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

반응식

HRID 1190271 반응식
[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

참가 물질

4

반응물 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

생성물 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]azulene수율 40.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
160 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-52af37fe387e43d8b700a673a037423d
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673952B2

연결된 노트

불러오는 중…