2-Propanamine, hydrochloride (1:1) → 8-Bromo-2-(4-isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 1190271

反応式

HRID 1190271 の反応式
[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]3[N:7]=[C:8]([C:14]4O[CH:16]=[N:17][N:18]=4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.Cl.[CH:22]([NH2:25])([CH3:24])[CH3:23]>N1C=CC=CC=1>[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]3[N:7]=[C:8]([C:14]4[N:25]([CH:22]([CH3:24])[CH3:23])[CH:16]=[N:17][N:18]=4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 64321372-Propanamine, hydrochloride (1:1)HCID 579001858-Bromo-2-[1,3,4]oxadiazol-2-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

生成物 1

HCID 582038068-Bromo-2-(4-isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene収率 40.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
160 °C

実験手順

To a solution of 8-bromo-2-[1,3,4]oxadiazol-2-yl-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene (4.38 g, 12.51 mmol) in pyridine (12 mL) was added isopropylamine hydrochloride (1.38 g, 12.51 mmol). The reaction mixture was heated at 160° C. for 30 minutes using microwave irradiation before being concentrated in vacuo. The residue was taken up into DCM then washed with 1M HCl then brine before being dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by flash chromatography (SiO2, gradient 0-3% methanol in DCM then further purified, gradient 0-4% MeOH in EtOAc) to yield the title compound as an orange solid (1.97 g, 40%). LCMS: RT=4.67 min, M+H+=391/393.

後処理

  1. custommicrowave irradiation
  2. concentrationbefore being concentrated in vacuo
  3. washthen washed with 1M HCl
  4. dry with materialbrine before being dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by flash chromatography (SiO2, gradient 0-3% methanol in DCM
  7. customthen further purified

出典と根拠

ORDレコード
ord-52af37fe387e43d8b700a673a037423d
出典データセット
uspto-grants-2014_03
特許番号
US08673952B2

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