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Methanol → N-(5-chloropyridin-2-yl)-3-[2-hydroxy-4-methylthiobenzoylamino]pyridine-2-carboxamide

HRID 1434846
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HRID 1434846 반응식
C([O:4][C:5]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:6]=1[C:7]([NH:9][C:10]1[C:11]([C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=2)=[O:17])=[N:12][CH:13]=[CH:14][CH:15]=1)=[S:8])(=O)C.C1COCC1.CO.C([O-])([O-])=O.[Na+].[Na+]>ClCCl.Cl>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:16]([C:11]2[C:10]([NH:9][C:7](=[S:8])[C:6]3[CH:26]=[CH:27][C:28]([CH3:30])=[CH:29][C:5]=3[OH:4])=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:17])=[N:20][CH:21]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 866200023-[2-acetoxy-4-methylthiobenzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide

생성물 1

HCID 136348818N-(5-chloropyridin-2-yl)-3-[2-hydroxy-4-methylthiobenzoylamino]pyridine-2-carboxamide수율 80.6%

시약·촉매·용매 2

HCID 313
Hydrochloric Acid
용매
HCID 6344Dichloromethane용매

실험 절차

To a mixture of 3-[2-acetoxy-4-methylthiobenzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide (13 g, 28.4 mmol), THF (100 mL) and MeOH (50 mL) was added Na2CO3 (5.75 g, 54.3 mmol), and the mixture was stirred for 18 h. The resulting yellow suspension was diluted with dichloro-methane (100 mL), and 1 N HCl (about 55 mL) was slowly added. The mixture was partitioned and the white organic suspension was concentrated. The residue was triturated with dichloromethane (200 mL) and filtered to give the title compound as a white solid (9.5 g, 22.9 mmol, 80%).

후처리

  1. additionwas slowly added
  2. customThe mixture was partitioned
  3. concentrationthe white organic suspension was concentrated
  4. customThe residue was triturated with dichloromethane (200 mL)
  5. filtrationfiltered

출처 및 근거

ORD 기록
ord-0adebe3d49fa40d6a49218a1497b5fb4
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07615568B2

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