Cyanogen Bromide → 2-amino-6-ethylsulfanyl-1H-benzoimidazole-4-carboxylic acid ethyl ester

HRID 1910265Notes

Reaction equation

HRID 1910265 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([S:11][CH2:12][CH3:13])[CH:8]=[C:7]([NH2:14])[C:6]=1[NH2:15])[CH3:2].COC(C1C2N=C(N)[NH:26][C:25]=2C=CC=1)=O.BrC#N>CO>[CH2:1]([O:3][C:4]([C:5]1[C:6]2[N:15]=[C:25]([NH2:26])[NH:14][C:7]=2[CH:8]=[C:9]([S:11][CH2:12][CH3:13])[CH:10]=1)=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 24730367methyl 2-amino-1H-benzo[d]imidazole-4-carboxylateHCID 669405052,3-Diamino-5-ethylsulfanyl-benzoic acid ethyl ester

Product 1

HCID 669408182-amino-6-ethylsulfanyl-1H-benzoimidazole-4-carboxylic acid ethyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.9 g (3.75 mmol) of 2,3-diamino-5-ethylsulfanyl-benzoic acid ethyl ester was subjected to a similar cyclization condition as illustrated in intermediate A by using 1.2 g (11.3 mmol) of BrCN in methanol to produce 0.9 g (3.4 mmol, 90%) of 2-amino-6-ethylsulfanyl-1H-benzoimidazole-4-carboxylic acid ethyl ester. LCMS: 266 (M+1)+.

Sources & evidence

ORD record
ord-98b63c2595a64d0485660d9d8419c7db
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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