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

反応式

HRID 1257402 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21866389Hydrogen chloride-ethyl acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b669b89ba2ce4dd689ab35a78c1fa4bb
出典データセット
uspto-grants-2013_06
特許番号
US08461348B2

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