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

HRID 1170716Notes

Reaction equation

HRID 1170716 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]C[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)C1C=CC=CC=1.[CH:35]1(C=O)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1.[S:43]1CCC(CC=O)[CH2:45][CH2:44]1.ClC1C=C(C[C:60](O)=[O:61])C=CC=1.C1(C(OC)C(O)=O)CCCCC1.C1([N+]#[C-])CCCCC1.C1([N+]#[C-])CCCC1>>[Cl:34][C:30]1[C:31]([F:33])=[CH:32][C:10]2[N:9]=[C:8]([CH:1]([CH:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)[O:61][CH3:60])[N:12]([CH:13]([CH2:23][CH:28]3[CH2:45][CH2:44][S:43][CH2:26][CH2:27]3)[C:14]([NH:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:18]3)=[O:15])[C:11]=2[CH:29]=1

Participants

8

Reactant 7

HCID 158793-Chlorophenylacetic acidHCID 16275CyclohexanecarboxaldehydeHCID 79129Cyclohexyl isocyanideHCID 2734784Cyclopentyl IsocyanideHCID 215051022-Cyclohexyl-2-methoxyacetic acidHCID 23532962(Tetrahydro-thiopyran-4-YL)-acetaldehydeHCID 673736232-(2-Benzyl-6-chloro-5-fluoro-benzoimidazol-1-yl)-2,N-dicyclohexyl-acetamide

Product 1

HCID 673733172-[6-Chloro-2-(cyclohexyl-methoxy-methyl)-5-fluoro-benzoimidazol-1-yl]-N-cyclopentyl-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]), (3-chloro-phenyl)-acetic acid with DL-cyclohexyl-methoxy-acetic acid ([CAS RN 15540-18-8]) and cyclohexyl isocyanide with cyclopentyl isocyanide ([CAS RN 68498-54-4]). MS (ISP): 536.3 [M+H]+.

Sources & evidence

ORD record
ord-f15489579be04efcbb3790ec151903bc
Source dataset
uspto-grants-2010_11
Patent number
US07825258B2

Reaction notes

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