Potassium Carbonate → HCID 22379910, compound

HRID 895566Notes

Reaction equation

HRID 895566 reaction equation
Cl[CH2:2][C:3]1[N:4]([CH2:16][CH3:17])[C:5]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:8]=[CH:7][C:6]=2[N:15]=1.C([O-])([O-])=O.[K+].[K+].[NH:24]1[CH:28]=[CH:27][N:26]=[C:25]1[C:29]1[S:30][CH:31]=[CH:32][N:33]=1>CN(C=O)C>[CH2:16]([N:4]1[C:5]2[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:8]=[CH:7][C:6]=2[N:15]=[C:3]1[CH2:2][N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[C:29]1[S:30][CH:31]=[CH:32][N:33]=1)[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 222603952-(1H-Imidazol-2-yl)-1,3-thiazoleHCID 22379927HCID 22379927, compound

Product 1

HCID 22379910HCID 22379910, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-Chloromethyl-1-ethyl-6-trifluoromethyl-1H-imidazo[4,5-c]pyridine (1 g, 3.8 mmol) in anhydrous DMF (15 mL) were added K2CO3 (2.68 g, 19 mmol), and 2-(1H-imidazol-2-yl)-thiazole (555 mg, 3.8 mmol) and stirred at room temperature for 48 h. The crude residue after usual work up was purified eluting with 5% MeOH-CH2Cl2 containing few drops of NH4OH to afford1-ethyl-2-{[2-(1,3-thiazol-2-yl)-1H-imidazol-1-yl]methyl}-6-(trifluoromethyl)-1H-imidazo[4,5-c]pyridine (800 mg, 80 %); 1H NMR (CD3OD): δ 8.83 (s, 1H), 8.14 (s, 1H), 7.71 (d, J=2.7 Hz, 1H), 7.53 (d, J=2.7 Hz, 1H), 7.45 (d, J=0.9 Hz, 1H), 7.19 (d, J=0.9 Hz, 1H), 6.30 (s, 2H), 4.54 (q, J=5.4 Hz, 2H), 1.46 (t, J=5.4 Hz, 3H); m/z 379 [M+1]

Workup

  1. customThe crude residue after usual work up was purified
  2. washeluting with 5% MeOH-CH2Cl2 containing few drops of NH4OH to afford1-ethyl-2-{[2-(1,3-thiazol-2-yl)-1H-imidazol-1-yl]methyl}-6-(trifluoromethyl)-1H-imidazo[4,5-c]pyridine (800 mg, 80 %)

Sources & evidence

ORD record
ord-ae4ca957f877460d92aec592c834857a
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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