[(S)-1-(4-Cyano-2-phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester → [(S)-1-(6-cyano-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester

HRID 242803Notes

Reaction equation

HRID 242803 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:13]=1[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]([C:10]1[N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]2[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:12]=2[N:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68157188[(S)-1-(4-Cyano-2-phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester

Product 1

HCID 68157544[(S)-1-(6-cyano-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [(S)-1-(4-cyano-2-phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester (750 mg, 1.97 mmol) in AcOH (3 mL) was stirred for 18 h at 80° C. After cooling to RT, volatiles were evaporated under reduced pressure affording [(S)-1-(6-cyano-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester (1.97 mmol) which was used without any further purification in the following step. LCMS: RT 3.55 min [M+H]+ 363.2.

Workup

  1. customvolatiles were evaporated under reduced pressure

Sources & evidence

ORD record
ord-88c97778fcb84cf9b49d96b152335604
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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