Methane, dichloromethoxy- → Cyclopropylmethyl [3-methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetate

HRID 888728Notes

Reaction equation

HRID 888728 reaction equation
ClC(Cl)OC.[CH3:6][C:7]1[C:11]([CH2:12][C:13]([OH:15])=[O:14])=[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:9]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][C:27]=2[CH3:28])[N:8]=1.[CH:29]1([CH2:32]O)[CH2:31][CH2:30]1>>[CH3:6][C:7]1[C:11]([CH2:12][C:13]([O:15][CH2:32][CH:29]2[CH2:31][CH2:30]2)=[O:14])=[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:9]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][C:27]=2[CH3:28])[N:8]=1

Participants

4

Reactant 3

HCID 21004Methane, dichloromethoxy-2×HCID 75644CyclopropanemethanolHCID 68818330[3-Methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetic acid

Product 1

HCID 86626936Cyclopropylmethyl [3-methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetate

Conditions

Temperature
60 °C

Procedure

0.296 g (2.575 mmol) of dichloro(methoxy)methane was added to 0.175 g (0.569 mmol) [3-methyl-1-(4-methylpyridin-3-yl)-5-phenyl-1H-pyrazol-4-yl]acetic acid, and the mixture was stirred at 60° C. for 2 h. Excess dichloro(methoxy)methane was removed under reduced pressure, 0.660 g (9.153 mmol) of cyclopropylmethanol was added to the residue and the mixture was stirred at 20° C. for 0.5 h. The solvent was removed under reduced pressure, a mixture of 10 ml of dichloromethane, 1.5 ml of diisopropylethylamine and 10 ml of water was added to the residue and the aqueous phase was extracted with 15 ml of dichloromethane. The combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. Chromatography of the residue gave 0.123 g (59% of theory) of a colorless solid of m.p. 87° C.

Workup

  1. additionwas added to the residue
  2. stirringthe mixture was stirred at 20° C. for 0.5 h
  3. customThe solvent was removed under reduced pressure
  4. additiona mixture of 10 ml of dichloromethane, 1.5 ml of diisopropylethylamine and 10 ml of water
  5. additionwas added to the residue
  6. extractionthe aqueous phase was extracted with 15 ml of dichloromethane
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customChromatography of the residue gave 0.123 g (59% of theory) of a colorless solid of m.p. 87° C.

Sources & evidence

ORD record
ord-9406ec11a99d45039d9c8c9b5476d26d
Source dataset
uspto-grants-2012_08
Patent number
US08252723B2

Reaction notes

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