2-Phenylethyl chloroformate → HCID 86690224, compound

HRID 2370011Notes

Reaction equation

HRID 2370011 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][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=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][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 159175902-Phenylethyl chloroformateHCID 71226691HCID 71226691, compound2×

Product 1

HCID 86690224HCID 86690224, compound

Procedure

Phenethyl(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 phenethyl carbonochloridate (52.9 mg, 0.18 mmol) according to General Procedure H to give 60 mg (80.4%) of pale yellow solid. Anal. Calcd. for C27H34N4O2 m/z 446.3, found: 447.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.54 (d, J=9 Hz, 2H), 7.24 (m, 5H), 6.98 (d, J=7 Hz, 3H), 4.13 (t, J=6.8 Hz, 2H), 3.89 (d, J=12.6 Hz, 1H), 3.76 (d, J=12.5 Hz, 1H), 3.05 (bs, 1H), 2.82 (m, 3H), 1.90 (m, 1H), 1.80 (m, 2H), 1.68 (m, 1H), 1.61 (m, 2H), 1.46 (m, 1H), 1.18-1.2 (m, 4H), 1.01 (m, 1H).

Sources & evidence

ORD record
ord-81bcfaad8b7647128657605b0a233a1b
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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