Potassium Hydroxide → propane-1-sulfonic acid {2,4-difluoro-3-[hydroxy-(5-phenylamino-1H-pyrrolo[2,3-b]-pyridin-3-yl)-methyl]-phenyl}-amide

HRID 250566Notes

Reaction equation

HRID 250566 reaction equation
[C:1]1([NH:7][C:8]2[CH:9]=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[F:19][C:20]1[C:25]([CH:26]=[O:27])=[C:24]([F:28])[CH:23]=[CH:22][C:21]=1[NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31]>CO>[F:19][C:20]1[C:25]([CH:26]([OH:27])[C:16]2[C:10]3[C:11](=[N:12][CH:13]=[C:8]([NH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:9]=3)[NH:14][CH:15]=2)=[C:24]([F:28])[CH:23]=[CH:22][C:21]=1[NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 53419003N-(2,4-Difluoro-3-formylphenyl)-1-propanesulfonamideHCID 57595745n-Phenyl-1h-pyrrolo[2,3-b]pyridin-5-amine

Product 1

HCID 58086341propane-1-sulfonic acid {2,4-difluoro-3-[hydroxy-(5-phenylamino-1H-pyrrolo[2,3-b]-pyridin-3-yl)-methyl]-phenyl}-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To phenyl-(-1H-pyrrolo[2,3-b]pyridine-5-yl)-amine (70, 17.0 mg, 0.09 mmol) in methanol (5.0 mL) were added potassium hydroxide (92.0 mg, 1.6 mmol) and propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (73, 19.0 mg, 0.072 mmol, prepared as described in Example 7) under an atmosphere of nitrogen. The reaction was stirred for 12 hours at room temperature. The reaction was concentrated and purified by silica gel column chromatography eluting with 1% methanol in dichloromethane to give the compound (71, 17 mg, 50%). MS (ESI) [M+H+]+=473.5.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel column chromatography
  3. washeluting with 1% methanol in dichloromethane
  4. customto give the compound (71, 17 mg, 50%)

Sources & evidence

ORD record
ord-b2ed613572c74335aac6db6376952161
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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