2-(2,2-difluoropropylamino)ethanol → HCID 58763944, compound

HRID 859189Notes

Reaction equation

HRID 859189 reaction equation
C(O[C:4]([C:6]1[C:10]([OH:11])=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[N:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[N:7]=1)=[O:5])C.[F:26][C:27]([F:34])([CH3:33])[CH2:28][NH:29][CH2:30][CH2:31][OH:32]>C(OCC)(=O)C>[F:26][C:27]([F:34])([CH3:33])[CH2:28][N:29]([CH2:30][CH2:31][OH:32])[C:4]([C:6]1[C:10]([OH:11])=[C:9]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[N:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[N:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 27583572-(2,2-difluoropropylamino)ethanolHCID 24828929HCID 24828929, compound

Product 1

HCID 58763944HCID 58763944, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
125 °C

Procedure

A stirred mixture of 1-(2-chloro-phenyl)-5-(4-chloro-phenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid ethyl ester I-3c (15 g, 40 mmol) and 2-(2,2-difluoro-propylamino)-ethanol (16.5 g, 120 mmol) were heated at 125° C. for 18 hours. The reaction solution was cooled, diluted into ethyl acetate, washed with 1 N aq. HCl, brine, dried (Na2SO4) and concentrated in vacuo. The resulting oil was chromatographed on silica gel (20% to 40% ethyl acetate/hexanes) to afford the title compound (I-3d) as an oil, 10 g.

Workup

  1. temperatureThe reaction solution was cooled
  2. washwashed with 1 N aq. HCl, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was chromatographed on silica gel (20% to 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-deaa33591059447cac60b90a1235a793
Source dataset
uspto-grants-2006_12
Patent number
US07151097B2

Reaction notes

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