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

반응식

HRID 1257402 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 21866389Hydrogen chloride-ethyl acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b669b89ba2ce4dd689ab35a78c1fa4bb
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461348B2

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