Potassium Carbonate → HCID 73438563, compound

HRID 1470787Notes

Reaction equation

HRID 1470787 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[C:23]([CH3:24])=[CH:22][C:21]([Cl:25])=[CH:20][C:9]=1[C:10]([N:12]=[S:13]([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])=[O:11].[Cl:26][C:27]1[C:28]([N:33]2[C:37]([C:38](Cl)=[O:39])=[CH:36][C:35]([C:41]([F:44])([F:43])[F:42])=[N:34]2)=[N:29][CH:30]=[CH:31][CH:32]=1>C1(C)C=CC=CC=1.CCOC(C)=O.O>[Cl:26][C:27]1[C:28]([N:33]2[C:37]([C:38]([NH:7][C:8]3[C:9]([C:10](=[O:11])[N:12]=[S:13]([CH:17]([CH3:18])[CH3:19])[CH:14]([CH3:16])[CH3:15])=[CH:20][C:21]([Cl:25])=[CH:22][C:23]=3[CH3:24])=[O:39])=[CH:36][C:35]([C:41]([F:44])([F:42])[F:43])=[N:34]2)=[N:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 184469281-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl ChlorideHCID 86720674HCID 86720674, compound

Product 1

HCID 73438563HCID 73438563, compoundYield 68.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of potassium carbonate (9.73 g, 70.0 mmol, 1.10 equiv) and 2-amino-5-chloro-N-(diisopropyl-λ4-sulfanylidene)-3-methyl-benzamide (18.7 g, 62.4 mmol, 1.00 equiv) in toluene (80 mL) a solution of 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carbonyl chloride (20.1 g, 64.1 mmol, 1.03 equiv.) in toluene (40 mL) was added at 60° C. After 35 minutes at 60° C., the reaction mixture was cooled to room temperature and diluted with EtOAc (50 mL) and water (50 mL). The organic phase was washed with water (50 mL), 0.1 M HCl (50 mL), dried over Na2SO4 and concentrated. The crude product was recrystallized from methyl tert-butyl ether to yield the title compound (24.4 g, 66%). The crystalline material was analyzed by means of DSC and by means of X-ray powder diffractometry (XRPD). The data revealed that form I of Va-2 was obtained.

Workup

  1. additionwas added at 60° C
  2. washThe organic phase was washed with water (50 mL), 0.1 M HCl (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was recrystallized from methyl tert-butyl ether

Sources & evidence

ORD record
ord-73fa6f1b7b404d08b4fcd8f67203fc79
Source dataset
uspto-grants-2015_04
Patent number
US09006485B2

Reaction notes

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