p-(Trifluoromethoxy)phenyl isocyanate → HCID 71227183, compound

HRID 2369972Notes

Reaction equation

[N:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1)=[C:2]=[O:3].[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][CH2:27][CH:26]([NH:30][C@@H:31]3[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]3[NH2:37])[CH2:25]2)=[CH:20][CH:19]=1)([O-:17])=[O:16]>>[N+:15]([C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30][C@@H:31]3[CH2:36][CH2:35][CH2:34][CH2:33][C@H:32]3[NH:37][C:2]([NH:1][C:4]3[CH:9]=[CH:8][C:7]([O:10][C:11]([F:12])([F:13])[F:14])=[CH:6][CH:5]=3)=[O:3])[CH2:25]2)=[CH:22][CH:23]=1)([O-:17])=[O:16]

Participants

Reactant 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanate

HCID 71233239HCID 71233239, compound

Product 1

HCID 71227183HCID 71227183, compoundYield 38.3%

Procedure

1-((1R,2R)-2-((S)-1-(4-Nitrophenyl)piperidin-3-ylamino)cyclohexyl)-3-(4-(trifluoromethoxy)phenyl)urea was synthesized as described in General Procedure G, using 1-isocyanato-4-(trifluoromethoxy)benzene (15.31 mg, 0.075 mmol) and (1R,2R)—N1-(1-(4-nitrophenyl)piperidin-3-yl)cyclohexane-1,2-diamine (24 mg, 0.075 mmol) to give 15 mg (30% yield) of the title compound as a yellow solid. Anal. Calcd. for C25H30F3N5O4 m/z 521.5, found: 522.3 (M+H)+; 1H NMR (500 MHz, CDCl3) δ ppm 7.77 (d, J=8.80 Hz, 2H), 7.22 (d, J=8.80 Hz, 2H), 6.99 (d, J=8.25 Hz, 2H), 6.67 (d, J=8.80 Hz, 2H), 3.67 (br. s., 1H), 3.63-3.56 (m, 1H), 3.56-3.49 (m, 1H), 3.29 (br. s., 3H), 3.07-2.96 (m, 1H), 2.11-2.20 (m, 2H), 1.99-1.58 (m, 7H), 1.43 (d, J=12.65 Hz, 1H), 1.30-1.12 (m, 2H).

Workup

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

Sources & evidence

ORD record: ord-85ee07cdf25343f2b4f6967bbb071db3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710049B2

Reaction notes

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