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

HRID 711261Notes

Reaction equation

HRID 711261 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][N:10]=2)[CH:6]=[CH:5][N:4]=1.[N:19]1[CH:24]=[CH:23][N:22]=[CH:21][C:20]=1[C:25]1[CH:26]=[CH:27][C:28]([C:31]([OH:33])=O)=[N:29][CH:30]=1.[CH3:34]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:34][C:14]1[C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:8]=2)=[N:10][CH:11]=[C:12]([CH2:15][NH:16][C:31](=[O:33])[C:28]2[CH:27]=[CH:26][C:25]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][N:19]=3)=[CH:30][N:29]=2)[CH:13]=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 639681575-(Pyrazin-2-yl)pyridine-2-carboxylic acidHCID 67208623(2'-(Trifluoromethyl)-2,4'-bipyridin-5-yl)methanamine

Product 1

HCID 56599159N-((3-Methyl-2'-(trifluoromethyl)-2,4'-bipyridin-5-yl)methyl)-5-(pyrazin-2-yl)picolinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methanamine 48-1 (27 mg, 0.10 mmol), 5-(pyrazin-2-yl)picolinic acid 41-4 (21 mg, 0.10 mmol) and HATU (38 mg, 0.10 mmol) in DMF (0.6 mL) was added DIEA (0.05 mL, 0.30 mmol). The mixture was stirred at room temperature for 2 hours. The solvent was removed by rotary evaporation. The crude product was purified by reverse phase HPLC to give N-((3-methyl-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methyl)-5-(pyrazin-2-yl)picolinamide 55 as a white powder. MS m/z 451.20 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 9.67 (t, 1H, J=6.0 Hz), 9.45 (d, 1H, J=1.2 Hz), 9.40 (d, 1H, J=0.8 Hz), 8.87-8.82 (m, 2H), 8.74-8.57 (m, 2H), 8.57 (m, 1H), 8.20 (d, 1H, J=8.4 Hz), 8.05 (m, 1H), 7.93 (dd, 1H, J1=9.6 Hz, J2=1.2 Hz), 7.77 (m, 1H), 4.59 (d, 2H, J=6.0 Hz), 2.38 (s, 3H).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-c6c48b2f2e794d979d6a4f4c6e78d48f
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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