4-Fluorophenyl isocyanate → HCID 44553790, compound

HRID 1895948Notes

Reaction equation

HRID 1895948 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[F:11][C:12]([F:32])([F:31])[O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2([N:23]3[CH2:28][CH2:27][CH:26]([O:29][NH2:30])[CH2:25][CH2:24]3)[CH2:22][CH2:21]2)=[CH:16][CH:15]=1>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:30][O:29][CH:26]2[CH2:27][CH2:28][N:23]([C:20]3([C:17]4[CH:18]=[CH:19][C:14]([O:13][C:12]([F:11])([F:31])[F:32])=[CH:15][CH:16]=4)[CH2:21][CH2:22]3)[CH2:24][CH2:25]2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 67118420HCID 67118420, compound

Product 1

HCID 44553790HCID 44553790, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Fluorophenyl isocyanate (0.062 ml, 0.546 mmol) was added to a solution of O-(1-(1-(4-(trifluoromethoxy)phenyl)cyclopropyl)piperidin-4-yl)hydroxylamine (157 mg, 0.496 mmol) in tetrahydrofuran (5 ml) and the whole was stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (ethyl acetate/hexane: 25/75 to 45/55) to give 1-(4-fluorophenyl)-3-(1-(1-(4-(trifluoromethoxy)phenyl)cyclopropyl)piperidin-4-yloxy)urea (221 mg, 98%) as a white solid: LCMS: 454 [M+1]+. 1H NMR (DMSO-d6) δ: 0.76 (s, 2H), 0.88 (s, 2H), 1.59 (m, 2H), 1.84 (m, 2H), 2.08 (m, 2H), 2.81 (m, 2H), 3.48 (m, 1H), 5.47 (s, 1H), 7.08 (m, 2H), 7.30 (m, 2H), 7.38 (m, 2H), 7.51 (m, 2H), 8.49 (s, 1H), 9.30 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (ethyl acetate/hexane: 25/75 to 45/55)

Sources & evidence

ORD record
ord-7d71b04d46b34d39bbf86158d83f25ac
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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