p-Fluoronitrobenzene → 1-((1R,2R)-2-((S)-1-(4-Nitrophenyl)piperidin-3-ylamino)cyclohexyl)-3-phenylurea
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]1([NH:17][C:18]([NH:20][C@@H:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]2[NH:27][CH:28]2[CH2:33][CH2:32][CH2:31][NH:30][CH2:29]2)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:30]2[CH2:31][CH2:32][CH2:33][C@H:28]([NH:27][C@@H:22]3[CH2:23][CH2:24][CH2:25][CH2:26][C@H:21]3[NH:20][C:18]([NH:17][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:19])[CH2:29]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]Participants
Procedure
1-((1R,2R)-2-((S)-1-(4-Nitrophenyl)piperidin-3-ylamino)cyclohexyl)-3-phenylurea (15 mg) was synthesized in 13% yield using the procedures as described in General Procedure A using 1-fluoro-4-nitrobenzene (39.2 mg, 0.278 mmol) and 1-phenyl-3-((1R,2R)-2-(piperidin-3-ylamino)cyclohexyl)urea (80 mg, 0.253 mmol). Anal. Calcd. for C24H31N5O3 m/z 437.5, found: 438.4 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 9.12 (s, 1H), 7.66 (d, J=8.8 Hz, 2H), 7.37 (br. s., 1H), 7.31 (d, J=8.2 Hz, 2H), 7.15 (t, J=7.7 Hz, 2H), 6.98 (t, J=6.9 Hz, 1H), 6.59 (d, J=8.8 Hz, 2H), 3.68 (br. s., 3H), 3.43-3.34 (m, 1H), 3.26-3.17 (m, 2H), 2.95 (br. s., 1H), 2.32 (br. s., 1H), 2.20-2.11 (m, 1H), 2.05 (br. s., 2H), 1.96 (br. s., 2H), 1.82-1.75 (m, 1H), 1.65 (d, J=15.9 Hz, 2H), 1.46 (br. s., 1H), 1.19 (d, J=9.9 Hz, 2H); 13C NMR (126 MHz, CDCl3) δ ppm 158.96, 153.92, 138.94, 138.78, 128.79, 125.85, 122.92, 118.37, 113.48, 64.58, 53.54, 53.22, 49.48, 47.42, 45.94, 31.34, 29.50, 23.76, 21.69, 14.11, 8.63.
Sources & evidence
- ORD record
- ord-f1d1005a90df474f9eff03a67a2bc5e3
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710049B2
Reaction notes
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