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Water → N-{2-fluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-4-trifluoromethyl-benzenesulfonamide

HRID 1690028
Notes
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Reaction equation

HRID 1690028 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]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[N:24]1[C:29]2[NH:30][CH:31]=[CH:32][C:28]=2[CH:27]=[N:26][CH:25]=1.[OH-].[K+].O>CO>[F:1][C:2]1[C:7]([CH:8]([OH:9])[C:32]2[C:28]3[CH:27]=[N:26][CH:25]=[N:24][C:29]=3[NH:30][CH:31]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][CH:15]=1)(=[O:13])=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 2615917H-Pyrrolo(2,3-d)pyrimidineHCID 57963257N-(2-fluoro-3-formyl-phenyl)-4-trifluoromethyl-benzenesulfonamide

Product 1

HCID 57963304N-{2-fluoro-3-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-phenyl}-4-trifluoromethyl-benzenesulfonamideYield 44%

Reagents, catalysts & solvents

1
HCID 887MethanolSolvent

Procedure

To N-(2-fluoro-3-formyl-phenyl)-4-trifluoromethyl-benzenesulfonamide (34, 172 mg, 0.50 mmol) in 1 mL of methanol, 7H-pyrrolo[2,3-d]pyrimidine (6, 71 mg, 0.60 mmol) and potassium hydroxide (84 mg, 1.5 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 the residue was 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-0034, 101 mg, 44%). MS(ESI) [M+H+]−=467.8.

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. customthe residue was purified by silica gel column chromatography
  7. washeluting with 5% methanol in dichloromethane
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f83aa60b48b04475a868b075aeafc922
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08153641B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes