N-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-2-(1-methyl-1H-indol-3-yl)acetamide → 2-Chloro-4-methylbenzyl (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:47])[O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][C:40]=1[Cl:46]>>[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:47])[O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][C:40]=3[Cl:46])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]Participants
3
Procedure
2-Chloro-4-methylbenzyl (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 2-chloro-4-methylbenzyl carbonochloridate (59.3 mg, 0.18 mmol) according to General Procedure H to give 20 mg (24.8%) of white solid. Anal. Calcd. for C27H33ClN4O2 m/z 480.2, found: 481.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.43 (d, J=8.8 Hz, 2H), 7.27 (d, J=7.72 Hz, 2H), 7.19 (bs, 1H), 7.06 (m, 1H), 6.97 (m, 2H), 5.06 (m, 2H), 3.67 (m, 1H), 3.56 (m, 1H), 3.00 (m, 1H), 2.78 (m, 2H), 2.52 (m, 1H), 2.31 (s, 3H), 2.04 (m, 1H), 1.93 (m, 2H), 1.79 (m, 3H), 1.64 (m, 1H), 1.34 (m, 8H).
Sources & evidence
- ORD record
- ord-6f0781037cab4805b938c75b7dd71a1e
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710049B2
Reaction notes
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