Water → (S)-2-sec-Butylamino-6-(methanesulfonyl-methylamino)-isonicotinic acid methyl ester

HRID 732366Notes

Reaction equation

HRID 732366 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[N:7]=[C:6]([NH:15][C@H:16]([CH2:18][CH3:19])[CH3:17])[CH:5]=1.[C:21](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([N:10]([S:11]([CH3:14])(=[O:13])=[O:12])[CH3:21])[N:7]=[C:6]([NH:15][C@H:16]([CH2:18][CH3:19])[CH3:17])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68814626(S)-2-sec-butylamino-6-methanesulfonylamino-isonicotinic acid methyl ester

Product 1

HCID 68814724(S)-2-sec-Butylamino-6-(methanesulfonyl-methylamino)-isonicotinic acid methyl esterYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treat a mixture of (s)-(+)-2-sec-butylamino-6-methanesulfonylamino-isonicotinic acid methyl ester (13.63 g, 0.04523 mol) and potassium carbonate (12.50 g, 0.09046 mol) in DMF (42 mL) with iodomethane (7.90 g, 0.05563 mol). Stir at room temperature for 18 h, and add water (200 mL). The aqueous layer was extracted with methyl tert-butyl ether (5×150 mL). Wash the combined organic layers with 1 N lithium chloride (5×100 mL), dry (magnesium sulfate) and concentrate to give the title compound as a solid (13.19 g, 92%).

Workup

  1. additionTreat
  2. extractionThe aqueous layer was extracted with methyl tert-butyl ether (5×150 mL)
  3. washWash the combined organic layers with 1 N lithium chloride (5×100 mL)
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-77e9422518ec49e0808e3fed518a8b32
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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