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 707812

반응식

HRID 707812 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-9a02caaf6eb746ba91e68f43aff45e1a
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09175009B2

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