Trichloroacetyl chloride → HCID 59420863, compound

HRID 499206Notes

Reaction equation

HRID 499206 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[C:19]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH:18]=[C:17]([F:28])[CH:16]=2)=[O:13])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:36][C:37]([Cl:42])([Cl:41])[C:38](Cl)=[O:39]>ClCCl>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[C:19]([O:21][CH:22]3[CH2:23][CH2:24][N:25]([C:38](=[O:39])[C:37]([Cl:42])([Cl:41])[Cl:36])[CH2:26][CH2:27]3)[CH:18]=[C:17]([F:28])[CH:16]=2)=[O:13])[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 68457459HCID 68457459, compound

Product 1

HCID 59420863HCID 59420863, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

To an ice-water cooled solution of 1-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3-{3-fluoro-5-(piperidin-4-yloxy)-phenyl}-urea (390.6 mg, 1.0 mmol) and triethylamine (280 μL, mmol) in dichloromethane (5 mL) is added trichloroacetyl chloride (115 μL, 1.0 mmol). The reaction mixture is allowed to warm up to 22° C. and stirred for 1 hour. After removal of solvent, the residue is purified on a silica gel chromatography with hexanes and ethyl acetate to provide a white solid (520.0 mg, 97% yield, ES+(m/z) 535.9 [M+H]).

Workup

  1. customAfter removal of solvent
  2. customthe residue is purified on a silica gel chromatography with hexanes and ethyl acetate
  3. customto provide a white solid (520.0 mg, 97% yield, ES+(m/z) 535.9 [M+H])

Sources & evidence

ORD record
ord-f1116932e2c64a2fa053ce9bd039af6e
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

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