Triethylamine → 2-tert-Butyl-5-pyridin-2-yl-2H-pyrazol-3-ylamine

HRID 1260317노트

반응식

HRID 1260317 반응식
O=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH2:3][C:4]#[N:5].C(N(CC)CC)C.Cl.[C:20]([NH:24][NH2:25])([CH3:23])([CH3:22])[CH3:21]>CCO.CCOC(C)=O>[C:20]([N:24]1[C:4]([NH2:5])=[CH:3][C:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[N:25]1)([CH3:23])([CH3:22])[CH3:21]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 81889tert-Butylhydrazine monohydrochlorideHCID 115718233-Oxo-3-(pyridin-2-yl)propanenitrile

생성물 1

HCID 672999182-tert-Butyl-5-pyridin-2-yl-2H-pyrazol-3-ylamine수율 62.7%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 3-oxo-3-pyridin-2-yl-propionitrile (0.40 g, 2.7 mmol; CAS 54123-21-6) at r.t. in EtOH (10 ml) under an argon atmosphere were added triethylamine (1.1 ml, 8.2 mmol) and t-butylhydrazine hydrochloride (1.02 g, 8.2 mmol). The mixture was heated to reflux and stirring was continued for 2 hrs. The orange solution was cooled to r.t. The solids were filtered off. The filtrate was concentrated to leave an orange viscous oil which was taken up in EtOAc and washed with water. The aqueous layer was extracted with EtOAc and with CH2Cl2/MeOH 9:1. The combined organics were dried over MgSO4, filtered and concentrated. After silica gel chromatography using CH2Cl2/MeOH as gradient, the product was obtained as off-white solid (0.366 g, 62%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationThe solids were filtered off
  4. concentrationThe filtrate was concentrated
  5. customto leave an orange viscous oil which
  6. washwashed with water
  7. extractionThe aqueous layer was extracted with EtOAc and with CH2Cl2/MeOH 9:1
  8. dry with materialThe combined organics were dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-acda246a8d9440a295ec7f6d081b381e
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470820B2

반응 노트

불러오는 중…