Cyclopropyl-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-methanone → Cyclopropyl-(2-methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-methanone

HRID 133540

반응식

HRID 133540 반응식
[CH:1]1([C:4]([C:6]2[C:7]([CH3:25])=[N:8][C:9]3[S:10][C:11]4[CH2:12][NH:13][CH2:14][CH2:15][C:16]=4[C:17]=3[C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:5])[CH2:3][CH2:2]1>C1(C=CC2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH:1]1([C:4]([C:6]2[C:7]([CH3:25])=[N:8][C:9]3[S:10][C:11]4[C:16]([C:17]=3[C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=[N:13][CH:12]=4)=[O:5])[CH2:2][CH2:3]1

참가 물질

4

반응물 1

HCID 68896615Cyclopropyl-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-methanone

생성물 1

HCID 11508442Cyclopropyl-(2-methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-methanone수율 8%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 11502Stilbene용매

반응 조건

온도
150 °C

실험 절차

To a stirred solution of 0.46 g (1.32 mmol) cyclopropyl-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-methanone in 7 ml diphenylethylene was added 230 mg palladium on charcoal 10%. The mixture was stirred over night at 150° C., and then poured onto ethyl acetate (about 150 ml), and extracted three times aqueous HCl (1M). The combined aqueous phases were basified with K2CO3 until ph=8, and then the product was extracted with ethyl acetate. The combined organic phase were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 1:1) afforded 35 mg (8%) cyclopropyl-(2-methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-methanone as a light yellow solid. ES-MS m/e (%): 345 (M+H+, 100).

후처리

  1. additionpoured onto ethyl acetate (about 150 ml)
  2. extractionextracted three times aqueous HCl (1M)
  3. extractionthe product was extracted with ethyl acetate
  4. dry with materialThe combined organic phase were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-aa59d649f886481b9711f5c1699912e0
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390903B2

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