (6) | 0.0338 (6) | 0.0319 (6) | 0.0063 (5) | 0.0102 (5) | −0.0022 (5) |
C1 | 0.0382 (7) | 0.0286 (6) | 0.0268 (6) | −0.0021 (5) | 0.0102 (5) | 0.0009 (5) |
C2 | 0.0238 (5) | 0.0235 (5) | 0.0245 (6) | −0.0039 (4) | 0.0080 (4) | −0.0044 (4) |
C3 | 0.0312 (6) | 0.0229 (5) | 0.0260 (6) | −0.0025 (5) | 0.0089 (5) | −0.0014 (4) |
C4 | 0.0302 (6) | 0.0222 (5) | 0.0310 (6) | 0.0000 (5) | 0.0078 (5) | −0.0006 (5) |
C5 | 0.0249 (6) | 0.0221 (5) | 0.0293 (6) | −0.0007 (4) | 0.0085 (5) | −0.0039 (4) |
C6 | 0.0231 (5) | 0.0237 (5) | 0.0256 (6) | −0.0025 (4) | 0.0072 (4) | −0.0047 (4) |
C7 | 0.0281 (6) | 0.0374 (7) | 0.0259 (6) | 0.0016 (5) | 0.0030 (5) | −0.0027 (5) |
C8 | 0.0314 (7) | 0.0361 (7) | 0.0338 (7) | 0.0048 (6) | 0.0051 (5) | 0.0022 (6) |
C9 | 0.0460 (9) | 0.0489 (9) | 0.0465 (9) | −0.0075 (8) | 0.0150 (8) | 0.0028 (7) |
C10 | 0.0280 (6) | 0.0238 (5) | 0.0282 (6) | −0.0001 (5) | 0.0064 (5) | −0.0017 (5) |
C11 | 0.0614 (11) | 0.0417 (8) | 0.0317 (8) | 0.0091 (8) | 0.0110 (7) | 0.0074 (6) |
C12 | 0.0242 (6) | 0.0250 (6) | 0.0298 (6) | −0.0049 (5) | 0.0093 (5) | −0.0081 (5) |
C13 | 0.0412 (8) | 0.0314 (7) | 0.0326 (7) | 0.0002 (6) | 0.0179 (6) | −0.0048 (5) |
C14 | 0.0431 (8) | 0.0327 (7) | 0.0443 (8) | 0.0004 (6) | 0.0240 (7) | −0.0092 (6) |
C15 | 0.0299 (7) | 0.0293 (6) | 0.0492 (9) | 0.0002 (5) | 0.0110 (6) | −0.0110 (6) |
C16 | 0.0293 (7) | 0.0345 (7) | 0.0363 (7) | 0.0008 (5) | 0.0033 (5) | −0.0070 (6) |
C17 | 0.0263 (6) | 0.0359 (7) | 0.0292 (6) | −0.0001 (5) | 0.0083 (5) | −0.0079 (5) |
N1—N2 | 1.3930 (15) | C13—C14 | 1.386 (2) |
N1—C1 | 1.3143 (18) | C14—C15 | 1.376 (2) |
N2—C2 | 1.3732 (15) | C15—C16 | 1.382 (2) |
N2—C12 | 1.4148 (15) | C16—C17 | 1.388 (2) |
N3—C2 | 1.3366 (15) | C4—H4 | 0.9300 |
N3—C6 | 1.3406 (15) | C7—H7A | 0.9700 |
N4—C6 | 1.3463 (17) | C7—H7B | 0.9700 |
N4—C7 | 1.4556 (18) | C8—H8A | 0.9700 |
N5—C10 | 1.144 (2) | C8—H8B | 0.9700 |
C1—C3 | 1.421 (2) | C9—H9A | 0.9600 |
C1—C11 | 1.490 (2) | C9—H9B | 0.9600 |
C2—C3 | 1.4055 (18) | C9—H9C | 0.9600 |
C3—C4 | 1.395 (2) | C11—H11A | 0.9600 |
C4—C5 | 1.3802 (19) | C11—H11B | 0.9600 |
N4—H4N | 0.87 (2) | C11—H11C | 0.9600 |
C5—C10 | 1.4330 (19) | C13—H13 | 0.9300 |
C5—C6 | 1.4437 (16) | C14—H14 | 0.9300 |
C7—C8 | 1.523 (2) | C15—H15 | 0.9300 |
C8—C9 | 1.510 (3) | C16—H16 | 0.9300 |
C12—C17 | 1.3869 (19) | C17—H17 | 0.9300 |
C12—C13 | 1.394 (2) | ||
N2—N1—C1 | 106.80 (11) | C3—C4—H4 | 121.00 |
N1—N2—C2 | 110.43 (10) | C5—C4—H4 | 121.00 |
N1—N2—C12 | 118.66 (10) | N4—C7—H7A | 109.00 |
C2—N2—C12 | 130.87 (10) | N4—C7—H7B | 109.00 |
C2—N3—C6 | 115.13 (10) | C8—C7—H7A | 109.00 |
C6—N4—C7 | 123.36 (11) | C8—C7—H7B | 109.00 |
N1—C1—C3 | 110.86 (12) | H7A—C7—H7B | 108.00 |
N1—C1—C11 | 121.48 (13) | C7—C8—H8A | 109.00 |
C3—C1—C11 | 127.65 (14) | C7—C8—H8B | 109.00 |
N2—C2—N3 | 126.71 (11) | C9—C8—H8A | 109.00 |
N2—C2—C3 | 106.27 (11) | C9—C8—H8B | 109.00 |
N3—C2—C3 | 127.03 (11) | H8A—C8—H8B | 108.00 |
C1—C3—C2 | 105.65 (12) | C8—C9—H9A | 109.00 |
C1—C3—C4 | 136.75 (13) | C8—C9—H9B | 109.00 |
C2—C3—C4 | 117.60 (12) | C8—C9—H9C | 110.00 |
C3—C4—C5 | 117.40 (12) | H9A—C9—H9B | 109.00 |
C7—N4—H4N | 116.6 (13) | H9A—C9—H9C | 109.00 |
C6—N4—H4N | 119.6 (13) | H9B—C9—H9C | 109.00 |
C4—C5—C10 | 119.53 (11) | C1—C11—H11A | 109.00 |
C4—C5—C6 | 120.45 (11) | C1—C11—H11B | 109.00 |
C6—C5—C10 | 120.02 (12) | C1—C11—H11C | 109.00 |
N4—C6—C5 | 119.56 (11) | H11A—C11—H11B | 109.00 |
N3—C6—C5 | 122.37 (11) | H11A—C11—H11C | 110.00 |
N3—C6—N4 | 118.07 (11) | H11B—C11—H11C | 109.00 |
N4—C7—C8 | 114.17 (12) | C12—C13—H13 | 120.00 |
C7—C8—C9 | 113.92 (13) | C14—C13—H13 | 120.00 |
N5—C10—C5 | 179.66 (15) | C13—C14—H14 | 120.00 |
N2—C12—C13 | 118.95 (12) | C15—C14—H14 | 120.00 |
C13—C12—C17 | 119.75 (12) | C14—C15—H15 | 120.00 |
N2—C12—C17 | 121.30 (12) | C16—C15—H15 | 120.00 |
C12—C13—C14 | 119.66 (14) | C15—C16—H16 | 119.00 |
C13—C14—C15 | 120.95 (15) | C17—C16—H16 | 119.00 |
C14—C15—C16 | 119.09 (14) | C12—C17—H17 | 120.00 |
C15—C16—C17 | 121.11 (14) | C16—C17—H17 | 120.00 |
C12—C17—C16 | 119.43 (13) | ||
C1—N1—N2—C2 | −0.22 (14) | N1—C1—C3—C2 | 0.00 (16) |
C1—N1—N2—C12 | 177.73 (11) | N3—C2—C3—C1 | 179.11 (12) |
N2—N1—C1—C3 | 0.13 (15) | N2—C2—C3—C1 | −0.15 (14) |
N2—N1—C1—C11 | −178.72 (13) | N3—C2—C3—C4 | −1.3 (2) |
C2—N2—C12—C17 | 0.2 (2) | N2—C2—C3—C4 | 179.47 (12) |
N1—N2—C12—C17 | −177.28 (12) | C1—C3—C4—C5 | 179.97 (16) |
C12—N2—C2—N3 | 3.4 (2) | C2—C3—C4—C5 | 0.51 (19) |
N1—N2—C2—C3 | 0.23 (13) | C3—C4—C5—C6 | 0.41 (18) |
N1—N2—C2—N3 | −179.03 (11) | C3—C4—C5—C10 | −179.87 (12) |
C2—N2—C12—C13 | −179.14 (12) | C10—C5—C6—N3 | 179.49 (11) |
C12—N2—C2—C3 | −177.40 (12) | C4—C5—C6—N3 | −0.79 (18) |
N1—N2—C12—C13 | 3.40 (17) | C4—C5—C6—N4 | 179.43 (12) |
C2—N3—C6—C5 | 0.14 (17) | C10—C5—C6—N4 | −0.29 (17) |
C6—N3—C2—C3 | 0.91 (18) | N4—C7—C8—C9 | −57.37 (17) |
C2—N3—C6—N4 | 179.92 (11) | N2—C12—C13—C14 | 178.16 (12) |
C6—N3—C2—N2 | −180.00 (12) | C17—C12—C13—C14 | −1.2 (2) |
C7—N4—C6—C5 | −175.32 (11) | N2—C12—C17—C16 | −178.48 (12) |
C7—N4—C6—N3 | 4.89 (18) | C13—C12—C17—C16 | 0.8 (2) |
C6—N4—C7—C8 | −77.97 (16) | C12—C13—C14—C15 | 0.4 (2) |
C11—C1—C3—C2 | 178.77 (14) | C13—C14—C15—C16 | 0.8 (2) |
C11—C1—C3—C4 | −0.7 (3) | C14—C15—C16—C17 | −1.1 (2) |
N1—C1—C3—C4 | −179.50 (16) | C15—C16—C17—C12 | 0.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···N3 | 0.93 | 2.33 | 2.9823 (18) | 127 |
N4—H4N···N5i | 0.87 (2) | 2.20 (2) | 3.0326 (17) | 160.1 (18) |
Symmetry code: (i) −x−1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···N3 | 0.93 | 2.33 | 2.9823 (18) | 127 |
N4—H4N···N5i | 0.87 (2) | 2.20 (2) | 3.0326 (17) | 160.1 (18) |
Symmetry code: (i) −x−1, −y+1, −z+1. |
Acknowledgements
JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer. HHMA is also gratful to Professor Talaat I. El-emary, Assiut University, for his advice on the synthetic method.
References
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Pyrazolo[3,4-b]pyridines (Häufel & Breitmaier, 1974; El-Emary et al., 2007; Dodiya et al., 2013) are attractive targets in organic synthesis and are being extensively investigated because of their wide range of biological activities. We are interested in the synthesis of 6-amino derivatives of 3-methyl-1-phenyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile for potential biological interest.
The molecular structure of the title compound is shown in Fig. 1. The 1H-pyrazolo[3,4-b]pyridine ring system (N1—N3/C1—C6) is essentially planar [r.m.s. deviation = 0.001 Å]. It forms a dihedral angle of 2.56 (6) ° with the attached phenyl ring (C12—C17). All bond lengths and bond angles in the title compound are comparable with those of a similar structure previously published (Wang & Zhu, 2006).
In the crystal, pairs of N—H···O hydrogen bonds connect the molecules to each other, forming centrosymmetric dimers with R22(12) motifs (Table 1, Fig. 2). π-π stacking interactions between the dimers [Cg1···Cg3(-1 + x, y, z) = 3.5726 (8) Å] between the centroids of the phenyl and pyrazole rings of the molecules] are also observed.