4-Methylmorpholine → Ethyl 2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl](methyl)amino}piperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH3:19])[CH2:14][CH2:13]2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:20][C:21]1[N:22]=[C:23]([C:28]([OH:30])=O)[NH:24][C:25]=1[CH2:26][CH3:27].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>>[Cl:20][C:21]1[N:22]=[C:23]([C:28]([N:18]([CH3:19])[CH:15]2[CH2:16][CH2:17][N:12]([C:4]3[S:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([CH3:1])[N:3]=3)[CH2:13][CH2:14]2)=[O:30])[NH:24][C:25]=1[CH2:26][CH3:27]Participants
6
Reactant 5
Product 1
Procedure
The same operation as in Example (217c) was performed using ethyl 4-methyl-2-[4-(methylamino)piperidin-1-yl]-1,3-thiazole-5-carboxylate obtained in Example (240b) (254 mg, 0.90 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (156 mg, 0.90 mmol), WSC hydrochloride (515 mg, 2.69 mmol), 1-hydroxybenzotriazole (121 mg, 0.90 mmol) and N-methylmorpholine (0.20 mL, 1.79 mmol), to obtain 366 mg of the title compound as a white solid (93%).
Sources & evidence
- ORD record
- ord-ab3750081d1f41089ca66a7e0ef953b2
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536197B2
Reaction notes
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