Water → 2-amino-5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carbonitrile

HRID 610045노트

반응식

HRID 610045 반응식
[C:1]([CH2:3][C:4]([NH2:6])=[NH:5])#[N:2].Cl.C(CC(=N)OCC)#N.Br[CH:17]([CH3:27])[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[F:26])=O.O>C(O)C>[NH2:5][C:4]1[NH:6][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])=[C:17]([CH3:27])[C:3]=1[C:1]#[N:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 12342543Ethyl 2-cyanoacetimidate hydrochlorideHCID 220564242-CyanoacetimidamideHCID 221113342-Bromo-1-(2-fluorophenyl)propan-1-one

생성물 1

HCID 101767492-amino-5-(2-fluorophenyl)-4-methyl-1H-pyrrole-3-carbonitrile

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To an ethanolic solution of 2-cyanoacetamidine prepared from 10 g of ethyl 2-cyanoacetimidate hydrochloride as in Reference Example 2 was added a solution of 2-bromo-2'- fluoropropiophenone (7.6 g) in ethanol dropwise under ice-cooling with stirring, and the mixture was then stirred at room temperature overnight. This reaction mixture was poured into iced water (500 g) and the resulting crystals were collected by filtration. The crude crystal crop was washed well with n-hexane, air-dried, and purified by flash chromatography (Kieselgel 60H, 90 g; eluent: 30% ethyl acetate/n-hexane). Recrystallization from benzene-n-hexane (1:1) yielded the title compound as colorless crystals (4.67 g). the physical constants of this product were in agreement with those of the product obtained in Example 5-(1).

후처리

  1. temperaturecooling
  2. stirringthe mixture was then stirred at room temperature overnight
  3. filtrationthe resulting crystals were collected by filtration
  4. washThe crude crystal crop was washed well with n-hexane
  5. customair-dried
  6. custompurified by flash chromatography (Kieselgel 60H, 90 g; eluent: 30% ethyl acetate/n-hexane)
  7. customRecrystallization from benzene-n-hexane (1:1)

출처 및 근거

ORD 기록
ord-f3916edcc9ed4fd1879ba938e3fe64bb
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998459

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