2,2,2-Trifluoroethanesulfonyl chloride → 2,2,2-trifluoro-ethanesulfonic acid (6-{(E)-2-[3-tert-butyl-5-(5-fluoro-2-methoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-pyridin-3-yl)-amide

HRID 2390867노트

반응식

HRID 2390867 반응식
[C:1]([C:5]1[C:6]([O:29][CH3:30])=[C:7](/[CH:20]=[CH:21]/[C:22]2[N:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:18][CH3:19])=[N:13][CH:14]=[C:15]([F:17])[CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[F:31][C:32]([F:39])([F:38])[CH2:33][S:34](Cl)(=[O:36])=[O:35]>N1C=CC=CC=1>[C:1]([C:5]1[C:6]([O:29][CH3:30])=[C:7](/[CH:20]=[CH:21]/[C:22]2[N:27]=[CH:26][C:25]([NH:28][S:34]([CH2:33][C:32]([F:39])([F:38])[F:31])(=[O:36])=[O:35])=[CH:24][CH:23]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:18][CH3:19])=[N:13][CH:14]=[C:15]([F:17])[CH:16]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 672865546-{(E)-2-[3-tert-butyl-5-(5-fluoro-2-methoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-pyridin-3-ylamine

생성물 1

HCID 672872432,2,2-trifluoro-ethanesulfonic acid (6-{(E)-2-[3-tert-butyl-5-(5-fluoro-2-methoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-pyridin-3-yl)-amide수율 72%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

step 2—To a solution of 370 (90.0 mg, 0.221 mmol) in pyridine (3 mL) cooled to 0° C. was added 2,2,2 trifluoroethane sulfonyl chloride (40 μL, 0.364 mmol). After 20 min the reaction mixture was warmed to RT and stirred overnight. The reaction mixture was quenched with 30 mL of 1N HCl and thrice extracted with EtOAc (20 mL). The combined extracts were washed with sat'd. aq. CuSO4 (3×30 mL) and brine, dried (Na2SO4), filtered, and concentrated. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (25 to 35% EtOAc) to afford 88.1 mg (72%) of 2,2,2-trifluoro-ethanesulfonic acid (6-{(E)-2-[3-tert-butyl-5-(5-fluoro-2-methoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-pyridin-3-yl)-amide (372).

후처리

  1. customThe reaction mixture was quenched with 30 mL of 1N HCl and thrice
  2. extractionextracted with EtOAc (20 mL)
  3. washThe combined extracts were washed with sat'd
  4. dry with materialaq. CuSO4 (3×30 mL) and brine, dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with an EtOAc/hexane gradient (25 to 35% EtOAc)

출처 및 근거

ORD 기록
ord-47d89bf8e02949f4929d63b9a213bcd5
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273773B2

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