Triethylamine → 2-sec-Butylamino-6-methanesulfonyloxy-isonicotinic acid methyl ester

HRID 1436613Notes

Reaction equation

HRID 1436613 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH:6]([NH:10][C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([OH:20])[N:19]=1)[C:14]([OH:16])=[O:15])([CH2:8][CH3:9])[CH3:7].[CH2:21](N(CC)CC)C>ClCCl>[CH3:21][O:15][C:14](=[O:16])[C:13]1[CH:17]=[C:18]([O:20][S:2]([CH3:1])(=[O:4])=[O:3])[N:19]=[C:11]([NH:10][CH:6]([CH2:8][CH3:9])[CH3:7])[CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178448813HCID 178448813, compound

Product 1

HCID 866150112-sec-Butylamino-6-methanesulfonyloxy-isonicotinic acid methyl esterYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add methanesulfonyl chloride (0.1 mL, 1.292 mmol) to a solution of 2-sec-butylamino-6-hydroxy-isonicotinic acid (242 mg, 1.016 mmol) and triethyl amine (0.25 mL, 1.793 mmol) in dichloromethane (15 mL) at 0° C. Stir at room temperature for 15 min, dilute with dichloromethane, wash with saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 15:85 ethyl acetate:hexanes) to give the title compound as a white solid (240 mg, 75%).

Workup

  1. washwash with saturated aqueous sodium chloride
  2. dry with materialdry (magnesium sulfate)
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 15:85 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-05411e19f85c497687371053dec3c1ac
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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