2-Fluoro-5-(trifluoromethyl)pyridine → 1-Phenyl-3-((1R,2R)-2-((S)-1-(5-(trifluoromethyl)pyridin-2-yl)piperidin-3-ylamino)cyclohexyl)urea
Reaction equation
[C:1]1([NH:7][C:8]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[NH:17][CH:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=1>>[C:1]1([NH:7][C:8]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[NH:17][C@H:18]2[CH2:23][CH2:22][CH2:21][N:20]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=3)[CH2:19]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
3
Procedure
1-Phenyl-3-((1R,2R)-2-((S)-1-(5-(trifluoromethyl)pyridin-2-yl)piperidin-3-ylamino)cyclohexyl)urea was synthesized using 1-phenyl-3-((1R,2R)-2-(piperidin-3-ylamino)cyclohexyl)urea (from intermediate C, Example 1) (100 mg, 0.32 mmol) and 2-fluoro-5-(trifluoromethyl)pyridine (57.4 mg, 0.35 mmol) according to General Procedure A to give 15 mg (10.3%) of white solid. Anal. Calcd. for C24H30F3N5O m/z 461.2, found: 462.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 8.18 (m, 1H), 7.30 (m, 1H), 7.21 (m, 4H), 7.00 (m, 1H), 6.67 (d, J=8.9 Hz, 1H), 6.18 (d, J=5.4 Hz, 1H), 4.47 (m, 1H), 3.79 (m, 1H), 3.59 (m, 3H), 3.23 (m, 1H), 2.33 (m, 1H), 2.07 (m, 4H), 1.87 (m, 3H), 1.67 (d, J=7 Hz, 2H), 1.49 (m, 4H).
Sources & evidence
- ORD record
- ord-e4eee1ea1b7b4a70b86b24c355206c17
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710049B2
Reaction notes
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