Acetic Acid → HCID 57896692, compound

HRID 2421904Notes

Reaction equation

HRID 2421904 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:27]=[N:26][C:8]2[O:9][CH2:10][CH2:11][N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:7]=2[CH:6]=1)=[NH:4].C(O)(=O)C.[CH3:32][C:33]([CH3:35])=O>>[CH3:32][C:33]1([CH3:35])[O:1][NH:2][C:3]([C:5]2[CH:27]=[N:26][C:8]3[O:9][CH2:10][CH2:11][N:12]([S:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=4)(=[O:15])=[O:14])[C:7]=3[CH:6]=2)=[N:4]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 180AcetoneHCID 178513384HCID 178513384, compound

Product 1

HCID 57896692HCID 57896692, compoundYield 44.7%

Conditions

Temperature
80 °C

Procedure

To a solution of N-hydroxy-1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboximidamide (25 mg, 0.062 mmol) in acetone (2 mL) was added acetic acid (500 μL, 8.73 mmol). The reaction was heated to 80° C. and stirred at that temperature for 48 h. The reaction mixture was concentrated under reduced pressure. The resulting paste was purified by flash column chromatography using a gradient elution of hexanes with 20-100% EtOAc to provide 7-(5,5-dimethyl-2,5-dihydro-1,2,4-oxadiazol-3-yl)-1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (12.3 mg, 0.028 mmol, 44.7% yield) as a white solid. LCMS (+ESI) m/z=443.1 [M+H]+; 1H-NMR (CDCl3) δ 8.45 (d, 1H), 8.38 (br s, 1H), 7.84 (d, 2H), 7.78 (d, 2H), 4.55 (br s, 1H), 4.02 (dd, 2H), 3.91 (dd, 2H), 1.63 (s, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting paste was purified by flash column chromatography
  3. washa gradient elution of hexanes with 20-100% EtOAc

Sources & evidence

ORD record
ord-360b5c10816c48baa83922b278060f61
Source dataset
uspto-grants-2011_06
Patent number
US07960377B2

Reaction notes

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