Cyanogen Bromide → 2-Amino-6-methoxy-1H-benzimidazole-7-carboxylic acid

HRID 1845076Notes

Reaction equation

HRID 1845076 reaction equation
[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[C:3]=1[C:4]([OH:6])=[O:5].COC(C1C2N=C(N)[NH:23][C:22]=2C=CC=1)=O.BrC#N>CO>[NH2:23][C:22]1[NH:11][C:10]2[CH:9]=[CH:8][C:7]([O:12][CH3:13])=[C:3]([C:4]([OH:6])=[O:5])[C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11030440HCID 11030440, compoundHCID 24730367methyl 2-amino-1H-benzo[d]imidazole-4-carboxylate

Product 1

HCID 669404002-Amino-6-methoxy-1H-benzimidazole-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.8 g (4.4 mmol) of 2,3-diamino-6-methoxy-benzoic acid was subjected to a similar cyclization condition as illustrated in intermediate A by using 0.7 g (6.6 mmol) of BrCN in methanol to produce 2-amino-5-methoxy-1H-benzoimidazole-4-carboxylic acid. LCMS: 208 (M+1)+.

Sources & evidence

ORD record
ord-b2adacb1212044b68c3db01805235dfc
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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