Hydrochloric Acid → (S)-(+)-2-sec-butylamino-6-(methanesulfonyl-methylamino)-isonicotinate potassium salt

HRID 732367Notes

Reaction equation

HRID 732367 reaction equation
C[O:2][C:3](=[O:21])[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][C@H:17]([CH2:19][CH3:20])[CH3:18])[CH:5]=1.[OH-].[K+:23].Cl>O>[K+:23].[C@@H:17]([NH:16][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([N:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH3:11])[N:7]=1)[C:3]([O-:21])=[O:2])([CH2:19][CH3:20])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68814724(S)-2-sec-Butylamino-6-(methanesulfonyl-methylamino)-isonicotinic acid methyl ester

Product 1

HCID 68815289(S)-(+)-2-sec-butylamino-6-(methanesulfonyl-methylamino)-isonicotinate potassium saltYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Heat a mixture of (S)-(+)-2-sec-butylamino-6-(methanesulfonyl-methylamino)-isonicotinic acid methyl ester (12.66 g, 0.04014 mol) and potassium hydroxide (2.7 g, 0.04817 mol, 1.2 eq) until dissolved. Dilute with water (62 mL) and was heat to reflux for 3 h. Cool to room temperature and add 1 N HCl (8 mL). Concentrate and add dichloromethane (300 mL) and stir well. Filter and concentrate filtrate to give the title compound as a yellow solid (13.62 g, 100%).

Workup

  1. temperatureHeat
  2. dissolutionuntil dissolved
  3. temperaturewas heat
  4. temperatureto reflux for 3 h
  5. concentrationConcentrate
  6. additionadd dichloromethane (300 mL)
  7. filtrationFilter
  8. concentrationconcentrate filtrate

Sources & evidence

ORD record
ord-04d0afd8162443319f2b22daf0ce34ca
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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