4-Trifluoromethylbenzyl chloroformate → 4-(Trifluoromethyl)benzyl (1R,2R)-2-((S)-1-(4-cyanophenyl)piperidin-3-ylamino)cyclohexylcarbamate
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[NH:22][C:23](=[O:35])CC3C4C(=CC=CC=4)N(C)C=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].C(Cl)(=O)[O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=1>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[NH:22][C:23](=[O:35])[O:37][CH2:38][C:39]3[CH:40]=[CH:41][C:42]([C:45]([F:46])([F:47])[F:48])=[CH:43][CH:44]=3)[CH2:10]2)=[CH:7][CH:8]=1)#[N:2]Participants
3
Procedure
4-(Trifluoromethyl)benzyl (1R,2R)-2-((S)-1-(4-cyanophenyl)piperidin-3-ylamino)cyclohexylcarbamate was synthesized using 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (from intermediate D, Example 10) (52 mg, 0.17 mmol) and 4-(trifluoromethyl)benzyl carbonochloridate (71.3 mg, 0.21 mmol) according to General Procedure H to give 27.4 mg (32.2%) of white solid. Anal. Calcd. for C22H31F3N4O2 m/z 500.2, found: 501.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.60 (d, J=8.1 Hz, 2H), 7.48 (m, 4H), 6.98 (d, J=9 Hz, 2H), 5.08 (s, 2H), 3.66 (m, 4H), 3.58 (m, 1H), 3.0 (m, 1H), 2.75 (m, 2H), 2.5 (m, 1H), 2.1 (d, 1H), 2.04 (s, 1H), 1.93 (s, 2H), 1.8 (m, 3H), 1.76 (s, 3H), 1.6 (m, 1H), 1.34 (m, 5H).
Sources & evidence
- ORD record
- ord-df9cadfc796f43fc996c8fb07cfca8bc
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710049B2
Reaction notes
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