Hydrochloric Acid → 2-Cyclopropylamino-6-(methanesulfonyl-methylamino)-isonicotinic acid

HRID 732443Notes

Reaction equation

HRID 732443 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([N:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH3:11])[N:7]=[C:6]([NH:16][CH:17]2[CH2:19][CH2:18]2)[CH:5]=1.[OH-].[Na+].Cl>CO>[CH:17]1([NH:16][C:6]2[CH:5]=[C:4]([CH:9]=[C:8]([N:10]([S:12]([CH3:15])(=[O:13])=[O:14])[CH3:11])[N:7]=2)[C:3]([OH:20])=[O:2])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 688183812-Cyclopropylamino-6-(methanesulfonyl-methylamino)-isonicotinic acid methylester

Product 1

HCID 688145452-Cyclopropylamino-6-(methanesulfonyl-methylamino)-isonicotinic acidYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Treat a solution of 2-cyclopropylamino-6-(methanesulfonyl-methylamino)-isonicotinic acid methyl ester (261 mg, 0.87 mmol) in methanol (8 mL) with 1 N NaOH (1.3 mL, 1.31 mmol) at room temperature. Stir for 5 h, acidify with 1 N HCl to about pH=3. Extract the reaction mixture with ethyl acetate, dry (sodium sulfate) and concentrate to give the title compound (226 mg, 91%).

Workup

  1. extractionExtract the reaction mixture with ethyl acetate
  2. dry with materialdry (sodium sulfate)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-4ada9f5107f5473f81b961757d309c23
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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