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 1059372노트

반응식

HRID 1059372 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-72d513cf955548f5b6168260afd30beb
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06518423B1

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