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Methanesulfonyl chloride → N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamide

HRID 2390839
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HRID 2390839 반응식
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([N:8]([C:10]2[CH:15]=[C:14]([C:16]3[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:13]=[C:12]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:11]=2[O:28][CH3:29])[CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>N1C=CC=CC=1.CCOC(C)=O>[C:24]([C:12]1[C:11]([O:28][CH3:29])=[C:10]([N:8]([CH3:9])[C:6](=[O:7])[C:5]2[CH:30]=[CH:31][C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])=[CH:3][CH:4]=2)[CH:15]=[C:14]([C:16]2[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:13]=1)([CH3:25])([CH3:26])[CH3:27]
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참가 물질

5

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 672926244-amino-N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-N-methylbenzamide

생성물 1

HCID 67070141N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamide수율 97%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857
Ethyl Acetate
용매

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온도
0 °C

실험 절차

step 3—To a solution of 140 (0.15 g, 0.36 mmol) in pyridine (3 mL) cooled to 0° C. was added methanesulfonyl chloride (0.053 g, 0.46 mmol) and the resulting solution stirred at 0° C. for 2 h, followed by 2 h at RT. The reaction mixture was diluted with EtOAc, washed sequentially with aqueous CuSO4 and 2N HCl, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient to afford 0.17 g (97%) of N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamide (142) as a white foam (0.17 g, 94%

후처리

  1. waitfollowed by 2 h at RT
  2. washwashed sequentially with aqueous CuSO4 and 2N HCl
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by SiO2 chromatography
  7. washeluting with an EtOAc/hexane gradient

출처 및 근거

ORD 기록
ord-67ec89a0183148e6be83f0d73097f29d
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08273773B2

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