Methanol → HCID 69583862, compound

HRID 1790375Notes

Reaction equation

HRID 1790375 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[N:9][NH:10][C:11]=2[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:3][CH:2]=1.OS(O)(=O)=O.[CH3:30]O>>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)=[N:9][NH:10][C:11]=2[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:30])=[O:16])=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 11267326HCID 11267326, compound

Product 1

HCID 69583862HCID 69583862, compound

Procedure

To a solution of 4-(4-(4-pyridyl)-3-(4-fluorophenyl)pyrazolyl)butyric acid (Example C-130) (40 g, 123 mmol) in 650 mL of MeOH was added 20 mL of concentrated H2SO4. The solution was stirred overnight at room temperature. The solution was concentrated and diluted with 200 mL of water. The solution was cooled with an ice/water bath and to the solution was added 150 mL of saturated NaHCO3. The solution was neutralized further with 50% NaOH to pH 7. The resulting slurry was extracted with CH2Cl2 (3×250 mL). The combined extracts were washed with water (1×300 mL) and saturated NaHCO3 (1×500 mL). The organic phase was dried over Na2SO4, filtered and concentrated to afford methyl 4-(4-(4-pyridyl)-3-(4-fluorophenyl)pyrazolyl)butyrate: MS (M+H); 340 (base peak).

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with 200 mL of water
  3. temperatureThe solution was cooled with an ice/water bath and to the solution
  4. additionwas added 150 mL of saturated NaHCO3
  5. extractionThe resulting slurry was extracted with CH2Cl2 (3×250 mL)
  6. washThe combined extracts were washed with water (1×300 mL) and saturated NaHCO3 (1×500 mL)
  7. dry with materialThe organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b33be114347149539f4155a63f188620
Source dataset
uspto-grants-2006_07
Patent number
US07071198B1

Reaction notes

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