Triethylamine → HCID 67966680, compound

HRID 72470Notes

Reaction equation

HRID 72470 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH:6]1[CH2:9][NH:8][CH2:7]1.C(N(CC)CC)C.Cl[C:21]1[N:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:22]=1[C:23]([OH:25])=[O:24]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH:6]1[CH2:9][N:8]([C:21]2[N:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][C:22]=2[C:23]([OH:25])=[O:24])[CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 121402272-Chloro-5-(trifluoromethyl)nicotinic acidHCID 155219743-(3-Fluorophenoxy)azetidine

Product 1

HCID 67966680HCID 67966680, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-(3-fluorophenoxy)azetidine) (D50) (106.73 mg, 0.638 mmol) and triethylamine (0.11 ml, 0.798 mmol) in methanol (3 ml), 2-Chloro-5-(trifluoromethyl)nicotinic acid (120 mg, 0.532 mmol) was added and the mixture was heated 10 min (2 cycles of 5 min each) under microwave irradiation at 150° C. After solvent evaporation the residue was purified by SPE-Si cartridge (25 g) eluting with a mixture dichloromethane/methanol from 100/0 to 50/50. Collected fraction after solvent evaporation afforded the title compound (D121) (83 mg)

Workup

  1. additionwas added
  2. temperaturethe mixture was heated 10 min (2 cycles of 5 min each)
  3. customunder microwave irradiation at 150° C
  4. customAfter solvent evaporation the residue
  5. customwas purified by SPE-Si cartridge (25 g)
  6. washeluting with a mixture dichloromethane/methanol from 100/0 to 50/50
  7. customCollected fraction
  8. customafter solvent evaporation

Sources & evidence

ORD record
ord-1297006bbebd4fe1974378785fb97602
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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