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

HRID 711267Notes

Reaction equation

HRID 711267 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:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=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:29](=[O:30])[C:28]2[CH:32]=[CH:33][C:25]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][N:19]=3)=[CH:26][CH:27]=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 114583014-Pyrazin-2-ylbenzoic acidHCID 67208623(2'-(Trifluoromethyl)-2,4'-bipyridin-5-yl)methanamine

Product 1

HCID 56598491N-((3-Methyl-2'-(trifluoromethyl)-2,4'-bipyridin-5-yl)methyl)-4-(pyrazin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methanamine 48-1 (40 mg, 0.15 mmol), 4-(pyrazin-2-yl)benzoic acid 58-1 (30 mg, 0.15 mmol) and HATU (57 mg, 0.15 mmol) in DMF (0.9 mL) was added DIEA (0.08 mL, 0.45 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)-4-(pyrazin-2-yl)benzamide 58 as a white powder. MS m/z 450.20 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 9.35 (d, 1H, J=1.6 Hz), 9.30 (t, 1H, J=6.0 Hz), 8.86 (d, 1H, J=4.8 Hz), 8.76 (m, 1H), 8.67 (d, 1H, J=2.4 Hz), 8.57 (m, 1H), 8.30-8.27 (m, 2H), 8.08-8.06 (m, 3H), 7.94 (dd, 1H, J1=5.0 Hz, J2=1.2 Hz), 7.77 (m, 1H), 4.85 (d, 2H, J=6.0 Hz), 2.40 (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-6d716b6cf1d74de4a24c7b8d68ce6200
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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