Hydrochloric Acid → HCID 66847936, compound

HRID 1631398Notes

Reaction equation

HRID 1631398 reaction equation
C([O:4][C@@H:5]1[CH2:9][N:8]([C:10]2[CH:15]=[CH:14][N:13]3[N:16]=[CH:17][C:18]([C:19]([O:21]CC)=[O:20])=[C:12]3[N:11]=2)[C@@H:7]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)[CH2:6]1)(=O)C.[OH-].[Na+].Cl>CO.O1CCOCC1>[F:30][C:26]1[CH:25]=[C:24]([C@H:7]2[CH2:6][C@H:5]([OH:4])[CH2:9][N:8]2[C:10]2[CH:15]=[CH:14][N:13]3[N:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[C:12]3[N:11]=2)[CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66853015HCID 66853015, compound

Product 1

HCID 66847936HCID 66847936, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 5-((2R,4S)-4-acetoxy-2-(3-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (225 mg, 0.546 mmol) and NaOH (131 mg, 1.64 mmol) in MeOH (1.0 mL) was stirred at ambient temperature for 60 hours followed by 3 hours at 60° C. The mixture was cooled to ambient temperature and 4M HCl in dioxane (1 mL) was added. The mixture was concentrated and the residue was treated with DCM. The mixture was filtered through Celite and concentrated to afford 5-((2R,4S)-2-(3-fluorophenyl)-4-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (188 mg, 10% yield) as a white solid. MS (apci) m/z=343.0 (M+H).

Workup

  1. waitfollowed by 3 hours at 60° C
  2. temperatureThe mixture was cooled to ambient temperature
  3. concentrationThe mixture was concentrated
  4. additionthe residue was treated with DCM
  5. filtrationThe mixture was filtered through Celite
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4911a88041bc4178bc6ba3520d34a387
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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