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

HRID 1436495Notes

Reaction equation

HRID 1436495 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-ed397be40b5e4d2bb54594e2a176b7b3
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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