2,3-Dihydro-1,4-benzothiazine → HCID 10456089, compound

HRID 2105986Notes

Reaction equation

HRID 2105986 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[S:21]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[NH:24][CH2:23][CH2:22]1>CN(C)C=O.C(OCC)C>[S:21]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]([CH2:12][C:10]([OH:11])([CH2:9][C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:19][CH3:20])([CH3:18])[CH3:17])[C:13]([F:16])([F:15])[F:14])[CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 1510642,3-Dihydro-1,4-benzothiazineHCID 160992392-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Product 1

HCID 10456089HCID 10456089, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (118 mg) and 3,4-dihydro-2H-1,4-benzothiazine (H. I. El-Subbagh et al., Arch. Pharm. Med. Chem., 1999, 332, pp. 19-24) (122 mg) in dimethylformamide (1 mL) was heated at 140° C. for 73 hours. The resulting mixture was diluted with diethyl ether, washed with saturated aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by radial chromatography with a chromatotron (eluted with 0% to 1% ethyl acetate-hexanes) to give the title compound as a white solid (53.5 mg), m.p. 103° C.-104° C.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate, water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by radial chromatography with a chromatotron (eluted with 0% to 1% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-62cdf80f35ed43c5a071c4abb9ff41d5
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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