Cyclohexanemethylamine → N-(Cyclohexylmethyl)-6-methyl-2-oxo-5-phenyl-1-[3-(trifluoromethyl)phenyl]1,2-dihydropyridine-3-carboxamide

HRID 559820Notes

Reaction equation

HRID 559820 reaction equation
[CH:1]1([CH2:7][NH2:8])[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.CN(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([CH2:7][NH:8][C:27]([C:13]2[C:14](=[O:26])[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=3)[C:10]([CH3:9])=[C:11]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:12]=2)=[O:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 76688CyclohexanemethylamineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 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 acid

Product 1

HCID 66725325N-(Cyclohexylmethyl)-6-methyl-2-oxo-5-phenyl-1-[3-(trifluoromethyl)phenyl]1,2-dihydropyridine-3-carboxamideYield 50%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

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

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in acetonitrile/water
  3. custom50/50, to a total volume of 1.6 ml, and purified

Sources & evidence

ORD record
ord-688bbe15ebc84f4f981858c74d128d4b
Source dataset
uspto-grants-2011_11
Patent number
US08063073B2

Reaction notes

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