Diisopropylethylamine → Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-isopropoxypiperidin-1-yl)-4-(2-methoxyethylcarbamoyl)-1,3-thiazole-5-carboxylate

HRID 43742Notes

Reaction equation

HRID 43742 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][NH:16][CH2:15][C@H:14]2[O:19][CH:20]([CH3:22])[CH3:21])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9].C(N(C(C)C)CC)(C)C.Cl[C:33]1[S:34][C:35]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[C:36]([C:38](=[O:44])[NH:39][CH2:40][CH2:41][O:42][CH3:43])[N:37]=1>>[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][N:16]([C:33]3[S:34][C:35]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[C:36]([C:38](=[O:44])[NH:39][CH2:40][CH2:41][O:42][CH3:43])[N:37]=3)[CH2:15][C@H:14]2[O:19][CH:20]([CH3:21])[CH3:22])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 67073660Ethyl 2-chloro-4-[(2-methoxyethyl)carbamoyl]-1,3-thiazole-5-carboxylateHCID 86648687HCID 86648687, compound

Product 1

HCID 86648690Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-isopropoxypiperidin-1-yl)-4-(2-methoxyethylcarbamoyl)-1,3-thiazole-5-carboxylateYield 74%

Procedure

The same operation as in Example (1h) was performed using cis(±)-4-chloro-N-(3-isopropoxypiperidin-4-yl)-5-ethyl-1H-imidazole-2-carboxamide hydrochloride obtained in Example (148a) (0.150 g, 0.427 mmol), diisopropylethylamine (0.186 mL, 1.07 mmol) and ethyl 2-chloro-4-[(2-methoxyethyl)carbamoyl]-1,3-thiazole-5-carboxylate obtained in Example (149a) (0.167 g, 0.572 mmol), to obtain 0.180g of the title compound as a yellow solid (74%).

Sources & evidence

ORD record
ord-8d4d6760f7484771a7c40346978ff1f9
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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