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 628011ノート

反応式

HRID 628011 の反応式
[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

参加物

4

反応物 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

生成物 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

反応条件

温度
90 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-1efbdd3a0a8e4f36b75910b8b05d552e
出典データセット
uspto-grants-2016_04
特許番号
US09309265B2

反応ノート

読み込み中…