m-Tolyl isocyanate → HCID 71226857, compound

HRID 2370021Notes

Reaction equation

HRID 2370021 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].[N:36]([C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([CH3:45])[CH:40]=1)=C=O>>[C:1]([C:3]1[CH:4]=[CH:5][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]([NH:36][C:39]3[CH:40]=[C:41]([CH3:45])[CH:42]=[CH:43][CH:44]=3)=[O:35])[CH2:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 71226691N-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-2-(1-methyl-1H-indol-3-yl)acetamide2×

Product 1

HCID 71226857HCID 71226857, compound

Procedure

1-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-3-m-tolylurea 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 1-isocyanato-3-methylbenzene (22.3 mg, 0.17 mmol) according to General Procedure G to give 20 mg (27.7%) of a white solid. Anal. Calcd. for C26H33N5O m/z 431.3, found: 432.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.47 (s, 1H), 7.39 (d, J=8.9 Hz, 2H), 7.20 (s, 2H), 7.10 (t, J=8.1 Hz, 1H), 6.92 (d, J=8.9 Hz, 2H), 6.71 (d, J=7.4 Hz, 1H), 6.15 (d, J=7.6 Hz, 1H), 3.89 (d, J=11.1 Hz, 1H), 3.77 (d, J=13.2 Hz, 1H), 3.26 (d, J=8.9 Hz, 1H), 2.79 (m, 1H), 2.57 (m, 1H), 2.42 (m, 1H), 2.24 (s, 1H), 1.88 (m, 3H), 1.65 (m, 4H), 1.45 (m, 1H), 1.21 (m, 4H), 1.11 (m, 1H).

Sources & evidence

ORD record
ord-e5c343390ba84c3e8b6081ab563aaa14
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

Loading…