1,4-Dioxane → HCID 57561041, compound
Reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8]([NH2:10])[C:7]([NH2:11])=[C:6]([NH2:12])[CH:5]=1.Br.Br[CH2:15][C:16]([C:18]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][N:19]=1)=O.C([O-])(O)=O.[Na+].O1CCOCC1>O>[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[C:6]([NH2:12])[C:7]2[C:8]([N:9]=1)=[N:10][C:16]([C:18]1[C:23]([C:24]([F:27])([F:25])[F:26])=[CH:22][CH:21]=[CH:20][N:19]=1)=[CH:15][N:11]=2Participants
Conditions
- Temperature
- 100 °C
Procedure
6-Methoxymethyl-2,3,4-triamino-pyridine (353 mg, 2.10 mmol), 2-bromo-1-(3-trifluoromethyl-pyridin-2-yl)-ethanone hydrobromide (771 mg, 2.21 mmol; synthesis described in Example 2E, below), and NaHCO3 (554 mg, 6.59 mmol) are dissolved into a solution of dioxane (20 mL) and water (20 mL). The reaction mixture is stirred 1 hour at room temperature and 3 hours at 100° C. The mixture is cooled and filtered through Celite. The Celite bed is washed with EtOAc (20 mL). The aqueous mixture is extracted with EtOAc (4×100 mL). The combined organic extracts are washed with brine and dried over Na2SO4. The solvent is removed under reduced pressure and the crude product purified by column chromatography on silica gel eluting with acetone/hexanes (1:1) to yield the title compound as a white solid.
Workup
- temperatureThe mixture is cooled
- filtrationfiltered through Celite
- washThe Celite bed is washed with EtOAc (20 mL)
- extractionThe aqueous mixture is extracted with EtOAc (4×100 mL)
- washThe combined organic extracts are washed with brine
- dry with materialdried over Na2SO4
- customThe solvent is removed under reduced pressure
- customthe crude product purified by column chromatography on silica gel eluting with acetone/hexanes (1:1)
Sources & evidence
- ORD record
- ord-d6dc430542294c1a9164c8066b198463
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07488740B2
Reaction notes
Loading…