(S)-2-(2-Methoxyethyl)piperazine → (S)-7-Chloro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

HRID 131457

반응식

HRID 131457 반응식
Cl.[Cl:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8]3[S:9][C:10]([CH3:16])=[CH:11][C:12]=3[C:13]([NH2:15])=[N:14][C:5]=2[CH:4]=1.[CH3:19][O:20][CH2:21][CH2:22][C@H:23]1[CH2:28]N[CH2:26][CH2:25][NH:24]1>CS(C)=O.C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[Cl:2][C:3]1[CH:18]=[CH:17][C:6]2[NH:7][C:8]3[S:9][C:10]([CH3:16])=[CH:11][C:12]=3[C:13]([N:15]3[CH2:26][CH2:25][NH:24][C@@H:23]([CH2:22][CH2:21][O:20][CH3:19])[CH2:28]3)=[N:14][C:5]=2[CH:4]=1

참가 물질

6

반응물 2

HCID 55287560(S)-2-(2-Methoxyethyl)piperazineHCID 1363885727-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

생성물 1

HCID 136090361(S)-7-Chloro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene수율 60%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 22340214Dimethylsulfoxide toluene용매

반응 조건

온도
130 °C

실험 절차

Dissolve 7-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride (1.46 g, 4.86 mmol) and (S)-2-(2-methoxy-ethyl)-piperazine (2.1 g, 14.6 mmol) in dimethylsulfoxide/toluene (1:2)(18 ml), stir under nitrogen and heat in an oil bath at 130° C. for 28.5 hours. Stir 16 hours at ambient temperature. Dilute the mixture with water and ethyl acetate, and extract with ethyl acetate. Combine the ethyl acetate extracts, wash with water and brine, dry the organic phase (Na2SO4), filter and concentrate under reduced pressure. Chromatograph on silica gel (eluent: 0-10% 2N ammonia in methanol/dichloromethane) to give the title compound (1.14 g, 60%), Mass Spectrum (ESMS) 391/393 (M+1), mp 179-183° C. (dec).

후처리

  1. stirringStir 16 hours at ambient temperature
  2. extractionextract with ethyl acetate
  3. washwash with water and brine
  4. dry with materialdry the organic phase (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

출처 및 근거

ORD 기록
ord-0de79bc9bdcf4decb9130433baa099b5
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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