1-Butanol → (R)-6-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitroimidazo[1,2-b]pyridazine

HRID 2096291노트

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HRID 2096291 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=2)[N:7]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[C@H:22]1[CH2:26][CH2:25][CH2:24][NH:23]1.C(O)CCC>CCOC(C)=O>[F:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[C@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=2)[N:7]=1

참가 물질

5

반응물 3

HCID 2631-ButanolHCID 71762902-(2,5-Difluorophenyl)pyrrolidine, (R)-HCID 105359816-Chloro-3-nitro-imidazo(1,2-b)pyridazine

생성물 1

HCID 67307105(R)-6-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitroimidazo[1,2-b]pyridazine수율 75.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
140 °C

실험 절차

A suspension of 6-chloro-3-nitroimidazo[1,2-b]pyridazine (1.0 g, 5.0 mmol) and (R)-2-(2,5-difluorophenyl)pyrrolidine (Prepared as described in Preparation A; 1.9 g, 11 mmol) in n-butanol (4.6 mL, 50 mmol) was sealed in a pressure reaction tube and stirred in a 140° C. oil bath overnight. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc (250 mL), then washed with water (2×150 mL) and brine (150 mL), filtered through a Biotage Phase Separator filter paper and concentrated. The crude material was purified by silica gel chromatography, eluting with 2:1 EtOAc/hexanes to yield the product as a foamy yellow powder (1.3 g, 75% yield).

후처리

  1. customwas sealed in a pressure reaction tube
  2. temperatureAfter cooling to ambient temperature
  3. washwashed with water (2×150 mL) and brine (150 mL)
  4. filtrationfiltered through a Biotage Phase Separator
  5. filtrationfilter paper
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with 2:1 EtOAc/hexanes

출처 및 근거

ORD 기록
ord-d88801aafbd64e9ca594f077bd474ba2
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450322B2

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