Methylamine → 6-Methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid methylamide
Reaction equation
[CH3:1][C:2]1[NH:7][CH:6]=[C:5]([C:8](O)=[O:9])[C:4](=[O:11])[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1.[CH3:22][N:23](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>CN1C(=O)CCC1>[CH3:22][NH:23][C:8]([C:5]1[C:4](=[O:11])[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[C:2]([CH3:1])[NH:7][CH:6]=1)=[O:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 6-methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid (preparation 5b, 0.800 g, 2.69 mmol), HBTU (1.07 g, 2.81 mmol), DIPEA (0.78 mL, 4.59 mmol) in NMP (5 mL) is stirred for 30 min. Then, methylamine (5.00 mL of 2M solution in THF, 10.0 mmol) is added and the reaction mixture is stirred for 18 h at room temperature. The reaction mixture is concentrated under reduced pressure and purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.). Yield: 0.20 g (24% of theory); ESI mass spectrum: [M+H]+=311; Retention time HPLC: 1.10 min (V003—003).
Workup
- concentrationThe reaction mixture is concentrated under reduced pressure
- custompurified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.3% NH4OH, 60° C.)
- custom1.10 min (V003—003)
Sources & evidence
- ORD record
- ord-df392951f52b4c6098586bda2a27c914
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102624B2
Reaction notes
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