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Hydrogen Bromide → N-[3-tert-butyl-2-methoxy-5-(2-oxo-1,2-dihydropyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamide

HRID 2390840
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인쇄 미리보기

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HRID 2390840 반응식
[C:1]([C:5]1[C:6]([O:34][CH3:35])=[C:7]([N:19]([CH3:33])[C:20](=[O:32])[C:21]2[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][CH:22]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:17]C)=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br>CC(O)=O.CCOC(C)=O>[C:1]([C:5]1[C:6]([O:34][CH3:35])=[C:7]([N:19]([CH3:33])[C:20](=[O:32])[C:21]2[CH:22]=[CH:23][C:24]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])=[CH:25][CH:26]=2)[CH:8]=[C:9]([C:11]2[C:12](=[O:17])[NH:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 2

HCID 260Hydrogen BromideHCID 67070141N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamide

생성물 1

HCID 67069871N-[3-tert-butyl-2-methoxy-5-(2-oxo-1,2-dihydropyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamide수율 94%

시약·촉매·용매 2

HCID 176Acetic Acid용매
HCID 8857
Ethyl Acetate
용매

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온도
60 °C

실험 절차

To a solution of 142 (0.17 g, 0.33 mmol) in HOAc (3 mL) was added concentrated aqueous HBr (48%, 0.11 mL), and the solution was heated in a sealed tube at 60° C. for 15 h. The reaction mixture was cooled to RT, diluted with EtOAc, and washed sequentially with water and saturated aqueous NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with DCM/MeOH/NH4OH to afford 0.15 g (93%) of N-[3-tert-butyl-2-methoxy-5-(2-oxo-1,2-dihydropyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamide (I-104) as a white powder.

후처리

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed sequentially with water and saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by SiO2 chromatography
  7. washeluting with DCM/MeOH/NH4OH

출처 및 근거

ORD 기록
ord-5143f2b5d6a14833ad42d72953d7ad0b
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08273773B2

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