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

HRID 1059370ノート

反応式

HRID 1059370 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ed445e65dc544faf96eefe21a7be4870
出典データセット
uspto-grants-2003_02
特許番号
US06518423B1

反応ノート

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