Methyl 4-bromo-3-oxopentanoate → Methyl cis(+/-)-[2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methyl-1,3-thiazol-4-yl]acetate

HRID 43519Notes

Reaction equation

HRID 43519 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11]([C:13]2[NH:14][C:15]([CH2:19][CH3:20])=[C:16]([Cl:18])[N:17]=2)=[O:12])[C@H:6]([O:21][CH3:22])[CH2:5]1)(=[S:3])[NH2:2].Br[CH:24]([CH3:32])[C:25](=O)[CH2:26][C:27]([O:29][CH3:30])=[O:28]>>[Cl:18][C:16]1[N:17]=[C:13]([C:11]([NH:10][C@H:7]2[CH2:8][CH2:9][N:4]([C:1]3[S:3][C:24]([CH3:32])=[C:25]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[N:2]=3)[CH2:5][C@H:6]2[O:21][CH3:22])=[O:12])[NH:14][C:15]=1[CH2:19][CH3:20]

Participants

3

Reactant 2

HCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 86648527HCID 86648527, compound

Product 1

HCID 86648526Methyl cis(+/-)-[2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-5-methyl-1,3-thiazol-4-yl]acetateYield 84%

Procedure

The same operation as in Example (22b) was performed using cis(±)-N-(1-carbamothioyl-3-methoxypiperidin-4-yl)-4-chloro-5-ethyl-1H-imidazole-2-carboxamide (40 mg, 0.12 mmol) obtained in Example (65c) and methyl 4-bromo-3-oxopentanoate obtained in Example (65a) (45 mg, 0.22 mmol), to obtain 44.5 mg of the title compound (84%).

Sources & evidence

ORD record
ord-0aeb2f4b03ca4001b54a1f3e526d0ab5
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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