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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Cesium carbonate → N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-4-pyrimidinyl]azetidine-1-sulphonamide

HRID 1024837
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HRID 1024837 반응식
Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH:9]2[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]2)[N:5]=[C:4]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=2[F:26])[N:3]=1.[N:27]1([S:31]([NH2:34])(=[O:33])=[O:32])[CH2:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:26][C:20]1[C:21]([F:25])=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][S:17][C:4]1[N:3]=[C:2]([NH:34][S:31]([N:27]2[CH2:30][CH2:29][CH2:28]2)(=[O:33])=[O:32])[CH:7]=[C:6]([CH2:8][CH:9]2[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]2)[N:5]=1
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 450805661-AzetidinesulfonamideHCID 866198634-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]pyrimidine

생성물 1

HCID 53628340N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-4-pyrimidinyl]azetidine-1-sulphonamide

시약·촉매·용매 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 312751,4-Dioxane용매

실험 절차

A solution of the product of step i) (109 mg), tris(dibenzylideneacetone)dipalladium(0) (14 mg), azetidine-1-sulphonamide (145 mg), 2-dicyclohexyl-phosphino-2′,4′,6′-triisopropyl,1,1′-biphenyl (XPHOS) (14 mg) and cesium carbonate (120 mg) in anhydrous dioxane (2.3 ml) was heated at 100° C. for 45 min. The reaction mixture was partitioned between ethyl acetate and water. Acetic acid (0.2 ml) was added and the separated organic phase was washed with water and brine, dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash silica-gel chromatography eluting with 40% ethyl acetate in iso-hexane to give the sub-title compound as a yellow viscous oil. Yield: 78 mg.

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. additionAcetic acid (0.2 ml) was added
  3. washthe separated organic phase was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was purified by flash silica-gel chromatography
  7. washeluting with 40% ethyl acetate in iso-hexane

출처 및 근거

ORD 기록
ord-6f39fa6155c6460889645e437c81ebb2
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722883B2

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