4-Chloro-2-pyridinecarbonitrile → 1-((1R,2R)-2-((S)-1-(2-Cyanopyridin-4-yl)piperidin-3-ylamino)cyclohexyl)-3-phenylurea
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.Cl[C:25]1[CH:30]=[CH:29][N:28]=[C:27]([C:31]#[N:32])[CH:26]=1>>[C:31]([C:27]1[CH:26]=[C:25]([N:20]2[CH2:21][CH2:22][CH2:23][C@H:18]([NH:17][C@@H:12]3[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]3[NH:10][C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:9])[CH2:19]2)[CH:30]=[CH:29][N:28]=1)#[N:32]Participants
3
Procedure
1-((1R,2R)-2-((S)-1-(2-Cyanopyridin-4-yl)piperidin-3-ylamino)cyclohexyl)-3-phenylurea 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 4-chloropicolinonitrile (44 mg, 0.15 mmol) according to General Procedure A to give 29.3 mg (22.1%) of pale brown oil. Anal. Calcd. for C24H30N6O m/z 418.2, found: 419.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.89 (d, J=6.5 Hz, 1H), 7.35 (d, J=2.7 Hz, 1H), 7.25 (m, 4H), 7.04 (m, 2H), 4.08 (m, 1H), 3.72 (m, 2H), 3.60 (m, 1H), 3.51 (m, 1H), 3.25 (m, 2H), 2.31 (m, 1H), 2.15-2.05 (m, 4H), 1.98-1.88 (m, 3H), 1.63-1.42 (m, 5H).
Sources & evidence
- ORD record
- ord-c40f8d167ef24349a24b0a4bd9e6de1f
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710049B2
Reaction notes
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