Water → HCID 57963310, compound

HRID 1690017Notes

Reaction equation

HRID 1690017 reaction equation
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12].[N:17]1[C:22]2[NH:23][CH:24]=[CH:25][C:21]=2[CH:20]=[N:19][CH:18]=1.[OH-].[K+].O>CO>[F:1][C:2]1[C:7]([CH:8]([OH:9])[C:25]2[C:21]3[CH:20]=[N:19][CH:18]=[N:17][C:22]=3[NH:23][CH:24]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 2615917H-Pyrrolo(2,3-d)pyrimidineHCID 58086814Propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide

Product 1

HCID 57963310HCID 57963310, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide (18.75 mg, 0.30 mmol) in 0.6 mL of methanol, 7H-pyrrolo[2,3-d]pyrimidine (6, 73 mg, 0.61 mmol) and potassium hydroxide (51 mg, 0.92 mmol) were added under an atmosphere of nitrogen. The reaction was stirred at room temperature for 24 hours, then poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and filtered. The filtrate was concentrated under vacuum and purified by silica gel column chromatography eluting with 5% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a solid (P-0005, 85 mg, 76%). MS(ESI) [M+H+]+=365.1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum
  6. custompurified by silica gel column chromatography
  7. washeluting with 5% methanol in dichloromethane
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-03926bdc31d242538e177a0e9887bb57
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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