N-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-2-(1-methyl-1H-indol-3-yl)acetamide → 4-Ethoxybenzyl (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(=O)CC3C4C(=CC=CC=4)N(C)C=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[C:36](Cl)(=[O:48])[O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH3:47])=[CH:41][CH:40]=1>>[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:36](=[O:48])[O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH3:47])=[CH:41][CH:40]=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]Participants
Procedure
4-Ethoxybenzyl (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) (50 mg, 0.17 mmol) and 4-ethoxybenzyl carbonochloridate (58.5 mg, 0.18 mmol) according to General Procedure H to give 65 mg (81%) of pale yellow solid. Anal. Calcd. for C28H36N4O3 m/z 476.3, found: 477.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.52 (d, J=8.9 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H), 1H), 7.04 (d, J=8.6 Hz, 1H), 6.95 (d, J=9 Hz, 2H), 6.84 (d, J=8.4 Hz, 2H), 4.92 (m, 2H), 3.98 (m, 2H), 3.86 (d, J=6.9 Hz, 1H), 3.75 (d, J=12.5 Hz, 1H), 3.07 (m, 1H), 2.76 (m, 1H), 2.35 (m, 2H), 1.89 (m, 1H), 1.78 (m, 2H), 1.64 (m, 3H), 1.44 (m, 1H), 1.30 (t. J=7 Hz, 3H), 1.17 (m, 4H), 1.02 (m, 1H).
Sources & evidence
- ORD record
- ord-ae77d36def0a4b7089174db365b7212d
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710049B2
Reaction notes
Loading…