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

HRID 1434846
Notes
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Reaction equation

HRID 1434846 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

2
HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-0adebe3d49fa40d6a49218a1497b5fb4
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07615568B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes