Sodium Bicarbonate → ethyl 1-({4-[3-(3-amino-3-thioxopropyl)-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylate

HRID 1257402

Reaction equation

HRID 1257402 reaction equation
[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:15]2[N:16]=[C:17]([CH2:20][N:21]3[CH:25]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:23]=[N:22]3)[S:18][CH:19]=2)[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)#[N:2].P([S-])(OCC)(OCC)=[S:32].C(=O)([O-])O.[Na+]>C(OC(=O)C)C.Cl>[NH2:2][C:1](=[S:32])[CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:15]2[N:16]=[C:17]([CH2:20][N:21]3[CH:25]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:23]=[N:22]3)[S:18][CH:19]=2)[CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 1385274Diethyl dithiophosphate, potassium saltHCID 66939785ethyl 1-({4-[3-(2-cyanoethyl)-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 86650595ethyl 1-({4-[3-(3-amino-3-thioxopropyl)-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylateYield 66%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

To a solution (13 mL) of the compound (2.8 g, 6.5 mmol) obtained in Example 96b in 4N hydrogen chloride ethyl acetate was added O,O-diethyl dithiophosphate (1.8 g, 9.7 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=50/50) to give the title compound (2.0 g, 66%) as a colorless amorphous form.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=50/50)

Sources & evidence

ORD record
ord-b669b89ba2ce4dd689ab35a78c1fa4bb
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Linked notes

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