Imidazole → 5-(Isoquinolin-6-yl)-1,3,4-oxadiazol-2-amine

HRID 598813노트

반응식

HRID 598813 반응식
Br[C:2]#[N:3].N1C=CN=C1.[CH:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]([NH:21][NH2:22])=[O:20])=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1>C(Cl)Cl.C1COCC1>[CH:9]1[C:18]2[C:13](=[CH:14][C:15]([C:19]3[O:20][C:2]([NH2:3])=[N:22][N:21]=3)=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 10476Cyanogen BromideHCID 57950576Isoquinoline-6-carbohydrazide

생성물 1

HCID 579507005-(Isoquinolin-6-yl)-1,3,4-oxadiazol-2-amine수율 96%

시약·촉매·용매 2

HCID 6344Dichloromethane용매3회HCID 8028Tetrahydrofuran용매

실험 절차

A 3 M DCM solution of bromoformonitrile (0.2 mL, 0.6 mmol) (commercially available from Aldrich) was mixed with imidazole (0.157 g, 2.3 mmol) (commercially available from Aldrich) in 10 mL DCM. The mixture was heated and maintained to reflux for 30 minutes in a round bottom flask. After the DCM was removed under a reduced pressure, isoquinoline-6-carbohydrazide (0.1 g, 0.53 mmol) suspended in 50 mL THF was added into the flask. The mixture was heated and maintained at reflux for 3 hours. After removing the THF, the remaining residue was mixed with 10 mL water and filtered. After washing with water and air drying, a white solid was obtained as the desired product (0.107 g, 96%) LCMS (API-ES) m/z (%): 213.0 (100%, M++H).

후처리

  1. temperatureThe mixture was heated
  2. temperaturemaintained
  3. temperatureto reflux for 30 minutes in a round bottom flask
  4. additionwas added into the flask
  5. temperatureThe mixture was heated
  6. temperaturemaintained
  7. temperatureat reflux for 3 hours
  8. customAfter removing the THF
  9. additionthe remaining residue was mixed with 10 mL water
  10. filtrationfiltered
  11. washAfter washing with water and air
  12. customdrying

출처 및 근거

ORD 기록
ord-53307459c2174ae4abcfce777831b6e5
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897619B2

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