Water → Ethyl [3-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)-3-azabicyclo[3.1.0]hex-6-yl]carboxylate

HRID 1059370노트

반응식

HRID 1059370 반응식
[CH2:1]([O:3][C:4]([CH:6]1[CH:11]2[CH:7]1[CH2:8][NH:9][CH2:10]2)=[O:5])[CH3:2].C(=O)([O-])O.[Na+].Cl[CH2:18][C:19]1[CH:20]=[CH:21][C:22]2[S:27][C:26]3[N:28]=[CH:29][CH:30]=[N:31][C:25]=3[NH:24][C:23]=2[CH:32]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH:11]2[CH:7]1[CH2:8][N:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]3[S:27][C:26]4[N:28]=[CH:29][CH:30]=[N:31][C:25]=4[NH:24][C:23]=3[CH:32]=1)[CH2:10]2)=[O:5])[CH3:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 35222743-Azabicyclo(3.1.0)hexane-6-carboxylic acid, ethyl esterHCID 117470388-Chloromethyl-10H-pyrazino[2,3-b][1,4]benzothiazine

생성물 1

HCID 23564762Ethyl [3-(10H-pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl)-3-azabicyclo[3.1.0]hex-6-yl]carboxylate수율 28%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution of 1.523 g of ethyl(3-azabicyclo[3.1.0]hex-6-yl)carboxylate in N,N-dimethylformamide (30 ml) were added 2.30 g of sodium hydrogencarbonate and 1.39 g of 8-chloromethyl-10H-pyrazino[2,3-b][1,4]benzothiazine and the resulting mixture was heated to 80° C. for 2 hours. After adding water and ethyl acetate, the organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. Then the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.574 g of the title compound as pale yellow crystals.

후처리

  1. washthe organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThen the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-ed445e65dc544faf96eefe21a7be4870
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06518423B1

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