Cesium carbonate → HCID 58012174, 화합물

HRID 660946노트

반응식

HRID 660946 반응식
[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

참가 물질

8

반응물 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

생성물 1

HCID 58012174HCID 58012174, 화합물

시약·촉매·용매 4

HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-58b966efd83d47ffb5ab1a4a392881fc
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084481B2

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