3-Chlorophenylacetic acid → 2-[6-Chloro-5-fluoro-2-(methoxy-phenyl-methyl)-benzoimidazol-1-yl]-N-cyclohexyl-3-(tetrahydro-thiopyran-4-yl)-propionamide

HRID 1170704Notes

Reaction equation

HRID 1170704 reaction equation
[CH2:1]([C:8]1[N:12]([CH:13]([CH:23]2[CH2:28][CH2:27][CH2:26]CC2)[C:14]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:15])[C:11]2[CH:29]=[C:30]([Cl:34])[C:31]([F:33])=[CH:32][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([CH:41]=[O:42])CCCCC1.[S:43]1CCC(CC=O)[CH2:45][CH2:44]1.ClC1C=C(CC(O)=O)C=CC=1.COC(C(O)=O)C1C=CC=CC=1>>[Cl:34][C:30]1[C:31]([F:33])=[CH:32][C:10]2[N:9]=[C:8]([CH:1]([O:42][CH3:41])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:12]([CH:13]([CH2:23][CH:28]3[CH2:27][CH2:26][S:43][CH2:44][CH2:45]3)[C:14]([NH:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:15])[C:11]=2[CH:29]=1

Participants

6

Reactant 5

HCID 158793-Chlorophenylacetic acidHCID 16275CyclohexanecarboxaldehydeHCID 107202Methoxyphenylacetic acidHCID 23532962(Tetrahydro-thiopyran-4-YL)-acetaldehydeHCID 673736232-(2-Benzyl-6-chloro-5-fluoro-benzoimidazol-1-yl)-2,N-dicyclohexyl-acetamide

Product 1

HCID 673705052-[6-Chloro-5-fluoro-2-(methoxy-phenyl-methyl)-benzoimidazol-1-yl]-N-cyclohexyl-3-(tetrahydro-thiopyran-4-yl)-propionamide

Procedure

The title compound was prepared in analogy to Example 1, replacing (2-amino-4,5-difluoro-phenyl)-carbamic acid tert-butyl ester with (2-amino-4-chloro-5-fluoro-phenyl)-carbamic acid tert-butyl ester (([CAS RN 579474-50-3]), Example 47), cyclohexanecarbaldehyde with tetrahydro-2H-thiopyran-4-acetaldehyde ([CAS RN 372159-78-9]) and (3-chloro-phenyl)-acetic acid with DL-α-methoxyphenylacetic acid ([CAS RN 7021-09-2]). MS (ISP): 544.3 [M+H]+.

Sources & evidence

ORD record
ord-3a81bb9da60c45c6a6c0f13a044c4c03
Source dataset
uspto-grants-2010_11
Patent number
US07825258B2

Reaction notes

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