1-Isocyanato-4-methoxybenzene → HCID 71227130, compound

HRID 2370022Notes

Reaction equation

HRID 2370022 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].[N:36]([C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1)=[C:37]=[O:38]>>[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:37]([NH:36][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)=[O:38])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 71226691HCID 71226691, compound2×

Product 1

HCID 71227130HCID 71227130, compound

Procedure

1-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-3-(4-methoxyphenyl)urea was synthesized using 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (from intermediate D, Example 10) (55 mg, 0.18 mmol) and 1-isocyanato-4-methoxybenzene (27.5 mg, 0.18 mmol) according to General Procedure G to give 20 mg (24.2%) of a white solid. Anal. Calcd. for C26H33N5O2 m/z 447.3, found: 448.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.28 (s, 1H), 7.41 (d, J=9 Hz, 2H), 7.29 (d, J=9 Hz, 2H), 6.92 (d, J=9 Hz, 2H), 6.82 (d, J=3 Hz, 2H), 5.95 (d, J=7.6 Hz, 1H), 3.89 (d, m, 1H), 3.77 (m, 1H), 3.70 (s, 3H), 3.26 (m, 1H), 2.79 (m, 1H), 2.60 (m, 1H), 2.40 (m, 1H), 1.89 (m, 3H), 1.68 (m, 1H), 1.60 (m, 2H), 1.45 (m, 1H), 1.23 (m, 6H), 1.10 (m, 1H).

Sources & evidence

ORD record
ord-7d3182960e0340b18d0b18b12d56b7df
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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