Dimethylformamide → HCID 86650836, compound
Reaction equation
[N:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[CH:4](O)[CH2:3][CH2:2]2.[H-].[Na+].Cl[C:14]1[N:15]=[N:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=2[F:27])=[CH:18][CH:19]=1.CN(C=[O:32])C>>[F:27][C:21]1[CH:22]=[C:23]([CH3:26])[CH:24]=[CH:25][C:20]=1[C:17]1[N:16]=[N:15][C:14]([O:32][CH:2]2[CH2:3][CH2:4][CH:5]3[CH2:9][N:1]2[CH2:8][CH2:7][CH2:6]3)=[CH:19][CH:18]=1Participants
Procedure
A solution of (rac.)-1-Aza-bicyclo[3.3.1]nonan-4-ol (1.3 mmol) in DMF (5 ml) is treated with sodium hydride (60% in mineral oil; 1.3 mmol). After 1 hr at room temperature, a solution of 3-Chloro-6-(2-fluoro-4-methyl-phenyl)-pyridazine (1 mmol) in DMF (30 ml) is added, and the reaction mixture heated to 50 deg. for 16 hrs. After cooling to room temperature, the DMF solution is quenched with a 10% NaCl solution, extracted with ethyl acetate (2×15 ml), followed by sodium chloride solution (20 ml). The ethyl acetate is dried over anhydrous magnesium sulfate, filtered and evaporated to dryness, and the residual oil purified by silica gel column chromatography (eluent: ethyl acetate-methanol-triethylamine (50:10:2) to afford (rac.)-4-[(6-(2-Fluoro-4-methyl-phenyl)-pyridazin-3-yloxy]-1-aza-bicyclo[3.3.1]nonane as a colourless solid. MS (ES+): m/e=328 (MH+)
Workup
- temperaturethe reaction mixture heated to 50 deg. for 16 hrs
- customthe DMF solution is quenched with a 10% NaCl solution
- extractionextracted with ethyl acetate (2×15 ml)
- dry with materialThe ethyl acetate is dried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated to dryness
- customthe residual oil purified by silica gel column chromatography (eluent
Sources & evidence
- ORD record
- ord-be10118195564b1e8abbe685a0ae8c1e
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933090B2
Reaction notes
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