Cyanogen Bromide → HCID 66940226, compound

HRID 1845059Notes

Reaction equation

HRID 1845059 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([O: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]([O: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 669407232,3-Diamino-5-ethoxy-benzoic acid ethyl ester

Product 1

HCID 66940226HCID 66940226, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.0 g (17.9 mmol) of 2,3-diamino-5-ethoxy-benzoic acid ethyl ester was subjected to a similar cyclization condition as illustrated in intermediate A by using 5.7 g (53.7 mmol) of BrCN in methanol to produce 2-amino-6-ethoxy-1H-benzoimidazole-4-carboxylic acid ethyl ester. LCMS: 250 (M+1)+.

Sources & evidence

ORD record
ord-d6809dce71be44fd9b7e6ff70c3ad49a
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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