Methanesulfonyl chloride → 2,2,2-Trifluoro-N-[[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl]acetamide

HRID 748292Notes

Reaction equation

HRID 748292 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](O)=[O:4].[NH2:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]2[S:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20](=[O:22])[N:21]=2)[CH:13]=[CH:12][CH:11]=1.CS(Cl)(=O)=O>N1C=CC=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([C:16]2[S:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20](=[O:22])[N:21]=2)[N:15]=1)=[O:4]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 684582972-[6-(Aminomethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

Product 1

HCID 597502522,2,2-Trifluoro-N-[[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl]acetamideYield 68.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-[6-(Aminomethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (350 mg, 0.91 mmol) was dissolved in pyridine (10 ml), and methanesulfonyl chloride (576 mg, 5.04 mmol) was added thereto. The reaction mixture was stirred at room temperature for 3 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (1:1, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (228 mg, 68%) as pale yellow crystals.

Workup

  1. customThe solvent was evaporated
  2. washThe fractions eluted with hexane-ethyl acetate (1:1
  3. customv/v) were collected
  4. concentrationconcentrated
  5. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-54c9e2a8d7af4fec894004e334ff110b
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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