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3,6-Dichloropyridazine → Methyl(3S,4R)-4-(2,4-difluorophenyl)-1-(6-chloropyridazin-3-yl)pyrrolidine-3-carboxylate

HRID 1666011
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HRID 1666011 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:13][NH:12][CH2:11][C@H:10]1[C:14]([O:16][CH3:17])=[O:15].CCN(C(C)C)C(C)C.[Cl:27][C:28]1[N:29]=[N:30][C:31](Cl)=[CH:32][CH:33]=1>O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]1[CH2:13][N:12]([C:31]2[N:30]=[N:29][C:28]([Cl:27])=[CH:33][CH:32]=2)[CH2:11][C@H:10]1[C:14]([O:16][CH3:17])=[O:15]
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참가 물질

5

반응물 3

HCID 673313,6-DichloropyridazineHCID 81531DiisopropylethylamineHCID 59130986methyl (3S,4R)-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate2회

생성물 1

HCID 59808482Methyl(3S,4R)-4-(2,4-difluorophenyl)-1-(6-chloropyridazin-3-yl)pyrrolidine-3-carboxylate수율 65%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

The product of Step A, methyl (3S,4R)-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate (0.46 g, 1.91 mmol) was dissolved in dioxane (2 ml). DIPEA (1.33 mL, 7.64 mmol) and 3,6-dichloropyridazine (1.42 g, 9.55 mmol) were added. The reaction was conducted at 120° C. for 5 minutes and at 150° C. for 10 minutes with microwave. Then, the reaction mixture was concentrated in vacuo. The obtained residue was diluted with EtOAc, washed with water and purified by column chromatography (eluent: EtOAc/Hex=1/5) to give the title compound (0.44 g, 65%).

후처리

  1. concentrationThen, the reaction mixture was concentrated in vacuo
  2. additionThe obtained residue was diluted with EtOAc
  3. washwashed with water
  4. custompurified by column chromatography (eluent: EtOAc/Hex=1/5)

출처 및 근거

ORD 기록
ord-26e0a307ad2d4b969284ba233c073570
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08039622B2

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