Sodium Hydroxide → 2-tert-Butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1H-benzimidazole-4-carbonitrile

HRID 17556Notes

Reaction equation

HRID 17556 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([N:17]2[CH2:21][CH2:20][C@H:19]([N:22]([CH3:24])[CH3:23])[CH2:18]2)[C:3]=1[NH:25][C:26](=O)[C:27]([CH3:30])([CH3:29])[CH3:28].[OH-].[Na+]>C(O)(=O)C>[C:27]([C:26]1[NH:25][C:3]2[C:4]([N:17]3[CH2:21][CH2:20][C@H:19]([N:22]([CH3:24])[CH3:23])[CH2:18]3)=[C:5]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]([CH3:10])=[C:7]([C:8]#[N:9])[C:2]=2[N:1]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86630877N-[4-Amino-5-cyano-2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-methylbiphenyl-3-yl]-2,2-dimethylpropionamide

Product 1

HCID 529469142-tert-Butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1H-benzimidazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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).

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-44cfe75dbc2e4b838f77c05a72d46977
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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