2-Methylcyclohexylamine hydrochloride, (1S,2S)- → 1-((1S,2S)-2-Methyl-cyclohexyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid

HRID 1750236Notes

Reaction equation

HRID 1750236 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]([OH:19])=[O:18])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:20][C:21]1[S:22][CH:23]=[CH:24][CH:25]=1.COC(=O)C1C=CC(N[C@H]2CCCC[C@@H]2C)=C(N)C=1.Cl.C[C@H]1CCCC[C@@H]1N>>[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]([OH:19])=[O:18])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:20][C:21]1[S:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 127142522-Methylcyclohexylamine hydrochloride, (1S,2S)-HCID 867144361-((1R,2R)-2-Methyl-cyclohexyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acidHCID 867144443-Amino-4-((1S,2S)-2-methyl-cyclohexylamino)-benzoic acid methyl ester

Product 1

HCID 867144431-((1S,2S)-2-Methyl-cyclohexyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid

Procedure

1-((1S,2S)-2-Methyl-cyclohexyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid was prepared in analogy to the synthesis of 1-((1R,2R)-2-Methyl-cyclohexyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid via 3-Amino-4-((1S,2S)-2-methyl-cyclohexylamino)-benzoic acid methyl ester and starting from (1S,2S)-2-Methyl-cyclohexylamine-hydrochloride.

Sources & evidence

ORD record
ord-35e0531eede94801bf04a3d3d0b7656a
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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