Methyl 4-amino-3-(trifluoromethyl)benzoate → 4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-3-trifluoromethyl-benzoic acid methyl ester

HRID 1161330Notes

Reaction equation

HRID 1161330 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:38])[CH:13]([N:20]2[C:24]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:23]=3[N:22]=[C:21]2[C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1)C.ClC1C=CC(C2N(C(C3CCCCC3)C(NC[C@H]3CC[C@H](C(O)=O)CC3)=O)C3C=CC(F)=CC=3N=2)=CC=1.COC(=O)C1C=CC(N)=C([C:87]([F:90])([F:89])[F:88])C=1>N1C=CC=CC=1>[CH3:1][O:3][C:4](=[O:39])[C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:38])[CH:13]([N:20]2[C:24]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:23]=3[N:22]=[C:21]2[C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)[CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:9]([C:87]([F:90])([F:89])[F:88])[CH:10]=1

Participants

5

Reactant 3

HCID 25067388Methyl 4-amino-3-(trifluoromethyl)benzoateHCID 686454934-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-benzoic acid ethyl esterHCID 178523387HCID 178523387, compound2×

Product 1

HCID 866320234-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-3-trifluoromethyl-benzoic acid methyl esterYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

This compound was synthesized in analogy to example 20, intermediate d, from [2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid (example 20, intermediate c), 4-amino-3-trifluoromethyl-benzoic acid methyl ester and using pyridine as a base to afford the title compound as a colorless solid (74%).

Sources & evidence

ORD record
ord-bfecd1a8ba8e42e79522be3515f9dbf4
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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