Diisopropylethylamine → N-((2',3-dimethyl-2,4'-bipyridin-5-yl)methyl)-5-(pyrazin-2-yl)picolinamide

HRID 711269Notes

Reaction equation

HRID 711269 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.[CH3:16][C:17]1[CH:22]=[C:21]([C:23]2[C:28]([CH3:29])=[CH:27][C:26]([CH2:30][NH2:31])=[CH:25][N:24]=2)[CH:20]=[CH:19][N:18]=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>[CH3:16][C:17]1[CH:22]=[C:21]([C:23]2[C:28]([CH3:29])=[CH:27][C:26]([CH2:30][NH:31][C:13](=[O:15])[C:10]3[CH:9]=[CH:8][C:7]([C:2]4[CH:3]=[N:4][CH:5]=[CH:6][N:1]=4)=[CH:12][N:11]=3)=[CH:25][N:24]=2)[CH:20]=[CH:19][N:18]=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 66632694(2',3-Dimethyl-[2,4'-bipyridin]-5-yl)methanamine

Product 1

HCID 56597107N-((2',3-dimethyl-2,4'-bipyridin-5-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 (20 mg, 0.1 mmol), (2′,3-dimethyl-2,4′-bipyridin-5-yl)methanamine 63-2 (21 mg, 0.1 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) (38 mg, 0.1 mmol) in DMF (1.0 mL) was added DIEA (0.053 mL, 0.3 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′,3-dimethyl-2,4′-bipyridin-5-yl)methyl)-5-(pyrazin-2-yl)picolinamide 63 as white solid. MS m/z 397.2 (M+1). 1H NMR 400 MHz (DMSO-d6) δ 9.59 (t, 1H), 9.39 (d, 1H), 9.33 (d, 1H), 8.76 (m, 1H), 8.68 (m, 2H), 8.45 (d, 1H), 8.15 (d, 1H), 7.65 (d, 1H), 7.34 (b, 1H), 7.27 (d, 1H), 4.51 (d, 2H), 2.46 (s, 3H), 2.26 (s, 3H).

Workup

  1. custompurified by HPLC

Sources & evidence

ORD record
ord-b0df3ca3812a4c02b7445480827628b4
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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