4-Methylmorpholine → Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl](methyl)amino}azetidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:15][CH:14]([NH:16][CH3:17])[CH2:13]2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:18][C:19]1[N:20]=[C:21]([C:26]([OH:28])=O)[NH:22][C:23]=1[CH2:24][CH3:25].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>>[Cl:18][C:19]1[N:20]=[C:21]([C:26]([N:16]([CH3:17])[CH:14]2[CH2:13][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)[CH2:15]2)=[O:28])[NH:22][C:23]=1[CH2:24][CH3:25]Participants
6
Reactant 5
Product 1
Procedure
The same operation as in Example (217c) was performed using ethyl 4-methyl-2-[3-(methylamino)azetidin-1-yl]-1,3-thiazole-5-carboxylate obtained in Example (226b) (114 mg, 0.45 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (78 mg, 0.45 mmol), WSC hydrochloride (256 mg, 1.34 mmol), 1-hydroxybenzotriazole (60 mg, 0.45 mmol) and N-methylmorpholine (0.10 mL, 0.89 mmol), to obtain 167 mg of the title compound as a white solid (91%).
Sources & evidence
- ORD record
- ord-0a3c9124fd1f43d98269fb96e2ca88da
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536197B2
Reaction notes
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