Triethylamine → N-(2-Methoxyethyl)-3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethoxy)phenyl]piperidine-1-carboxamide
Reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][NH:14][CH2:13][CH:12]([NH:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:11]2)=[CH:6][CH:5]=1.[N:27]([CH2:30][CH2:31][O:32][CH3:33])=[C:28]=[O:29].C(N(CC)CC)C>C1COCC1>[CH3:33][O:32][CH2:31][CH2:30][NH:27][C:28]([N:14]1[CH2:15][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:25])[F:26])=[CH:9][CH:8]=2)[CH2:11][CH:12]([NH:16][C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:24])[CH2:13]1)=[O:29]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
70 mg (0.19 mmol) of N-{5-[4-(trifluoromethoxy)phenyl]piperidin-3-yl}benzamide were initially charged in 2.5 ml of THF, and 19 mg (0.19 mmol) of 1-isocyanato-2-methoxyethane and 29 μl (0.21 mmol) of triethylamine were added. The mixture was stirred at RT overnight. The reaction mixture was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 32 mg (35% of theory)
Workup
- customThe reaction mixture was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)
Sources & evidence
- ORD record
- ord-bbc31656cf824512a2653d2695757c00
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987248B2
Reaction notes
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