3-Fluorophenyl isothiocyanate → (4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-(3-fluoro-phenyl)-amine

HRID 532584

반응식

HRID 532584 반응식
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=O)[CH2:7][CH2:8][C:2]1=2.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N:17]=[C:18]=S)[CH:12]=1.C[Si](C)(C)[Si](C)(C)C.[Li].O.[NH2:30][NH2:31]>C1COCC1.O.C(O)(=O)C>[S:1]1[CH:5]=[CH:4][C:3]2[C:6]3[NH:30][N:31]=[C:18]([NH:17][C:13]4[CH:14]=[CH:15][CH:16]=[C:11]([F:10])[CH:12]=4)[C:7]=3[CH2:8][C:2]1=2

참가 물질

8

반응물 4

HCID 98343-Fluorophenyl isothiocyanateHCID 24654Hydrazine hydrate (1:1)HCID 19586324H,5H,6H-cyclopenta[b]thiophen-4-oneHCID 57425481Lithium hexamethyldisilane

생성물 1

HCID 18445685(4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-(3-fluoro-phenyl)-amine수율 33%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 5,6-Dihydro-cyclopenta[b]thiophen-4-one (1.0 g, 7.4 mmol) and 1-Fluoro-3-isothiocyanato-benzene (1.5 g, 7.2 mmol) in THF (2.0 mL) was added to lithium hexamethyl disilane (7.0 mL, 7.2 mmol) dropwise at room temperature. The reaction mixture was stirred for 8 hr. Hydrazine monohydrate (0.4 mL, 7.9 mmol) and glacial acetic acid (0.5 mL) were added to the reaction mixture, which was then heated at the reflux temperature for 24 hr. The resulting mixture was added to water (30 mL) and then extracted with ethyl acetate. The target product was purified by gravity column chromatography (50% EtOAc in hexane) to give (4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-(3-fluoro-phenyl)-amine as brown solid in 33% yield.

후처리

  1. temperaturewas then heated at the reflux temperature for 24 hr
  2. extractionextracted with ethyl acetate
  3. customThe target product was purified by gravity column chromatography (50% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-d5063d8b3f4649ba83a7d45eb9813672
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853207B2

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