Methanesulfonyl chloride → HCID 57942508, compound

HRID 1898146Notes

Reaction equation

HRID 1898146 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][N:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>N1C=CC=CC=1>[CH3:14][S:15]([NH:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][N:13]=1)[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57942293HCID 57942293, compound

Product 1

HCID 57942508HCID 57942508, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

2-Amino-N-methoxy-N-methyl-isonicotinamide (575 mg, 3.16 mmol) was dissolved in pyridine (4 mL), followed by the addition of methanesulfonyl chloride (0.73 mL, 9.48 mmol). The reaction was subsequently warmed to 40° C. and stirred 5 h. The resultant mixture was quenched with 10% HCl, diluted with EtOAc, and the organic layer washed with 10% HCl and saturated sodium bicarbonate. The combined organics were dried with sodium sulfate, concentrated in vacuo, and purified via automated silica gel chromatography to produce the desired sulfonamide.

Workup

  1. customThe resultant mixture was quenched with 10% HCl
  2. additiondiluted with EtOAc
  3. washthe organic layer washed with 10% HCl and saturated sodium bicarbonate
  4. dry with materialThe combined organics were dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified

Sources & evidence

ORD record
ord-b243056d21294b7299c0120f1d82a099
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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