Reaction #45834

ord-44cfe75dbc2e4b838f77c05a72d46977

Reaction equation

Cc1c(C#N)c(N)c(NC(=O)C(C)(C)C)c(N2CC[C@H](N(C)C)C2)c1-c1ccccc1
N-[4-amino-5-cyano-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methylbiphenyl-3-yl]-2,2-dimethylpropionamide
[Na+].[OH-]
sodium hydroxide
→
Cc1c(-c2ccccc2)c(N2CC[C@H](N(C)C)C2)c2[nH]c(C(C)(C)C)nc2c1C#N
2-tert-Butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1H-benzimidazole-4-carbonitrile

Reactants

Cc1c(C#N)c(N)c(NC(=O)C(C)(C)C)c(N2CC[C@H](N(C)C)C2)c1-c1ccccc1
N-[4-amino-5-cyano-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methylbiphenyl-3-yl]-2,2-dimethylpropionamide
[Na+].[OH-]
sodium hydroxide

Reagents

None

Solvents

CC(=O)O
acetic acid

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureAfter cooling

Procedure

An acetic acid (5 ml) solution of N-[4-amino-5-cyano-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methylbiphenyl-3-yl]-2,2-dimethylpropionamide (I-270) (300 mg, 0.72 mmol) was heated at 80° C. for 2.5 hours. After cooling, the reaction solution was poured into aqueous sodium hydroxide solution (6.7 M, 15 ml).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07737166B2uspto-grants-2010_06