Sodium Chloride → N-[3-(1-aminoethyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide

HRID 1500066ノート

反応式

HRID 1500066 の反応式
[C:1]([BH3-])#[N:2].[Na+].[C:5]([C:8]1[CH:9]=[C:10]([NH:15][C:16]([C:18]2N(C)[N:21]=[C:20]([C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])[C:19]=2[C:31]([F:34])([F:33])[F:32])=[O:17])[CH:11]=[CH:12][C:13]=1[Cl:14])(=O)[CH3:6].C([O-])(=O)C.[NH4+:39].[Cl-].[Na+]>CO>[NH2:39][CH:5]([C:8]1[CH:9]=[C:10]([NH:15][C:16]([C:18]2[N:2]([CH3:1])[N:21]=[C:20]([C:24]([F:30])([F:29])[C:25]([F:28])([F:26])[F:27])[C:19]=2[C:31]([F:32])([F:34])[F:33])=[O:17])[CH:11]=[CH:12][C:13]=1[Cl:14])[CH3:6]

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 89650518N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide

生成物 1

HCID 89650757N-[3-(1-aminoethyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide収率 46.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium cyanoborohydride (163 mg, 2.59 mmol, 3.0 eq.) was added to a solution of N-(3-acetyl-4-chlorophenyl)-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (400 mg, 0.863 mmol) and ammonium acetate (1.33 g, 17.3 mmol, 20 eq.) in methanol (15 ml). The mixture was stirred at room temperature for 4 h and then heated to 80° C. and kept at this temperature for 3 h. The mixture was cooled to room temperature and left overnight. Sat. aq. sodium chloride solution was added, the mixture was extracted with ethyl acetate and the extract was washed with sat. aq. sodium chloride solution and dried over MgSO4. After concentration under reduced pressure, the product was purified by column chromatography (hexane/ethyl acetate) to give N-[3-(1-aminoethyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (186 mg, 46%).

後処理

  1. temperatureheated to 80° C.
  2. waitkept at this temperature for 3 h
  3. temperatureThe mixture was cooled to room temperature
  4. waitleft overnight
  5. extractionthe mixture was extracted with ethyl acetate
  6. washthe extract was washed with sat. aq. sodium chloride solution
  7. dry with materialdried over MgSO4
  8. concentrationAfter concentration under reduced pressure
  9. customthe product was purified by column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-200b94699b944e538ba242e2d224e45b
出典データセット
uspto-grants-2015_12
特許番号
US09204645B2

反応ノート

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