Triethylamine → HCID 19367104, compound

HRID 1416266Notes

Reaction equation

HRID 1416266 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([CH:12]=[C:13]([CH2:15]Cl)[N:14]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C(N(CC)CC)C>C(O)CO>[Cl:1][C:2]1[C:3]2[N:4]([CH:12]=[C:13]([CH2:15][N:27]3[CH2:26][CH2:25][N:24]([C:21]4[CH:20]=[CH:19][C:18]([F:17])=[CH:23][CH:22]=4)[CH2:29][CH2:28]3)[N:14]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752601-(4-Fluorophenyl)piperazineHCID 193671298-Chloro-2-(chloromethyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 19367104HCID 19367104, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
82.5 °C

Procedure

A mixture of 8-chloro-2-(chloromethyl)-6-trifluoromethylimidazo[1,2-α]pyridine (0.341 g), 1-(4-fluorophenyl)piperazine (Aldrich; 0.264 g), triethylamine (Aldrich; 0.21 mL), and ethylene glycol (2 mL) is stirred for 2.25 h at 80-85° C. After cooling, the mixture is partitioned between water and dichloromethane and the combined inorganic layers are washed with brine, dried with MgSO4, and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (2/98) and the appropriate fractions combined, concentrated, and crystallized from ether/hexane to give 0.339 g of the title compound; mp 91-97° C.; MS m/z 412, 414; IR (mineral oil) 1322, 1161, 1153, 1512, 1171 cm-1 ; 1H NMR (CDCl3) δ2.76, 3.15, 3.87, 6.88, 6.96, 7.41, 7.75, 8.41.

Workup

  1. temperatureAfter cooling
  2. customthe mixture is partitioned between water and dichloromethane
  3. washthe combined inorganic layers are washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed on silica gel
  7. concentrationconcentrated
  8. customcrystallized from ether/hexane

Sources & evidence

ORD record
ord-34b9ad2405e5427193365ec2a25dfa24
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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