4-(Trifluoromethyl)phenyl isocyanate → HCID 71226438, compound

HRID 2369971Notes

Reaction equation

HRID 2369971 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][CH:4]=1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH:25]([NH:29][C@@H:30]3[CH2:35][CH2:34][CH2:33][CH2:32][C@H:31]3[NH2:36])[CH2:24]2)=[CH:19][CH:18]=1)([O-:16])=[O:15]>>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][C@H:25]([NH:29][C@@H:30]3[CH2:35][CH2:34][CH2:33][CH2:32][C@H:31]3[NH:36][C:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:12])([F:13])[F:1])=[CH:8][CH:7]=3)=[O:11])[CH2:24]2)=[CH:21][CH:22]=1)([O-:16])=[O:15]

Participants

3

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 71233239HCID 71233239, compound

Product 1

HCID 71226438HCID 71226438, compoundYield 54%

Procedure

1-((1R,2R)-2-((S)-1-(4-Nitrophenyl)piperidin-3-ylamino)cyclohexyl)-3-(4-(trifluoromethyl)phenyl)urea was synthesized as described in General Procedure F using 4-trifluoromethyl-phenyl isocyanate (13 mg, 0.069 mmol) and (1R,2R)—N1-(1-(4-nitrophenyl)piperidin-3-yl)cyclohexane-1,2-diamine (30 mg, 0.069 mmol) to give 1-((1R,2R)-2-((S)-1-(4-nitrophenyl)piperidin-3-ylamino)cyclohexyl)-3-(4-(trifluoromethyl)phenyl)urea as a yellow solid (2.0 mg, 54% yield). Anal. Calcd. for C25H30F3N5O3 m/z 505.5, found: 506.3 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 9.61-8.86 (m, 1H), 8.76 (br. s., 1H), 7.72 (d, J=8.80 Hz, 2H), 7.42-7.33 (m, 2H), 7.30 (d, J=8.25 Hz, 2H), 7.06 (br. s., 1H), 6.66 (d, J=8.80 Hz, 2H), 3.75-3.56 (m, 2H), 3.48 (d, J=12.65 Hz, 1H), 3.44-3.29 (m, 2H), 3.25 (d, J=7.70 Hz, 1H), 3.11 (br. s., 1H), 2.24-2.00 (m, 4H), 1.86 (d, J=13.20 Hz, 3H), 1.84-1.75 (m, 1H), 1.71 (d, J=11.00 Hz, 1H), 1.49 (br. s., 1H) 1.37-1.17 (m, 2H); 13C NMR (126 MHz, CDCl3) δ ppm 154.35, 144.05, 125.87, 125.55, 123.02, 120.76, 117.83, 114.19, 66.81, 63.17, 52.86, 52.53, 48.20, 31.08, 28.87, 26.95, 23.72, 22.69, 21.03.

Workup

  1. custom1-((1R,2R)-2-((S)-1-(4-Nitrophenyl)piperidin-3-ylamino)cyclohexyl)-3-(4-(trifluoromethyl)phenyl)urea was synthesized

Sources & evidence

ORD record
ord-0626509b92244f4087ea1d5bd0a902c7
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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