Benzene, 1-chloro-3-isocyanato- → HCID 71227154, compound

HRID 2370017Notes

Reaction equation

HRID 2370017 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].[Cl:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([N:43]=C=O)[CH:38]=1>>[Cl:36][C:37]1[CH:38]=[C:39]([NH:43][C:23]([NH:22][C@@H:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C@H:16]2[NH:15][C@H:11]2[CH2:12][CH2:13][CH2:14][N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)[CH2:10]2)=[O:35])[CH:40]=[CH:41][CH:42]=1

Participants

3

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 71226691HCID 71226691, compound2×

Product 1

HCID 71227154HCID 71227154, compound

Procedure

1-(3-Chlorophenyl)-3-((1R,2R)-2-((S)-1-(4-cyanophenyl)piperidin-3-ylamino)cyclohexyl)urea was synthesized using 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (from intermediate D, Example 10) (60 mg, 0.20 mmol) and 1-chloro-3-isocyanatobenzene (30.9 mg, 0.20 mmol) according to General Procedure G to give 20 mg (22%) of a white solid. Anal. Calcd. for C25H30ClN5O m/z 451.2, found: 452.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.00 (s, 1H), 7.66 (s, 1H), 7.43 (d, J=8.9 Hz, 2H), 7.24 (t, J=8.0 Hz, 1H), 7.17 (d, J=8 Hz, 1H), 6.95 (m, 3H), 6.45 (bs, 1H), 3.88 (d, J=11.3 Hz, 1H), 3.72 (d, J=12.6 Hz, 1H), 2.84 (m, 4H), 1.97 (m, 4H), 1.68 (m, 3H), 1.50 (m, 4H), 1.25 (m, 2H).

Sources & evidence

ORD record
ord-5cf66cda9b0344f8ad1989165b062b33
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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