Water → HCID 59774842, compound

HRID 2387268Notes

Reaction equation

HRID 2387268 reaction equation
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[CH:5]=[CH:4][C:3]=1[NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13].[CH:18]1([O:23][C:24]2[CH:25]=[C:26]3[CH:32]=[CH:31][NH:30][C:27]3=[N:28][CH:29]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1.[OH-].[K+].O>CO>[CH:18]1([O:23][C:24]2[CH:25]=[C:26]3[C:32]([CH:8]([OH:9])[C:7]4[C:2]([F:1])=[C:3]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[CH:4]=[CH:5][C:6]=4[F:10])=[CH:31][NH:30][C:27]3=[N:28][CH:29]=2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 53419003N-(2,4-Difluoro-3-formylphenyl)-1-propanesulfonamideHCID 59774804HCID 59774804, compound

Product 1

HCID 59774842HCID 59774842, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (10, 102 mg, 0.32 mmol) in methanol (1.5 mL) was added 5-cyclopentyloxy-1H-pyrrolo[2,3-b]pyridine (P-0001, 65 mg, 0.32 mmol, prepared as described in Example 12) and potassium hydroxide (54 mg, 0.96 mmol) under an atmosphere of nitrogen. The reaction was stirred at room temperature for 3 hours. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and filtrated. The filtrate was concentrated and purified by silica gel column chromatography eluting with 50% ethyl acetate in hexane to give a solid (11, 102 mg, 68%). MS (ESI) [M+H+]+=466.2.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 50% ethyl acetate in hexane
  8. customto give a solid (11, 102 mg, 68%)

Sources & evidence

ORD record
ord-ceb74580cad044a685b99db55cef345e
Source dataset
uspto-grants-2012_09
Patent number
US08268858B2

Reaction notes

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