Hydrochloric Acid → HCID 86691733, compound

HRID 1426941Notes

Reaction equation

HRID 1426941 reaction equation
O=P(Cl)(Cl)Cl.[F:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([C@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]2[CH:24]=[CH:23][N:22]3[N:25]=[CH:26][CH:27]=[C:21]3[N:20]=2)[CH:8]=1.[OH-:28].[Na+].Cl.[CH2:31](Cl)Cl>CN(C=O)C>[F:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([C@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19]2[CH:24]=[CH:23][N:22]3[N:25]=[CH:26][C:27]([CH:31]=[O:28])=[C:21]3[N:20]=2)[CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 67471102HCID 67471102, compound

Product 1

HCID 86691733HCID 86691733, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After POCl3 (221 μL, 2.41 mmol) was added drop-wise to a DMF (4 mL) solution of (R)-4-fluoro-2-(1-(pyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)phenol (600 mg, 2.01 mmol) at ambient temperature, the reaction was stirred for 5 minutes before NaOH (804 mg, 10.1 mmol) was introduced. The reaction was stirred for another 10 minutes before HCl (4 N dioxane, 3 mL) was added, followed by DCM (50 mL). After filtering through Celite®, the reaction was concentrated and purified by reverse-phase column chromatography, eluting with 0-70% acetonitrile/H2O to provide (R)-5-(2-(5-fluoro-2-hydroxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (524 mg, 80% yield) as beige solid. MS (apci) m/z=327.2 (M+H).

Workup

  1. additionwas introduced
  2. additionwas added
  3. filtrationAfter filtering through Celite®
  4. concentrationthe reaction was concentrated
  5. custompurified by reverse-phase column chromatography
  6. washeluting with 0-70% acetonitrile/H2O

Sources & evidence

ORD record
ord-dd3d08740c9f4679862e247e90c46ad0
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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