Trifluoroacetic acid → 6-(1,4-Diazepan-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine
Reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:34])([F:33])[C:10]1[N:18]2[C:13]([CH:14]=[CH:15][C:16]([N:19]3[CH2:25][CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)=[N:17]2)=[N:12][N:11]=1.C(=O)(O)[O-].[Na+]>ClCCl>[N:19]1([C:16]2[CH:15]=[CH:14][C:13]3=[N:12][N:11]=[C:10]([C:9]([F:8])([F:34])[F:33])[N:18]3[N:17]=2)[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1Participants
Procedure
Trifluoroacetic acid (8 mL, 103.68 mmol) was added to a mixture of tert-butyl 4-[3-(trifluoromethyl)-[1,2,4]triazolo[3,4-f]pyridazin-6-yl]-1,4-diazepane-1-carboxylate (5.9 g, 15.3 mmol) and dichloromethane (80 mL) at ambient temperature and the resulting solution was stirred at ambient temperature for 6 hours. The reaction mixture was evaporated to give an involatile residue that was treated with saturated aqueous sodium bicarbonate solution (100 mL) and then extracted with dichloromethane (4×200 mL). The organic phases were combined and dried over Na2SO4, filtered, and evaporated to give 6-(1,4-diazepan-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[3,4-f]pyridazine (3.8 g, 86.9%) as a white solid. 1H NMR (300.132 MHz, DMSO) δ 1.68-1.84 (m, 2H), 2.69 (t, 2H), 2.88 (t, 2H), 3.60-3.79 (m, 4H), 7.46 (d, 1H), 8.19 (d, 1H); m/z. 287 (M+H)+.
Workup
- customThe reaction mixture was evaporated
- customto give an involatile residue that
- extractionextracted with dichloromethane (4×200 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-d9c2327acb94431ca7eec7ae2d43d7d6
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003649B2
Reaction notes
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