Hydrochloric Acid → HCID 66847957, compound

HRID 1631405Notes

Reaction equation

HRID 1631405 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[N:12]([C:13]3[CH:18]=[CH:17][N:16]4[N:19]=[CH:20][C:21]([C:22]([O:24]CC)=[O:23])=[C:15]4[N:14]=3)[C@@:11]([CH2:28][OH:29])([CH3:27])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[N:12]([C:13]3[CH:18]=[CH:17][N:16]4[N:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[C:15]4[N:14]=3)[C@@:11]([CH2:28][OH:29])([CH3:27])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66847776HCID 66847776, compound

Product 1

HCID 66847957HCID 66847957, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 5-((2S,5R)-5-(5-fluoropyridin-3-yl)-2-(hydroxymethyl)-2-methylpyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (52.0 mg, 0.130 mmol) and NaOH (26.0 mg, 0.325 mmol) in MeOH (1.0 mL) was stirred at ambient temperature for 60 hours. The reaction was treated with HCl (4 N dioxane, 163 μL, 0.651 mmol) and concentrated. The residue was treated with DCM and filtered through Celite. The solution was concentrated to afford 5-((2S,5R)-5-(5-fluoropyridin-3-yl)-2-(hydroxymethyl)-2-methylpyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (29 mg, 60% yield) as a white solid. MS (apci) m/z=372.0 (M+H).

Workup

  1. concentrationconcentrated
  2. additionThe residue was treated with DCM
  3. filtrationfiltered through Celite
  4. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-8aba1b25c7e340af9ec2f7e1724f60f1
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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