4-Methylmorpholine → Ethyl 3-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}azetidin-1-yl)benzoate
Reaction equation
[NH2:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3]1.[Cl:17][C:18]1[N:19]=[C:20]([C:25](O)=[O:26])[NH:21][C:22]=1[CH2:23][CH3:24].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>>[Cl:17][C:18]1[N:19]=[C:20]([C:25]([NH:1][CH:2]2[CH2:3][N:4]([C:6]3[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=3)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5]2)=[O:26])[NH:21][C:22]=1[CH2:23][CH3:24]Participants
6
Reactant 5
Product 1
Procedure
The same operation as in Example (217c) was performed using ethyl 3-(3-aminoazetidin-1-yl)benzoate obtained in Example (223b) (114 mg, 0.52 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (90 mg, 0.52 mmol), WSC hydrochloride (298 mg, 1.55 mmol), 1-hydroxybenzotriazole (70 mg, 0.52 mmol) and N-methylmorpholine (0.11 mL, 1.04 mmol), to obtain 87 mg of the title compound as a gray white solid (45%).
Sources & evidence
- ORD record
- ord-c0745ce1f7234f8089a8c573619724c3
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536197B2
Reaction notes
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