Methanol → HCID 45137106, compound

HRID 2198104Notes

Reaction equation

HRID 2198104 reaction equation
COC(=O)C[CH2:5][S:6]([C:9]1[CH:14]=[C:13]([CH2:15][NH:16][C:17]([C:19]2[C:20]3[CH:27]=[N:26][N:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:21]=3[CH:22]=[N:23][CH:24]=2)=[O:18])[CH:12]=[CH:11][N:10]=1)(=[O:8])=[O:7].C[O-].[Na+].CO.IC[C:43]([O:45][CH2:46][CH3:47])=[O:44]>CS(C)=O.O>[CH2:46]([O:45][C:43](=[O:44])[CH2:5][S:6]([C:9]1[CH:14]=[C:13]([CH2:15][NH:16][C:17]([C:19]2[C:20]3[CH:27]=[N:26][N:25]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[C:21]=3[CH:22]=[N:23][CH:24]=2)=[O:18])[CH:12]=[CH:11][N:10]=1)(=[O:8])=[O:7])[CH3:47]

Participants

7

Reactant 4

HCID 887MethanolHCID 12183Ethyl iodoacetateHCID 10942334Sodium MethoxideHCID 59278102HCID 59278102, compound

Product 1

HCID 45137106HCID 45137106, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 3-[4-({[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-methyl)-pyridine-2-sulfonyl]-propionic acid methyl ester (200 mg, 0.4 mmol) in DMSO (5 mL) was treated a 15% solution of sodium methoxide in methanol (150 μL, 0.42 mmol). After 15 minutes, the mixture was cooled (water bath) and ethyl iodoacetate (50 μL, 0.42 mmol) was added followed by removal of the water bath. After 18 hours, the mixture was diluted with EtOAc (30 mL) and water (30 mL) and the organic layer was separated. The aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were washed with water (20 mL), dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography using a gradient of 0-6% methanol in dichloromethane. The material from the column was twice triturated with ether, filtered and dried under vacuum to afford the title compound as a tan solid.

Workup

  1. additionwas added
  2. customfollowed by removal of the water bath
  3. waitAfter 18 hours
  4. additionthe mixture was diluted with EtOAc (30 mL) and water (30 mL)
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  7. washThe combined organic layers were washed with water (20 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel chromatography
  12. customThe material from the column was twice triturated with ether
  13. filtrationfiltered
  14. customdried under vacuum

Sources & evidence

ORD record
ord-bf108cf073b54617b1c1cc662788b8bb
Source dataset
uspto-grants-2012_12
Patent number
US08338610B2

Reaction notes

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