Diisopropylethylamine → Ethyl cis(+/-)-6-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylpyrimidine-4-carboxylate

HRID 43770Notes

Reaction equation

HRID 43770 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][CH3:20])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9].Cl[C:22]1[N:27]=[C:26]([CH3:28])[N:25]=[C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:23]=1.C(N(C(C)C)CC)(C)C>>[Cl:2][C:3]1[N:4]=[C:5]([C:10]([NH:12][C@H:13]2[CH2:18][CH2:17][N:16]([C:22]3[N:27]=[C:26]([CH3:28])[N:25]=[C:24]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:23]=3)[CH2:15][C@H:14]2[O:19][CH3:20])=[O:11])[NH:6][C:7]=1[CH2:8][CH3:9]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 71464314Ethyl 6-chloro-2-methylpyrimidine-4-carboxylateHCID 86648695cis(+/-)-4-Chloro-5-ethyl-N-(3-methoxypiperidin-4-yl)-1H-imidazole-2-carboxamide hydrochloride

Product 1

HCID 86648718Ethyl cis(+/-)-6-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-2-methylpyrimidine-4-carboxylateYield 21.4%

Procedure

The same operation as in Example (158a) was performed using cis(±)-4-chloro-5-ethyl-N-(3-methoxypiperidin-4-yl)-1H-imidazole-2-carboxamide hydrochloride obtained in Example (159a) (94.7 mg, 0.29 mmol), ethyl 6-chloro-2-methylpyrimidine-4-carboxylate (56 mg, 0.28 mmol) (reference: Bioorganic and Medicinal Chemistry Letters; 14; 15; 2004; 3869-3874) and diisopropylethylamine (108 mg, 0.84 mmol), to obtain 27 mg of the title compound as a yellow brown oily substance (22%).

Sources & evidence

ORD record
ord-99342a84f49b430db5f8092a19e7414a
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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