Hydrochloric Acid → HCID 68814989, compound

HRID 732464Notes

Reaction equation

HRID 732464 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])[N:7]=[C:6]([N:15]([S:17]([CH3:20])(=[O:19])=[O:18])[CH3:16])[CH:5]=1.[OH-].[Li+].Cl>C1COCC1>[CH3:20][S:17]([N:15]([CH3:16])[C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])[N:7]=1)[C:3]([OH:21])=[O:2])(=[O:18])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68815178HCID 68815178, compound

Product 1

HCID 68814989HCID 68814989, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-(methanesulfonyl-methylamino)-6-(methylpropylamino)-isonicotinic acid methyl ester (796 mg, 2.52 mmoles) in THF (35 mL) and add 1 N lithium hydroxide (12.6 mL). Stir at room temperature for 16 h, acidify with 5 N HCl (2.6 mL), and partition between diethyl ether and water. Wash the diethyl ether layer with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound as a yellow solid (650 mg, 85%).

Workup

  1. custompartition between diethyl ether and water
  2. washWash the diethyl ether layer with saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-fb887a7262fd4ce79127705c9415a93a
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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