Acetic Acid → HCID 178433639, compound

HRID 2271110Notes

Reaction equation

HRID 2271110 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:10]([C:15](=[O:25])[N:16]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[N:17]=3)=[CH:11][NH:12][C:13]=2[CH3:14])[CH:5]=[CH:6][CH:7]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]=O)[CH:27]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([N:16]2[C:15](=[O:25])[C:10]3=[CH:11][NH:12][C:13]([CH3:14])=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][CH2:32][C:28]5[CH:27]=[N:26][CH:31]=[CH:30][CH:29]=5)[CH:3]=4)[C:9]3=[N:17]2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 103713-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178433638HCID 178433638, compound

Product 1

HCID 178433639HCID 178433639, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 7-(3-aminophenyl)-2-(4-chlorophenyl)-2,5-dihydro-6-methylpyrazolo[4,3-c]pyridin-3-one (0.100 g, 0.285 mmol), 3-pyridinecarboxaldehyde (32.3 ml, 0.342 mmol), and acetic acid (65.5 ml, 1.14 mmol) in anhydrous methanol (4 ml) under nitrogen was added sodium cyanoborohydride (21.5 mg, 0.342 mmol) and the mixture was stirred for 3 h. The mixture was quenched with saturated aqueous K2CO3 (0.5 ml) and the solvent was removed in vacuo. The residue was purified by flash chromatography (silica gel, 5-10% MeOH/CH2Cl2) to give 0.1162 g (93%) of the title compound as a yellow solid; mp 284-287° C. (CH2Cl2-MeOH-EtOAc); 1H NMR (360 MHz, DMSO-d6) δ2.13 (3H, s), 4.34 (2H, d, J 6.1 Hz), 6.39 (1H, t, J 6.1 Hz), 6.64-6.68 (3H, m), 7.17 (1H, t, J 7.7 Hz), 7.35 (1H, dd, J 7.9, J′4.9 Hz), 7.42 (2H, d, J9.0 Hz), 7.77 (1H, dt), 8.11 (2H, d, J 9.0 Hz), 8.44 (1H, m), 8.51 (1H, s), 8.61 (1H, s), 12.34 (1H, br s); MS (ES+) m/z 442/444[MH]+, 221/222[(M2H)/2]+. Anal. found: C, 67.08; H, 4.50; N, 15.54. C25H20ClN5O.0.3H2O requires: C, 67.13; H, 4.64; N, 15.66%.

Workup

  1. customThe mixture was quenched with saturated aqueous K2CO3 (0.5 ml)
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by flash chromatography (silica gel, 5-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-cb5571a881e745fdac4e690351d7ed24
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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