Water → HCID 86668981, compound

HRID 242202Notes

Reaction equation

HRID 242202 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH:5]([CH3:25])[C:6]([C:8]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[F:21])[N:11]=[C:10]([CH3:22])[C:9]=1[C:23]#[N:24])=[O:7].C(O)(C(F)(F)F)=O.O>C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+].C(Cl)Cl>[F:21][C:14]1[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=1[N:12]1[C:8]([C:6](=[O:7])[CH:5]([CH3:25])[CH2:4][CH:3]=[O:2])=[C:9]([C:23]#[N:24])[C:10]([CH3:22])=[N:11]1

Participants

7

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 67120050HCID 67120050, compound

Product 1

HCID 86668981HCID 86668981, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 5-(4,4-dimethoxy-2-methylbutanoyl)-1-(2-fluoro-4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (33 mg, 0.09 mmol) in CHCl3 (1.5 mL) was added TFA (0.4 mL) and water (0.4 mL) and the reaction was stirred 3 h at room temperature. The mixture was diluted with saturated aqueous solution of NaHCO3 and CH2Cl2. The organic phase was separated and the aqueous phase was extracted with CH2Cl2. The organic phase was then washed with saturated aqueous solution of NaHCO3. The combined extracts were dried with a phase separator and concentrated. The desired 1-(2-fluoro-4-methoxyphenyl)-3-methyl-5-(2-methyl-4-oxobutanoyl)-1H-pyrazole-4-carbonitrile (29 mg, 100%) was obtained and used immediately in the next step.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase was extracted with CH2Cl2
  3. washThe organic phase was then washed with saturated aqueous solution of NaHCO3
  4. customThe combined extracts were dried with a phase separator
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e3936e58a5c94334ae31c7a46cdfe970
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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