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 1098381Notes

Reaction equation

HRID 1098381 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-a01ac25740964a1c9fd1d5a5325779c2
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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