Ammonium Acetate → HCID 57617804, compound

HRID 2421854Notes

Reaction equation

HRID 2421854 reaction equation
O=[C:2]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:3][NH:4][C:5]([C:7]1[CH:29]=[CH:28][C:10]2[S:11][CH2:12][CH2:13][N:14]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:9]=2[CH:8]=1)=O.C([O-])(=O)C.[NH4+:40]>CN(C=O)C.C(=O)(O)[O-].[Na+].CCOC(C)=O>[C:30]1([C:2]2[NH:40][C:5]([C:7]3[CH:29]=[CH:28][C:10]4[S:11][CH2:12][CH2:13][N:14]([S:15]([C:18]5[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][CH:19]=5)(=[O:17])=[O:16])[C:9]=4[CH:8]=3)=[N:4][CH:3]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 2

HCID 517165Ammonium AcetateHCID 67241747HCID 67241747, compound

Product 1

HCID 57617804HCID 57617804, compoundYield 6.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of N-(2-oxo-2-phenylethyl)-4-(4-(trifluoromethyl)phenylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxamide (20 mg, 38 μmol) in DMF (1 mL) was added ammonium acetate (30 mg, 380 μmol). The reaction mixture was subjected to microwave irradiation (150° C., 15 min). LCMS analysis of the reaction mixture indicated nearly complete conversion of the starting material. The reaction mixture diluted with saturated aqueous sodium bicarbonate (1 mL) and EtOAc (2 mL). The organic layer was removed and the aqueous layer extracted with EtOAc (2 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified by flash column chromatography using a gradient elution of hexanes with 10-60% EtOAc to provide 6-(5-phenyl-1H-imidazol-2-yl)-4-(4-(trifluoro-methyl)phenylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazine (1.2 mg, 2.4 μmol, 6% yield) as a yellow oil. LCMS (+ESI) m/z=502.5 [M+H]+; 1H-NMR (CDCl3) δ 8.10 (m, 2H), 7.90 (d, 2H), 7.80 (d, 2H), 7.4-7.5 (m, 4H), 7.25 (d, 1H), 7.00 (dd, 1H), 6.76 (d, 1H), 3.53 (t, 2H), 3.08 (t, 2H).

Workup

  1. customThe reaction mixture was subjected to microwave irradiation (150° C., 15 min)
  2. customThe organic layer was removed
  3. extractionthe aqueous layer extracted with EtOAc (2 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by flash column chromatography
  8. washa gradient elution of hexanes with 10-60% EtOAc

Sources & evidence

ORD record
ord-5585980c6f524566871bdf8dfcd15e42
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

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