4-Toluenesulfonyl chloride → HCID 67204679, compound

HRID 1259855Notes

Reaction equation

HRID 1259855 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[C:12]1([C:18]2[CH:27]=[C:26]([C:28]([NH:30][C:31](=S)[NH:32][NH:33][C:34]([C:36]3[S:37][CH:38]=[CH:39][CH:40]=3)=[O:35])=[O:29])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:42][C:43]([F:46])([F:45])[F:44])[CH:24]=3)[N:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[C:12]1([C:18]2[CH:27]=[C:26]([C:28]([NH:30][C:31]3[O:35][C:34]([C:36]4[S:37][CH:38]=[CH:39][CH:40]=4)=[N:33][N:32]=3)=[O:29])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:42][C:43]([F:46])([F:45])[F:44])[CH:24]=3)[N:19]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 86655538HCID 86655538, compound

Product 1

HCID 67204679HCID 67204679, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

p-toluenesulfonyl chloride (32.7 mg, 0.17 mmol) was added to a pyridine (2 mL) solution of 4-(2-phenyl-6-trifluoromethoxy-4-quinolinecarbonyl)-1-(2-thiophenecarbonyl)thiosemicarbazide (70 mg, 0.14 mmol) described in Reference Example 28, and the mixture was stirred overnight at room temperature. The reaction solution was concentrated. After that, to the residue, water was added, and the deposited crystal was collected by filtration, washed with water, dried, and then purified by silica gel column chromatography to obtain the title compound (16 mg, 0.03 mmol).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionAfter that, to the residue, water was added
  3. filtrationthe deposited crystal was collected by filtration
  4. washwashed with water
  5. customdried
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-9cbdc62e5e894fe2bcace851fa7b59d5
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Reaction notes

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