4-Aminopyridine → 1-Ethyl-2-(pyridin-4-ylaminomethyl)-6-(3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 2246458Notes

Reaction equation

HRID 2246458 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[CH2:18][C:19]1[N:20]([CH2:40][CH3:41])[C:21]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)[N:24]=[C:23]([C:37]#[N:38])[C:22]=2[N:39]=1>CN(C=O)C>[CH2:40]([N:20]1[C:21]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)[N:24]=[C:23]([C:37]#[N:38])[C:22]=2[N:39]=[C:19]1[CH2:18][NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)[CH3:41]

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 81531DiisopropylethylamineHCID 685169312-Chloromethyl-1-ethyl-6-(3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Product 1

HCID 177472001-Ethyl-2-(pyridin-4-ylaminomethyl)-6-(3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrileYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Aminopyridine (26 mg, 0.27 mmol) was added to a solution of diisopropylethylamine (0.24 mL, 1.37 mmol) and 2-chloromethyl-1-ethyl-6-(3-trifluoromethy-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (0.100 g, 0.27 mmol) in DMF (3 mL). The mixture was heated at 80° C. for 2 hours, than filtered. The precipitate was washed with water, then isopropyl ether, dried to afford the title compound (55 mg, 47%) as a solid (mp=340° C.). 1H NMR (DMSO-d6) δ: 8.84 (s, 1H); 8.6-8.5 (m, 2H); 8.31 (d, J=8 Hz, 2H); 7.9-7.7 (m, 2H); 6.97 (d, J=8 Hz, 2H); 5.98 (s, 2H); 4.51 (q, J=7 Hz, 2H); 1.45 (t, J=7 Hz, 3H). MS m/z: 423 (M+1).

Workup

  1. filtrationthan filtered
  2. washThe precipitate was washed with water
  3. dry with materialisopropyl ether, dried

Sources & evidence

ORD record
ord-a72b045ae8c348de81a968b6e4dd80ce
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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