Pyridine → HCID 22318550, compound

HRID 497437Notes

Reaction equation

HRID 497437 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:23]3[C:24](=[O:43])[N:25]([CH:28]4[CH2:33][CH2:32][N:31]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=5[CH2:40][NH:41][CH3:42])[CH2:30][CH2:29]4)[CH2:26][CH2:27][C:22]=3[C:21]([C:44]([NH2:46])=[O:45])=[N:20]2)=[CH:15][CH:14]=1>C(Cl)Cl>[C:1]([N:41]([CH2:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[N:31]1[CH2:32][CH2:33][CH:28]([N:25]2[CH2:26][CH2:27][C:22]3[C:21]([C:44]([NH2:46])=[O:45])=[N:20][N:19]([C:16]4[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:18][CH:17]=4)[C:23]=3[C:24]2=[O:43])[CH2:29][CH2:30]1)[CH3:42])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 22318549HCID 22318549, compound

Product 1

HCID 22318550HCID 22318550, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Part H (17 mg, 0.02 mmol), acetyl chloride (0.05 mL), and pyridine (0.05 mL) in anhydrous CH2Cl2 (1 mL) was stirred at room temperature for 2 h under N2. Two products (1:5) were detected by LC/MS (ESI+): 531.6 (M+H) and 513.6 (M+H) for the amide (I-1) and the nitrile (I-2), respectively. The mixture was then concentrated in vacuo, and the residue was purified by prep LC-MS (5-98% CH3CN/H2O in a 10-min run) to obtain the product I-1, 6-[1-(2-{[acetyl(methyl)amino]methyl}phenyl)-4-piperidinyl]-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide (1.6 mg, 10%). LC/MS (ESI+), 531.6 (M+H). And product I-2, N-(2-{4-[3-cyano-1-(4-methoxyphenyl)-7-oxo-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-c]pyridin-6-yl]-1-piperidinyl}benzyl)-N-methylacetamide (8 mg, 50%). LC/MS (ESI+), 513.6 (M+H).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue was purified by prep LC-MS (5-98% CH3CN/H2O in a 10-min run)

Sources & evidence

ORD record
ord-660435b889de48d4a40ee6dc982e581a
Source dataset
uspto-grants-2005_09
Patent number
US06949550B2

Reaction notes

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