Diisopropylethylamine → 6-Methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid (5-methanesulfonyl-pyridin-2-ylmethyl)-amide

HRID 512493Notes

Reaction equation

HRID 512493 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.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:55][S:56]([C:59]1[CH:60]=[CH:61][C:62]([CH2:65][NH2:66])=[N:63][CH:64]=1)(=[O:58])=[O:57]>CN1C(=O)CCC1.CO.O>[CH3:55][S:56]([C:59]1[CH:60]=[CH:61][C:62]([CH2:65][NH:66][C:8]([C:5]2[C:4](=[O:11])[C:3]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:19])[F:21])[CH:13]=3)=[C:2]([CH3:1])[NH:7][CH:6]=2)=[O:9])=[N:63][CH:64]=1)(=[O:58])=[O:57]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57354332(5-(Methylsulfonyl)pyridin-2-yl)methanamineHCID 867115326-Methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid

Product 1

HCID 867115356-Methyl-4-oxo-5-(3-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid (5-methanesulfonyl-pyridin-2-ylmethyl)-amide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

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 (1.37 mL, 8.08 mmol) in NMP (5 mL) is stirred for 30 min. Then, C-(5-methanesulfonyl-pyridin-2-yl)-methylamine (0.55 g, 2.95 mmol) is added and the reaction mixture is stirred for 18 h at room temperature. The reaction mixture is diluted with a small amount of MeOH. Upon addition of water a precipitate forms which is collected by filtration and dried. Yield: 0.78 g (62% of theory); ESI mass spectrum: [M+H]+=466; Retention time HPLC: 1.09 min (V003—003).

Workup

  1. filtrationis collected by filtration
  2. customdried
  3. custom1.09 min (V003—003)

Sources & evidence

ORD record
ord-69498e507b9048e49d42a5e9880760f3
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Reaction notes

Loading…