Potassium Hydroxide → HCID 57963266, compound

HRID 1690008Notes

Reaction equation

HRID 1690008 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[CH:4]=[N:3][CH:2]=1.[F:10][C:11]1[C:16]([CH:17]=[O:18])=[C:15]([F:19])[CH:14]=[CH:13][C:12]=1[NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22].[OH-].[K+].[Cl-].[NH4+]>O.CO>[F:10][C:11]1[C:16]([CH:17]([OH:18])[C:9]2[C:5]3[CH:4]=[N:3][CH:2]=[N:1][C:6]=3[NH:7][CH:8]=2)=[C:15]([F:19])[CH:14]=[CH:13][C:12]=1[NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 2615917H-Pyrrolo(2,3-d)pyrimidineHCID 53419003N-(2,4-Difluoro-3-formylphenyl)-1-propanesulfonamide

Product 1

HCID 57963266HCID 57963266, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 7H-pyrrolo[2,3-d]pyrimidine (6, 0.100 g, 0.839 mmol) and propane-1-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide (9, 0.258 g, 0.982 mmol), 1.4 mL of methanol was added. This suspension was allowed to stir for 10 minutes, followed by the addition of potassium hydroxide (0.153 g, 2.73 mmol). The reaction was allowed to stir at room temperature for 8 hours, then poured into 5 mL of water and 5 mL of saturated ammonium chloride and extracted with 2×5 mL of ethyl acetate. Organic layers were combined and concentrated under vacuum and the resulting residue was purified by silica gel column chromatography eluting with a gradient of 60 to 100% ethyl acetate in hexanes. Appropriate fractions were combined and concentrated under vacuum to give the desired compound (P-0001, 150 mg), with some 7H-pyrrolo[2,3-d]pyrimidine impurity, used in the next step without further purification. MS(ESI)[M+H+]+=383.2, [M−H+]−=381.5.

Workup

  1. stirringto stir at room temperature for 8 hours
  2. extractionextracted with 2×5 mL of ethyl acetate
  3. concentrationconcentrated under vacuum
  4. customthe resulting residue was purified by silica gel column chromatography
  5. washeluting with a gradient of 60 to 100% ethyl acetate in hexanes
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-915b99d4da9744cc86dc8439fcc3e7e0
Source dataset
uspto-grants-2012_04
Patent number
US08153641B2

Reaction notes

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