Water → N-[[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl]propanamide

HRID 499470Notes

Reaction equation

FC(F)(F)C(O)=O.[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.[C:27](Cl)(=[O:30])[CH2:28][CH3:29].C(OCC)(=O)C.O>CN(C)C(=O)C>[O:22]=[C:20]1[C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[S:17][C:16]([C:14]2[N:15]=[C:10]([CH2:9][NH:8][C:27](=[O:30])[CH2:28][CH3:29])[CH:11]=[CH:12][CH:13]=2)=[N:21]1

Participants

Conditions

Temperature: 60 °C

Procedure

2-[6-(Aminomethyl)-2-pyridyl]-4H-1,3-benzothiazine-4-one trifluoroacetic acid salt (500 mg, 1.3 mmol) was dissolved in N,N-dimethylacetamide (10 ml), and propionyl chloride (370 mg, 4.0 mmol) was added thereto. The reaction mixture was stirred at 60° C. for 16 hrs and combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with methanol-ethyl acetate (1:20, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (224 mg, 53%) as white crystals.

Workup

washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated
washThe fractions eluted with methanol-ethyl acetate (1:20
customv/v) were collected
concentrationconcentrated
customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record: ord-a9d91ca3eaa84abc85612345561badff
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767665B2

Reaction notes

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