Cyclohexanemethylamine → Cyclohexyl-6-methyl-2-oxo-5-phenyl-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide
Reaction equation
[CH:1]1(CN)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][C:10]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C:14](=[O:26])[C:13]([C:27](O)=[O:28])=[CH:12][C:11]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C[N:37](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH:1]1([C:12]2[C:11]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:10]([CH3:9])[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=3)[C:14](=[O:26])[C:13]=2[C:27]([NH2:37])=[O:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
7
Reactant 5
HCID 76688Cyclohexanemethylamine
HCID 81531Diisopropylethylamine
HCID 181649HOAt
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 667252216-Methyl-2-oxo-5-phenyl-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acidProduct 1
Reagents, catalysts & solvents 1
Procedure
(Cyclohexylmethyl)amine in NMP (135 μl, 0.3M, 0.04 mmol) was added to a mixture of 6-methyl-2-oxo-5-phenyl-1-[3-(trifluoromethyl)-phenyl]-1,2-dihydro-pyridine-3-carboxylic acid (12 mg, 0.03 mmol), HATU (15 mg, 0.04 mmol), HOAT (7 mg, 0.04 mmol) and DIEA (13 mg, 0.1 mmol) in NMP (160 μl). The reaction mixture was stirred for 17 h at room temperature. The solvent was removed in vacuo, and the residue was dissolved in acetonitrile/water, 50/50, to a total volume of 1.6 ml, and purified using preparative HPLC to give the title compound (7 mg, 50%).
Workup
- customThe solvent was removed in vacuo
- dissolutionthe residue was dissolved in acetonitrile/water
- custom50/50, to a total volume of 1.6 ml, and purified
Sources & evidence
- ORD record
- ord-18af09e2fb1b44a19fc866e223d204be
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501784B2
Reaction notes
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