2,2,2-Trifluoroethanol → HCID 68014918, compound

HRID 1747764Notes

Reaction equation

HRID 1747764 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].F[C:10]1[CH:15]=[C:14]([N:16]2[CH:20]=[CH:19][CH:18]=[N:17]2)[CH:13]=[CH:12][C:11]=1[N:21]1[C:26]2[CH:27]=[CH:28][O:29][C:25]=2[C:24](=[O:30])[C:23]([C:31]2[N:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:34]=[CH:33][CH:32]=2)=[N:22]1.C(=O)([O-])O.[Na+]>CN(C=O)C>[C:36]1([N:35]2[C:31]([C:23]3[C:24](=[O:30])[C:25]4[O:29][CH:28]=[CH:27][C:26]=4[N:21]([C:11]4[CH:12]=[CH:13][C:14]([N:16]5[CH:20]=[CH:19][CH:18]=[N:17]5)=[CH:15][C:10]=4[O:4][CH2:3][C:2]([F:6])([F:5])[F:1])[N:22]=3)=[CH:32][CH:33]=[N:34]2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 89586363HCID 89586363, compound

Product 1

HCID 68014918HCID 68014918, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,2,2-trifluoroethanol (48 mg) in DMF (1 mL) was added 60% NaH (19.2 mg) under ice-cooling. The reaction mixture was stirred at room temperature for 30 min, and 1-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-3-(1-phenyl-1H-pyrazol-5-yl)furo[3,2-c]pyridazin-4(1H)-one (70 mg) was added. The reaction mixture was stirred at 100° C. for 6 hr, and saturated aqueous sodium hydrogen carbonate solution was added. The reaction mixture was extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (45 mg).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at 100° C. for 6 hr
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-ff1ac76a145740c3ad97fe3fc4a82127
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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