Reaction equation
Cl.Cl.[F:3][C:4]([F:16])([F:15])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][NH2:14])[CH:8]=1.[C:17]([NH:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][N:29]=1)[C:24](O)=[O:25])(=[O:19])[CH3:18].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[C:17]([NH:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][N:29]=1)[C:24]([NH:14][CH2:13][C:9]1[CH:8]=[C:7]([O:6][CH2:5][C:4]([F:3])([F:15])[F:16])[CH:12]=[CH:11][N:10]=1)=[O:25])(=[O:19])[CH3:18]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of (4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methanamine dihydrochloride (20 mg, 0.070 mmol, Amine-2), 2-acetamidoisonicotinic acid (15 mg, 0.084 mmol) and N,N-diisopropylethylamine (0.049 mL, 0.28 mmol) in N,N-dimethylformamide (0.5 mL) is added a solution of HBTU (40 mg, 0.11 mmol) in N,N-dimethylformamide (0.5 mL) at room temperature. After stirring at room temperature for 2 hours, the mixture is poured into water (2 mL) and extracted with ethyl acetate (3 mL). The organic layer is dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on NH-silica gel eluting with ethyl acetate and then by preparative LC-MS to give 9.8 mg (38% yield) of the title compound.
Workup
- extractionextracted with ethyl acetate (3 mL)
- dry with materialThe organic layer is dried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue is purified by column chromatography on NH-silica gel eluting with ethyl acetate
Sources & evidence
- ORD record
- ord-29829bd2666844e5b2e0022e1a8989de
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302991B2
Linked notes
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