HCID 71226691, compound → HCID 86690223, compound

HRID 2370005Notes

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][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH3:46])=[CH:40][CH:39]=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:47])[O:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH3:46])=[CH:40][CH:39]=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

Reactant 2

HCID 71226691HCID 71226691, compound2×

HCID 81647071HCID 81647071, compound

Product 1

HCID 86690223HCID 86690223, compound

Procedure

4-Ethoxyphenyl (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) (41 mg, 0.14 mmol) and 4-ethoxyphenyl carbonochloridate (22.6 mg, 0.14 mmol) according to General Procedure H to give 50 mg (78.3%) of white solid. Anal. Calcd. for C27H35N5O2 m/z 461.3, found: 462.4 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.28 (s, 1H), 7.41 (d, J=9 Hz, 2H), 7.28 (q, J=3.0 Hz, 2H), 6.92 (d, J=9 Hz, 2H), 6.8 (d, J=9 Hz, 2H), 5.97 (d, J=7.8 Hz, 1H), 3.95 (q, J=7.0 Hz, 2H), 3.88 (d, J=11.4 Hz, 1H), 3.77 (d, J=13 Hz, 1H), 3.25 (m, 1H), 2.78 (m, 1H), 2.58 (m, 1H), 2.39 (m, 2H), 1.88 (m, 3H), 1.68 (m, 1H), 1.61 (m, 3H), 1.47 (m, 1H), 1.30 (t, J=7.0 Hz, 3H), 1.2 (m, 4H), 1.11 (m, 1H).

Sources & evidence

ORD record: ord-8fbc29d87fd441d084c3fe5eacc70216
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710049B2

Reaction notes

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