Methanol → 8-bromo-2-[4-(2-chloro-phenyl)-4H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 84594노트

반응식

HRID 84594 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[S:12][C:13]2[CH2:14][CH2:15][O:16][C:17]3[CH:24]=[C:23]([Br:25])[CH:22]=[CH:21][C:18]=3[C:19]=2[N:20]=1)=S.O.[NH2:27][NH2:28].[CH3:29]O>>[Br:25][C:23]1[CH:22]=[CH:21][C:18]2[C:19]3[N:20]=[C:11]([C:9]4[N:8]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[Cl:1])[CH:29]=[N:28][N:27]=4)[S:12][C:13]=3[CH2:14][CH2:15][O:16][C:17]=2[CH:24]=1

참가 물질

4

반응물 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 866348468-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carbothioic acid (2-chloro-phenyl)-amide

생성물 1

HCID 532348928-bromo-2-[4-(2-chloro-phenyl)-4H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

반응 조건

온도
90 °C

실험 절차

A mixture of 8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carbothioic acid (2-chloro-phenyl)-amide (160 mg), methanol (10 mL) and hydrazine hydrate (170 μL) was heated to reflux for 6 hours. The reaction mixture was then cooled and the solid collected by filtration. A mixture of this solid (144 mg) and triethyl orthoformate (5 mL) was heated to 90° C. for 2 hours and then to 130° C. for 2 hours. The reaction mixture was then cooled and the solvent removed in vacuo and the residue purified using flash chromatography to yield 314 (55 mg). NMR: (CDCl3): 3.32 (2H, t), 4.36 (2H, t), 6.96 (1H, dd), 7.11-7.16 (2H, m), 7.49-7.68 (4H, m), 8.30 (1H, s). MS: (ESI+) MH+ 461

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 6 hours
  3. temperatureThe reaction mixture was then cooled
  4. filtrationthe solid collected by filtration
  5. additionA mixture of this solid (144 mg) and triethyl orthoformate (5 mL)
  6. temperatureThe reaction mixture was then cooled
  7. customthe solvent removed in vacuo
  8. customthe residue purified

출처 및 근거

ORD 기록
ord-1a50d371992e433987bcfb6a5fc7ff86
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846762B2

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