Acetyl chloride → HCID 59278182, compound

HRID 559628Notes

Reaction equation

HRID 559628 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:34])[S:5]([C:8]1[CH:33]=[CH:32][C:11]([CH2:12][NH:13][C:14]([C:16]2[C:17]3[CH:24]=[N:23][N:22]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[C:18]=3[CH:19]=[N:20][CH:21]=2)=[O:15])=[CH:10][CH:9]=1)(=[O:7])=[O:6].CCN(CC)CC.[C:42](Cl)(=[O:44])[CH3:43]>ClCCl.CCOC(C)=O>[F:31][C:28]1[CH:29]=[CH:30][C:25]([N:22]2[C:18]3[CH:19]=[N:20][CH:21]=[C:16]([C:14]([NH:13][CH2:12][C:11]4[CH:10]=[CH:9][C:8]([S:5]([N:4]([CH3:34])[CH2:3][CH2:2][O:1][C:42](=[O:44])[CH3:43])(=[O:6])=[O:7])=[CH:33][CH:32]=4)=[O:15])[C:17]=3[CH:24]=[N:23]2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 45138314HCID 45138314, compound

Product 1

HCID 59278182HCID 59278182, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature solution of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid 4-[(2-hydroxy-ethyl)-methyl-sulfamoyl]-benzylamide (50 mg, 0.1 mmol), Et3N (16 μL, 0.14 mmol) in dichloromethane was added acetyl chloride (0.010 mL, 0.11 mmol). After 4 hours, the mixture was diluted with EtOAc and the organic layer was washed with saturated aqueous sodium bicarbonate, 1 N aqueous HCl, water, brine, dried over magnesium sulfate, filtered and concentrated to afford the title compound.

Workup

  1. washthe organic layer was washed with saturated aqueous sodium bicarbonate, 1 N aqueous HCl, water, brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-78cdcb40abb946b896dcd674e3459d8d
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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