4-Methylphenyl isocyanate → HCID 86690225, compound

HRID 2370014Notes

Reaction equation

HRID 2370014 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][C:42]([CH3:45])=[CH:41][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:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=3)=[O:35])[CH2:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

3

Reactant 2

HCID 693254-Methylphenyl isocyanateHCID 71226691N-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-2-(1-methyl-1H-indol-3-yl)acetamide2×

Product 1

HCID 86690225HCID 86690225, compound

Procedure

1-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-3-p-tolylurea was synthesized using 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (from intermediate D, Example 10) (66 mg, 0.22 mmol) and 1-isocyanato-4-methylbenzene (29.4 mg, 0.22 mmol) according to General Procedure G to give 30 mg (31.4%) of white solid. Anal. Calcd. for C26H33N5O m/z 431.3, found: 432.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.38 (m, 2H), 7.39 (d, J=8.9 Hz, 2H), 7.25 (m, 2H), 7.03 (d, J=8.3 Hz, 2H), 6.93 (d, J=7.6 Hz, 2H), 6.02 (s, 1H), 3.81 (m, 2H), 2.22 (s, 3H), 1.91 (m, 3H), 1.64 (m, 4H), 1.48 (m, 2H), 1.2 (m, 5H), 1.19 (m, 1H).

Sources & evidence

ORD record
ord-7d9b562a79394593a67566d44537e28f
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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