1,8-Diazabicyclo(5.4.0)undec-7-ene → 6,7-Difluoro-2-[4-(trifluoromethyl)pyridin-3-yl][1,2,4]triazolo[1,5-a]pyridine
Reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[C:8]([CH:9]=O)=[CH:7][N:6]=[CH:5][CH:4]=1.CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:26][N+:27]1[CH:32]=[C:31]([F:33])[C:30]([F:34])=[CH:29][C:28]=1[NH2:35].N12CCCN=C1CCCCC2>C(O)C>[F:33][C:31]1[C:30]([F:34])=[CH:29][C:28]2[N:27]([N:26]=[C:9]([C:8]3[CH:7]=[N:6][CH:5]=[CH:4][C:3]=3[C:2]([F:12])([F:11])[F:1])[N:35]=2)[CH:32]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4-(trifluoromethyl)nicotinaldehyde was added to a solution of 1,2-diamino-4,5-difluoropyridinium 2,4,6-trimethylbenzenesulfonate (47-4; 0.2 g, 0.000579 mol) in ethanol (20 mL) while stirring, followed by the addition of 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction mixture was stirred for 12 h at RT. It was then concentrated under vacuum, diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The collected organic parts were concentrated under vacuum to afford the crude product, which was purified by silica gel column chromatography to afford the title compounds. 1H NMR (400 MHz, DMSO) δ 8.20 (s, 1H), 9.09-9.06 (m, 1H), 9.03-9.02 (d, J=4 Hz, 1H), 7.99-7.77 (d, J=8 Hz, 1H), 7.61-7.55 (m, 1H). HPLC purity-99.13%, MS (M+1): 301.1.
Workup
- stirringThe reaction mixture was stirred for 12 h at RT
- concentrationIt was then concentrated under vacuum
- additiondiluted with water (50 mL)
- extractionextracted with ethyl acetate (2×50 mL)
- concentrationThe collected organic parts were concentrated under vacuum
- customto afford the crude product, which
- customwas purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-ea0e3f6ac7164e2ea4dc062f6bbd3c0b
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193724B2
Reaction notes
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