Cesium carbonate → HCID 58012174、化合物

HRID 660946ノート

反応式

HRID 660946 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11](=[O:13])[N:10]([CH2:14][C:15]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])=[O:16])[N:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:36][CH2:37][Cl:38]>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.C(OCC)(=O)C>[Cl:38][CH2:37][CH2:36][N:12]1[C:11](=[O:13])[N:10]([CH2:14][C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([F:26])([F:27])[F:28])=[O:16])[N:9]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

参加物

8

反応物 3

HCID 10796Cesium carbonateHCID 1364381-Chloro-2-iodoethaneHCID 1361991092-[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[2-(tri-fluoromethyl)benzyl]-acetamide

生成物 1

HCID 58012174HCID 58012174、化合物

試薬・触媒・溶媒 4

HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

500 mg (1.01 mmol) of 2-[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[2-(trifluoromethyl)benzyl]-acetamide from Example 243A are dissolved in 10 ml of toluene with 230 mg (1.01 mmol) of benzyltriethylammonium chloride. Next, a solution of 658 mg (2.02 mmol) of caesium carbonate, dissolved in 1.0 ml water, is added, and the mixture vigorously stirred at RT for 30 mins. After addition of 1.92 g (10.13 mmol) of 1-iodo-2-chloroethane, the mixture is heated for 7 hrs at 80° C. with vigorous stirring. The suspension is then diluted with ethyl acetate and washed once each with water, 10% sodium thiosulphate and saturated ammonium chloride solution. The organic phase is dried over sodium sulphate, filtered and concentrated in vacuo. The crude product is purified by preparative HPLC [Method 9]. 195 mg (41% of theory) of the target compound are thus obtained.

後処理

  1. additionis added
  2. temperaturethe mixture is heated for 7 hrs at 80° C. with vigorous stirring
  3. washwashed once each with water, 10% sodium thiosulphate and saturated ammonium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by preparative HPLC [Method 9]
  8. custom195 mg (41% of theory) of the target compound are thus obtained

出典と根拠

ORDレコード
ord-58b966efd83d47ffb5ab1a4a392881fc
出典データセット
uspto-grants-2011_12
特許番号
US08084481B2

反応ノート

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