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Water → 1-[2-Acetyl-4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]tetrahydro-1(2H)-pyridazinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

HRID 75175
Notes
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Reaction equation

HRID 75175 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]1[O:13][N:12]=[C:11]([C:14]2[N:15]=[C:16]([CH:19]3[CH2:24][CH2:23][N:22]([C:25](=[O:37])[CH2:26][N:27]4[C:31]([CH3:32])=[CH:30][C:29]([C:33]([F:36])([F:35])[F:34])=[N:28]4)[NH:21][CH2:20]3)[S:17][CH:18]=2)[CH2:10]1.O.[C:39](OC(=O)C)(=[O:41])[CH3:40]>>[C:39]([N:21]1[CH2:20][CH:19]([C:16]2[S:17][CH:18]=[C:14]([C:11]3[CH2:10][CH:9]([C:3]4[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=4[F:8])[O:13][N:12]=3)[N:15]=2)[CH2:24][CH2:23][N:22]1[C:25](=[O:37])[CH2:26][N:27]1[C:31]([CH3:32])=[CH:30][C:29]([C:33]([F:35])([F:36])[F:34])=[N:28]1)(=[O:41])[CH3:40]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 866744671-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]tetrahydro-1(2H)-pyridazinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

Product 1

HCID 866744661-[2-Acetyl-4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]tetrahydro-1(2H)-pyridazinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

Conditions

Temperature
100 °C

Procedure

A mixture of 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3 isoxazolyl]-2-thiazolyl]tetrahydrol(2H)-pyridazinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (i.e. the product of Example 1) (0.24 g, 0.44 mmol) in acetic anhydride (2 mL) was heated at 100° C. overnight. The reaction mixture was cooled, water (30 mL) was added and the mixture was stirred for 30 min and then extracted with ethyl acetate. The ethyl acetate extract was washed with saturated aqueous sodium bicarbonate solution and saturated sodium chloride solution, dried over magnesium sulfatate, filtered, and concentrated under reduced pressure. The resulting material was purified by silica gel chromatography (0-100% gradient of ethyl acetate in hexane as eluant) to provide the title compound (150 mg), a compound of the present invention, as a dark foam.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with saturated aqueous sodium bicarbonate solution and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfatate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting material was purified by silica gel chromatography (0-100% gradient of ethyl acetate in hexane as eluant)

Sources & evidence

ORD record
ord-ad74ab3709834021a4e224070fa4c269
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835427B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes