Acetic Acid → HCID 178433645, compound

HRID 2271115Notes

Reaction equation

HRID 2271115 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH:32]=O.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:5]4[CH:6]=[CH:7][C:2]([NH:1][CH2:32][C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=5)=[CH:3][CH:4]=4)[C:9]3=[N:17]2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 142732-PyridinecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178433644HCID 178433644, compound

Product 1

HCID 178433645HCID 178433645, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 7-(4-aminophenyl)-2-(4-chlorophenyl)-2,5-dihydro-6-methylpyrazolo[4,3-c]pyridin-3-one (0.150 g, 0.43 mmol), 2-pyridinecarboxaldehyde (81 μl, 0.85 mmol) and acetic acid (18 μl, 0.31 mmol) in anhydrous MeOH (3 ml) under nitrogen was added sodium cyanoborohydride (0.02 g, 0.32 mmol) and the mixture was stirred for 24 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 0.076 g (39.7%) of the title compound as a yellow solid; 1H NMR (360 MHz, DMSO-d6) δ12.32 (1H, br s), 8.57 (1H, d, J 2.1 Hz), 8.47 (1H, s), 8.14 (2H, d, J 8.7 Hz), 7.77 (1H, t, J 7.5 Hz), 7.43 (3H, m), 7.25 (3H, m), 6.68 (2H, d, J 8.3 Hz), 6.56 (2H, t, J 2.5 Hz), 4.41 (2H, d, J 5.8 Hz), 2.26 (3H, s); MS (ES+) m/z 442/444 [MH]+, 221/222 [(M+2H)/2]+.

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-c4c670ee4a224347a3f9380b456eeecd
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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