HCID 178430969, compound → HCID 178430523, compound
Reaction equation
[CH3:1][C:2]1[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[C:5]([C:11]([NH2:13])=O)=[CH:4][C:3]=1[N+:14]([O-])=O.CC1C2NC=NC=2C(C#N)=CC=1[N+]([O-])=O>>[NH2:14][C:3]1[CH:4]=[C:5]([C:11]#[N:13])[C:6]2[N:10]=[CH:9][NH:8][C:7]=2[C:2]=1[CH3:1]Participants
Procedure
As to General Reaction Scheme 3, intermediate (22) (produced via, inter alia, General Scheme 2) is nitrated by a nitrating agent to yield intermediate 7-Methyl-6-nitro-1H-benzimidazole-4-carboxylic acid (23). In turn, intermediate (23) may either be amidated/dehydrated by an amidating/dehydrating agent to yield intermediate 7-Methyl-6-nitro-1H-benzimidazole-4-carbonitrile (24), or amidated by an amidating agent to yield intermediate 7-Methyl-6-nitro-1H-benzimidazole-4-carboxamide (25). Intermediate (24) is reduced by a nitro group reducing agent to yield intermediate (10). In turn, intermediate (25) is reduced by a nitro group reducing agent to yield intermediate 6-Amino-7-methyl-1H-benzimidazole-4-carboxamide, hydrochloric acid salt (26), and thereafter dehydrated by an amide dehydrating agent to yield intermediate (10). See Examples 13 and 14.
Sources & evidence
- ORD record
- ord-a33801b3311d4d11bf91fcead776bb26
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07304084B2
Reaction notes
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