3,4-Difluorophenyl isocyanate → HCID 10126413, compound

HRID 1182128Notes

Reaction equation

HRID 1182128 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7]2[CH2:10][N:9]([CH2:11][CH2:12][CH2:13][NH2:14])[CH2:8]2)=[CH:4][CH:3]=1.[F:17][C:18]1[CH:19]=[C:20]([N:25]=[C:26]=[O:27])[CH:21]=[CH:22][C:23]=1[F:24]>ClCCl>[F:17][C:18]1[CH:19]=[C:20]([NH:25][C:26]([NH:14][CH2:13][CH2:12][CH2:11][N:9]2[CH2:10][CH:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:16][CH:15]=3)[CH2:8]2)=[O:27])[CH:21]=[CH:22][C:23]=1[F:24]

Participants

4

Reactant 2

HCID 27347083,4-Difluorophenyl isocyanateHCID 69410452HCID 69410452, compound

Product 1

HCID 10126413HCID 10126413, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propylamine (0.04 g, 0.178 mmol) and 3,4-difluorophenylisocyanate (0.020 ml, 0.178 mmol) in dichloromethane (1 ml) is stirred at room temperature for 5 hours. The solvent is evaporated and the crude product purified by flash silica chromatography (elution gradient a 3:97 to 5:95 methanol/dichloromethane) to afford 1-(3,4-difluoro-phenyl)-3-{3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propyl}-urea. [MH]+ 379.9.

Workup

  1. customThe solvent is evaporated
  2. customthe crude product purified by flash silica chromatography (
  3. washelution gradient a 3:97 to 5:95 methanol/dichloromethane)

Sources & evidence

ORD record
ord-243e397ce547461ca743680833cbccf5
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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