Diisopropylethylamine → 1-(3-Fluorophenyl)-N-((2'-methyl-[2,4'-bipyridin]-5-yl)methyl)-2-oxo-1,2-dihydropyridine-4-carboxamide

HRID 711280Notes

Reaction equation

HRID 711280 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][NH2:15])=[CH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1.[F:16][C:17]1[CH:18]=[C:19]([N:23]2[CH:28]=[CH:27][C:26]([C:29](O)=[O:30])=[CH:25][C:24]2=[O:32])[CH:20]=[CH:21][CH:22]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[F:16][C:17]1[CH:18]=[C:19]([N:23]2[CH:28]=[CH:27][C:26]([C:29]([NH:15][CH2:14][C:11]3[CH:12]=[CH:13][C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=4)=[N:9][CH:10]=3)=[O:30])=[CH:25][C:24]2=[O:32])[CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67208679(2'-Methyl-[2,4'-bipyridin]-5-yl)methanamineHCID 680798531-(3-Fluorophenyl)-2-oxo-1,2-dihydropyridine-4-carboxylic acid

Product 1

HCID 565976581-(3-Fluorophenyl)-N-((2'-methyl-[2,4'-bipyridin]-5-yl)methyl)-2-oxo-1,2-dihydropyridine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2′-methyl-[2,4′-bipyridin]-5-yl)methanamine 18-2 (14 mg, 0.07 mmol), 1-(3-fluorophenyl)-2-oxo-1,2-dihydropyridine-4-carboxylic acid 89-3 (16 mg, 0.07 mmol), and HATU (29 mg, 0.076 mmol) were added N,N-diisopropylethylamine (DIEA, 17 μL, 0.098 mmol) and DMF (0.5 mL). The solution was stirred overnight at room temperature and subjected to reverse phase preparative HPLC separation to yield 1-(3-fluorophenyl)-N-((2′-methyl-[2,4′-bipyridin]-5-yl)methyl)-2-oxo-1,2-dihydropyridine-4-carboxamide 89. MS m/z 415.2 (M+1).

Workup

  1. customphase preparative HPLC separation

Sources & evidence

ORD record
ord-35afd661f9e7438785a457719f52f6d0
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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