(4-Chlorophenyl)methyl chloroformate → HCID 86690218, compound

HRID 2369996Notes

Reaction equation

HRID 2369996 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:46])[O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[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:46])[O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 13292914(4-Chlorophenyl)methyl chloroformateHCID 71226691HCID 71226691, compound2×

Product 1

HCID 86690218HCID 86690218, compound

Procedure

4-Chlorobenzyl (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) (60 mg, 0.20 mmol) and 4-chlorobenzyl carbonochloridate (68 mg, 0.22 mmol) according to General Procedure H to give 25 mg (26.6%) of white solid. Anal. Calcd. for C26H31ClN4O2 m/z 466.2, found: 467.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.48 (d, J=8.9 Hz, 2H), 7.30 (s, 4H), 6.98 (d, J=9 Hz, 2H), 4.99 (m, 2H), 3.70 (m, 1H), 3.57 (m, 1H), 3.29 (m, 1H), 2.98 (m, 1H), 2.75 (m, 1H), 2.68 (m, 1H), 2.50 (m, 1H), 2.04 (m, 1H), 1.91 (m, 2H), 1.77 (m, 3H), 1.64 (m, 1H), 1.32 (m, 5H), 1.21 (m, 1H).

Sources & evidence

ORD record
ord-f2c5d64e743f4e9ab093e104e8109021
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

Loading…