Cyanogen Bromide → HCID 66940648, compound

HRID 1845064Notes

Reaction equation

HRID 1845064 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[C:10]1[CH:15]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=[C:12]([NH2:24])[C:11]=1[NH2:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC(C1C2N=C(N)[NH:36][C:35]=2C=CC=1)=O.BrC#N>CO>[CH2:1]([O:8][C:9]([C:10]1[C:11]2[N:25]=[C:35]([NH2:36])[NH:24][C:12]=2[CH:13]=[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=1)=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 24730367methyl 2-amino-1H-benzo[d]imidazole-4-carboxylateHCID 66940596HCID 66940596, compound

Product 1

HCID 66940648HCID 66940648, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5 g (7.2 mmol) of 2,3-diamino-5-benzyloxy-benzoic acid benzyl ester was subjected to a similar cyclization condition as illustrated in intermediate A by using 2.3 g (21.6 mmol) of BrCN in methanol to produce 2-amino-6-benzyloxy-1H-benzoimidazole-4-carboxylic acid benzyl ester. LCMS: 375 (M+1)+.

Sources & evidence

ORD record
ord-f2e84c52385842e8a14cd2af94b97fde
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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