Hydrochloric Acid → HCID 66847784, compound

HRID 1631345Notes

Reaction equation

HRID 1631345 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@H:9]1[N:13]([C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]([O:25]CC)=[O:24])=[C:16]3[N:15]=2)[C:12]([CH3:29])([CH3:28])[CH2:11][CH2:10]1.[OH-].[Na+].Cl>CO.[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@H:9]1[N:13]([C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[C:16]3[N:15]=2)[C:12]([CH3:29])([CH3:28])[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86664571HCID 86664571, compound

Product 1

HCID 66847784HCID 66847784, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(R)-ethyl 5-(5-(2,5-difluorophenyl)-2,2-dimethylpyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (136 mg, 0.340 mmol) was dissolved in MeOH (5.0 mL) and 1N NaOH (3.40 mL, 3.40 mmol) was added. The reaction was stirred at ambient temperature for 5 days and then heated at reflux for 4 hours. The reaction mixture was cooled, poured onto a mixture of brine (10 mL) and 2N HCl (5 mL) and extracted with DCM. The combined organic extracts were filtered through PS paper and concentrated to provide the title compound (123 mg, 97% yield) as a beige solid. MS (apci) m/z=373.0 (M+H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with DCM
  5. filtrationThe combined organic extracts were filtered through PS paper
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-350bd349b06542788116675342a75e2d
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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