Diisopropylethylamine → N-((2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methyl)-5-(pyrazin-2-yl)picolinamide

HRID 711266Notes

Reaction equation

HRID 711266 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10]([C:13]([OH:15])=O)=[N:11][CH:12]=1.[NH2:16][CH2:17][C:18]1[CH:23]=[CH:22][N:21]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[C:20](=[O:34])[CH:19]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C>CN(C=O)C.CS(C)=O>[O:34]=[C:20]1[CH:19]=[C:18]([CH2:17][NH:16][C:13](=[O:15])[C:10]2[CH:9]=[CH:8][C:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)=[CH:12][N:11]=2)[CH:23]=[CH:22][N:21]1[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=1

Participants

7

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 639681575-(Pyrazin-2-yl)pyridine-2-carboxylic acidHCID 672086134-(aminomethyl)-1-(2-(trifluoromethyl)pyridin-4-yl)pyridin-2(1H)-one

Product 1

HCID 56597950N-((2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methyl)-5-(pyrazin-2-yl)picolinamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-(pyrazin-2-yl)picolinic acid 41-4 (28 mg, 0.14 mmol), 4-(aminomethyl)-1-(2-(trifluoromethyl)pyridin-4-yl)pyridin-2(1H)-one 56-7 (35 mg, 0.13 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) (49 mg, 0.13 mmol) in DMF (1.0 mL) was added DIEA (0.09 mL, 0.52 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted into DMSO and purified by HPLC to give N-((2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methyl)-5-(pyrazin-2-yl)picolinamide 56 as a white solid. MS m/z 453.2 (M+1). 1H NMR 400 MHz (DMSO-d6) δ 9.57 (t, 1H), 9.40 (d, 1H), 9.36 (dd, 1H), 8.86 (d, 1H), 8.77 (dd, 1H), 8.69 (m, 2H), 8.16 (dd, 1H), 8.07 (d, 1H), 7.84 (dd, 1H), 7.73 (d, 1H), 6.37 (dd, 1H), 6.31 (b, 1H), 4.36 (d, 2H).

Workup

  1. custompurified by HPLC

Sources & evidence

ORD record
ord-2a014d039daa411d979d421ff5bb6638
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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