(3-Chlorophenyl)methyl chloroformate → HCID 86690220, compound

HRID 2369998Notes

Reaction equation

HRID 2369998 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][CH:42]=[C:41]([Cl:45])[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:23](=[O:35])[O:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 13292923(3-Chlorophenyl)methyl chloroformateHCID 71226691HCID 71226691, compound2×

Product 1

HCID 86690220HCID 86690220, compound

Procedure

3-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 3-chlorobenzyl carbonochloridate (68 mg, 0.22 mmol) according to General Procedure H to give 20 mg (21.3%) of white solid. Anal. Calcd. for C26H31ClN4O2 m/z 466.2, found: 467.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.46 (d, J=8.8 Hz, 2H), 7.35 (m, 1H), 7.30 (m, 4H), 7.28 (m, 2H), 7.23 (m, 1H), 6.96 (d, J=3 Hz, 2H), 5.0 (m, 2H), 3.71 (m, 1H), 3.58 (m, 1H), 3.29 (m, 1H), 2.98 (m, 1H), 2.72 (m, 2H), 2.52 (m, 1H), 2.04 (m, 1H), 1.92 (m, 2H), 1.78 (m, 3H), 1.62 (m, 1H), 1.34 (m, 4H), 1.20 (m, 1H).

Sources & evidence

ORD record
ord-94553516de3749e582a716febdce7fea
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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