4-Fluorophenyl isocyanate → HCID 71227036, compound

HRID 2370010Notes

Reaction equation

HRID 2370010 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].[F:36][C:37]1[CH:42]=[CH:41][C:40]([N:43]=C=O)=[CH:39][CH:38]=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:23]([NH:43][C:40]3[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=3)=[O:35])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 71226691N-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-2-(1-methyl-1H-indol-3-yl)acetamide2×

Product 1

HCID 71227036HCID 71227036, compound

Procedure

1-((1R,2R)-2-((S)-1-(4-Cyanophenyl)piperidin-3-ylamino)cyclohexyl)-3-(4-fluorophenyl)urea was synthesized using 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (from intermediate D, Example 10) (44.5 mg, 0.15 mmol) and 1-fluoro-4-isocyanatobenzene (20.4 mg, 0.15 mmol) according to General Procedure G to give 46 mg (70.8%) of pale yellow solid. Anal. Calcd. for C25H30FN5O m/z 435.2, found: 436.2 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.52 (s, 1H), 7.41 (m, 4H), 7.06 (t, J=8.9 Hz, 2H), 6.93 (d, J=9.1 Hz, 2H), 6.05 (d, J=7.8 Hz, 1H), 3.88 (d, J=11.6 Hz, 1H), 3.76 (d, J=12.7 Hz, 1H), 3.26 (m, 1H), 2.79 (m, 1H), 2.59 (m, 1H), 2.42 (m, 1H), 1.89 (m, 1H), 1.68 (m, 3H), 1.60 (m, 1H), 1.46 (m, 1H), 1.22 (m, 4H), 1.11 (m, 1H).

Sources & evidence

ORD record
ord-ce4e27cf5e0d4e038296ec128fb183fa
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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