Amoxapine → (E)-ethyl 2-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)pyrimidine-5-carboxylate

HRID 1946591

반응식

HRID 1946591 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=[C:7]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:6]=2[CH:22]=1.CS([C:27]1[N:32]=[CH:31][C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][N:28]=1)(=O)=O>COCCOC.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=[C:7]([N:16]3[CH2:21][CH2:20][N:19]([C:27]4[N:28]=[CH:29][C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:31][N:32]=4)[CH2:18][CH2:17]3)[C:6]=2[CH:22]=1

참가 물질

5

반응물 2

HCID 2170AmoxapineHCID 254889Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate

생성물 1

HCID 59783732(E)-ethyl 2-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)pyrimidine-5-carboxylate수율 100.2%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of (E)-2-chloro-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepine (0.25 g, 0.8 mmol) and ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate (0.13 g, 0.57 mmol) in DME was stirred at room temperature for 1 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with saturated aqueous solution of bicarbonate, water, acetic acid and sodium acetate (pH=4), dried over sodium sulfate and solvent evaporated. The resulting crude residue was purified by flash chromatography (0% to 30% ethyl acetate in hexane) to afford title compound 116 (0.265 g, quant.).

후처리

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous solution of bicarbonate, water, acetic acid and sodium acetate (pH=4)
  4. dry with materialdried over sodium sulfate and solvent
  5. customevaporated
  6. customThe resulting crude residue was purified by flash chromatography (0% to 30% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-a6f259a7f0b64a8fb072acb43ad196b1
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399452B2

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