Dichloromethane → HCID 86692628, compound

HRID 1748681Notes

Reaction equation

HRID 1748681 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]([CH3:14])[S:10](Cl)(=[O:12])=[O:11].[C:15]([C:17]1([C:23]2[N:28]=[CH:27][C:26]([NH:29][C:30]([C:32]3[CH:33]=[N:34][N:35]([C:38]4[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][N:39]=4)[C:36]=3[CH3:37])=[O:31])=[CH:25][CH:24]=2)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)#[N:16].ClCCl>O>[C:15]([C:17]1([C:23]2[N:28]=[CH:27][C:26]([NH:29][C:30]([C:32]3[CH:33]=[N:34][N:35]([C:38]4[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][N:39]=4)[C:36]=3[CH3:37])=[O:31])=[CH:25][CH:24]=2)[CH2:18][CH2:19][N:20]([S:10](=[O:12])(=[O:11])[N:9]([CH3:14])[CH3:8])[CH2:21][CH2:22]1)#[N:16]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 86692605HCID 86692605, compound

Product 1

HCID 86692628HCID 86692628, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (48 μl) and dimethylsulfamoyl chloride (37 μl) were added to a mixture of N-[6-(4-cyanopiperidin-4-yl)pyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (150 mg) described in Reference Example 169 and dichloromethane (6.6 ml) and stirred at room temperature for two days. Water was added to the reaction solution, extracted with chloroform, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified with silica gel chromatography (chloroform/methanol) to give the titled compound (135 mg) as a white solid.

Workup

  1. extractionextracted with chloroform
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified with silica gel chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-50beb1605b114ccf9fb56fbe36c50dfd
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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