Reaction equation
[Br:1][C:2]1[C:3](=[O:22])[C:4]([C:19]([OH:21])=O)=[CH:5][N:6]([CH:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[CH3:10])[C:7]=1[CH3:8].[CH3:23][N:24](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN>CN(C=O)C.CO>[CH3:23][NH:24][C:19]([C:4]1[C:3](=[O:22])[C:2]([Br:1])=[C:7]([CH3:8])[N:6]([CH:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=2)[CH3:10])[CH:5]=1)=[O:21]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5-bromo-1-[1-(4-cyano-phenyl)-ethyl]-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 2b, 0.51 g, 1.41 mmol), HBTU (0.620 g, 1.64 mmol), DIPEA (0.50 mL, 2.93 mmol) in DMF (2.7 g) is stirred for 30 min. Then, methylamine (1.6 mL of 2M solution in THF, 3.20 mmol) is added and the reaction mixture is stirred for 18 h at room temperature. The reaction mixture is diluted with MeOH and purified by preparative reversed-phase HPLC (XBridge, gradient of acetonitrile in water, 0.3% NH4OH, 60° C.). Yield: 0.31 g (59% of theory); ESI mass spectrum: [M+H]+=374 (bromine isotope pattern); Retention time HPLC: 0.70 min (Z011_S03).
Workup
- custompurified by preparative reversed-phase HPLC (XBridge, gradient of acetonitrile in water, 0.3% NH4OH, 60° C.)
- custom0.70 min (Z011_S03)
Sources & evidence
- ORD record
- ord-95e64d680a1147c583a188d6ca0dfb7d
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102624B2
Linked notes
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