Ammonium Acetate → HCID 57617810, compound

HRID 2421855Notes

Reaction equation

HRID 2421855 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[CH:33]=[CH:32][C:14]2[S:15][CH2:16][CH2:17][N:18]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:13]=2[CH:12]=1)=[O:10].C([O-])(=O)C.[NH4+]>CN(C=O)C>[F:29][C:28]([F:31])([F:30])[C:25]1[CH:24]=[CH:23][C:22]([S:19]([N:18]2[CH2:17][CH2:16][S:15][C:14]3[CH:32]=[CH:33][C:11]([C:9]4[O:10][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=5[N:8]=4)=[CH:12][C:13]2=3)(=[O:21])=[O:20])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 67242918HCID 67242918, compound

Product 1

HCID 57617810HCID 57617810, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-hydroxyphenyl)-4-(4-(trifluoromethyl)phenylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazine-6-carboxamide (25 mg, 51 μmol) was dissolved in 1 mL of DMF. Ammonium acetate (39 mg, 506 μmol) was added and the reaction was subjected to microwave irradiation (150° C., 25 min). LCMS analysis of the reaction mixture showed consumption of starting material. The reaction mixture was 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 organic layers were combined, dried over anhydrous Na2SO4, filtered and evaporated. The residue was purified by flash column chromatography with gradient elution of hexanes with 10-60% EtOAc to provide 2-(4-(4-(trifluoromethyl)phenylsulfonyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)benzo[d]oxazole (1.4 mg, 2.9 μmol, 6% yield) as a yellow oil. LCMS (+ESI) m/z=477.4 [M+H]+; 1H-NMR (CDCl3) δ 7.7-7.9 (m, 6H), 7.40 (d, 2H), 7.30 (d, 1H), 7.05 (dd, 1H), 6.80 (d, 1H), 3.50 (t, 2H), 3.05 (t, 2H).

Workup

  1. customthe reaction was subjected to microwave irradiation (150° C., 25 min)
  2. customconsumption of starting material
  3. additionThe reaction mixture was diluted with saturated aqueous sodium bicarbonate (1 mL) and EtOAc (2 mL)
  4. customThe organic layer was removed
  5. extractionthe aqueous layer extracted with EtOAc (2 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash column chromatography with gradient elution of hexanes with 10-60% EtOAc

Sources & evidence

ORD record
ord-6689566ba1b64687a0bc9a1b2cd1ab36
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

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