Water → HCID 44528613, compound

HRID 1988939Notes

Reaction equation

HRID 1988939 reaction equation
[H-].[Na+].[CH:3]1([NH:6][C:7](=[O:26])[C:8]2[CH:13]=[C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[NH:19][N:18]=[C:17]4[CH3:23])[C:11]([CH3:24])=[C:10]([F:25])[CH:9]=2)[CH2:5][CH2:4]1.[S:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[S:32](Cl)(=[O:34])=[O:33].O>CN(C=O)C.C(Cl)(Cl)Cl>[CH:3]1([NH:6][C:7](=[O:26])[C:8]2[CH:13]=[C:12]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([S:32]([C:28]3[S:27][CH:31]=[CH:30][CH:29]=3)(=[O:34])=[O:33])[N:18]=[C:17]4[CH3:23])[C:11]([CH3:24])=[C:10]([F:25])[CH:9]=2)[CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 855182-Thiophenesulfonyl chlorideHCID 178429755HCID 178429755, compound

Product 1

HCID 44528613HCID 44528613, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% oil dispersion, 0.008 g) was added to a stirred solution of N-cyclopropyl-3-fluoro-4-methyl-5-(3-methyl-1H-indazol-5-yl)benzamide (Example 121) (0.033 g) in dry DMF (1.5 ml) under nitrogen. After 5 min a solution of 2-thiophenesulphonyl chloride (0.038 g) in DMF (0.75 ml) was added and stirring was continued for a further 2 h. Water (1 ml) and chloroform (10 ml) were added, the mixture was passed through a hydrophobic filter and the solvent was evaporated. The residue was purified by preparative Hplc to give the title compound as a clear glass (0.024 g).

Workup

  1. filtrationa hydrophobic filter
  2. customthe solvent was evaporated
  3. customThe residue was purified by preparative Hplc

Sources & evidence

ORD record
ord-c98ab503737e49c48881924f0346815d
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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