1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ethyl [1-[3-[(10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)acetylamino]propyl]piperidin-4-yl]carboxylate

HRID 1059372ノート

反応式

HRID 1059372 の反応式
[N:1]1[C:10]2[NH:9][C:8]3[CH:11]=[C:12]([CH2:15][C:16]([OH:18])=O)[CH:13]=[CH:14][C:7]=3[S:6][C:5]=2[N:4]=[CH:3][CH:2]=1.Cl.Cl.[NH2:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH:28]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:26]1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>O.C(N(CC)CC)C.CN(C)C=O>[CH2:34]([O:33][C:31]([CH:28]1[CH2:27][CH2:26][N:25]([CH2:24][CH2:23][CH2:22][NH:21][C:16](=[O:18])[CH2:15][C:12]2[CH:13]=[CH:14][C:7]3[S:6][C:5]4[N:4]=[CH:3][CH:2]=[N:1][C:10]=4[NH:9][C:8]=3[CH:11]=2)[CH2:30][CH2:29]1)=[O:32])[CH3:35]

参加物

8

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1867013310H-Pyrazino[2,3-b][1,4]benzothiazine-8-acetic acidHCID 18670238Ethyl 1-(3-aminopropyl)piperidine-4-carboxylate dihydrochloride

生成物 1

HCID 23564778Ethyl [1-[3-[(10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)acetylamino]propyl]piperidin-4-yl]carboxylate収率 68.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To 10 ml of N,N-dimethylformamide were added 0.6 g of 10H-pyrazino[2,3-b][1,4]benzothiazine-8-acetic acid, 0.8 g of ethyl 1-(3-aminopropyl)piperidine-4-carboxylate dihydrochloride, 0.38 g of 1-hydroxybenzotriazole, 1.07 ml of triethylamine and 0.53 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and the resulting mixture was stirred at room temperature for 22 hours. After adding water, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and a saturated aqueous solution of sodium. chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol). The crystals thus obtained were washed with ether and thus 0.72 g of the title compound was obtained as a pale brown powder.

後処理

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialchloride, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)
  6. customThe crystals thus obtained
  7. washwere washed with ether

出典と根拠

ORDレコード
ord-72d513cf955548f5b6168260afd30beb
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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