Oxalyl chloride → HCID 86655538, compound

HRID 1259871Notes

Reaction equation

HRID 1259871 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([C:13]2[CH:22]=[C:21]([C:23](O)=[O:24])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:26][C:27]([F:30])([F:29])[F:28])[CH:19]=3)[N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[S-:31][C:32]#[N:33].[K+].[S:35]1[CH:39]=[CH:38][CH:37]=[C:36]1[C:40]([NH:42][NH2:43])=[O:41]>CO.C(Cl)Cl>[C:7]1([C:13]2[CH:22]=[C:21]([C:23]([NH:33][C:32](=[S:31])[NH:43][NH:42][C:40]([C:36]3[S:35][CH:39]=[CH:38][CH:37]=3)=[O:41])=[O:24])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:26][C:27]([F:29])([F:28])[F:30])[CH:19]=3)[N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chloride2×HCID 73098Thiophene-2-carbohydrazideHCID 516872Potassium thiocyanateHCID 3912385HCID 3912385, compound

Product 1

HCID 86655538HCID 86655538, compoundYield 46.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (129 μL, 1.50 mmol) and methylene chloride (3 mL) were added to a methylene chloride (2 mL) solution of 2-phenyl-6-trifluoromethoxy-4-quinolinecarboxylic acid (100 mg, 0.30 mmol) described in Reference Example 16, and the mixture was stirred at room temperature for 1 hour. After that, oxalyl chloride (129 μL, 1.50 mmol) was added, and the mixture was further stirred for 2 hours. The reaction solution was concentrated, and the residue was dissolved in anhydrous acetonitrile (1 mL). To the solution, potassium thiocyanate (146 mg, 1.50 mmol) was added, and the mixture was stirred at room temperature for 1 hour. To the reaction solution, commercially available 2-thiophenecarbohydrazide (64 mg, 0.45 mmol) was added, and the mixture was stirred overnight at room temperature. To the reaction solution, methanol was added, and the mixture was concentrated. To the residue, a saturated aqueous solution of sodium chloride 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 (71 mg, 0.14 mmol).

Workup

  1. stirringthe mixture was further stirred for 2 hours
  2. concentrationThe reaction solution was concentrated
  3. dissolutionthe residue was dissolved in anhydrous acetonitrile (1 mL)
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. stirringthe mixture was stirred overnight at room temperature
  6. concentrationthe mixture was concentrated
  7. additionTo the residue, a saturated aqueous solution of sodium chloride was added
  8. filtrationthe deposited crystal was collected by filtration
  9. washwashed with water
  10. customdried
  11. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-dd7004a45e584c8ca9f92c7d1a9cf978
Source dataset
uspto-grants-2013_06
Patent number
US08466290B2

Reaction notes

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