HCID 13292931, compound → HCID 86690219, compound

HRID 2369997Notes

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]([CH3:45])[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]([CH3:45])[CH:40]=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

Reactant 2

HCID 13292931HCID 13292931, compound

HCID 71226691HCID 71226691, compound2×

Product 1

HCID 86690219HCID 86690219, compound

Procedure

3-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) (60 mg, 0.20 mmol) and 3-methylbenzyl carbonochloridate (63.5 mg, 0.22 mmol) according to General Procedure H to give 30 mg (33.4%) of white solid. Anal. Calcd. for C27H34N4O2 m/z 446.3, found: 447.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.45 (d, J=8.8 Hz, 2H), 7.19 (m, 1H), 7.12 (m, 2H), 6.97 (dd, J=8.8 Hz, J=2.8 Hz, 2H), 4.98 (m, 2H), 3.71 (m, 1H), 3.59 (m, 1H), 3.28 (m, 1H), 2.97 (m, 1H), 2.74 (m, 1H), 2.66 (m, 1H), 2.50 (m, 1H), 2.31 (s, 3H), 2.04 (m, 1H), 1.92 (m, 2H), 1.78 (m, 3H), 1.62 (m, 1H), 1.28 (m, 5H).

Sources & evidence

ORD record: ord-fe56323ace62430eadecbe7ac174362f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710049B2

Reaction notes

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