Sodium Hydroxide → HCID 66852813, compound

HRID 1631340Notes

Reaction equation

HRID 1631340 reaction equation
[C:1]([NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][C@H:20]([OH:22])[CH2:19][C@@H:18]3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)=[N:13][C:12]=12)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[C:1]([NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][C:20](=[O:22])[CH2:19][C@@H:18]3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)=[N:13][C:12]=12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 66851763HCID 66851763, compound

Product 1

HCID 66852813HCID 66852813, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

N-tert-butyl-5-((2R,4R)-2-(3-fluorophenyl)-4-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (Example 42, 10 mg, 0.025 mmol) and the Dess-Martin reagent (16 mg, 0.038 mmol) in DCM (2.0 mL) were stirred at ambient temperature overnight. 1N NaOH (2.5 mL) was added and the reaction stirred for 30 minutes. Brine (2.5 mL) was added and the reaction was filtered through a phase separator frit, washing with several portions of DCM. The DCM solution was concentrated and the residue purified by reverse phase chromatography (20-70% acetonitrile/water) to provide the title compound (2.7 mg, 27% yield) as a clear oil. MS (apci) m/z=396.0 (M+H).

Workup

  1. filtrationthe reaction was filtered through a phase separator frit
  2. washwashing with several portions of DCM
  3. concentrationThe DCM solution was concentrated
  4. customthe residue purified by reverse phase chromatography (20-70% acetonitrile/water)

Sources & evidence

ORD record
ord-74ec6e602bea45659f68bc6faa292656
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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