Triethylamine → HCID 23060698, compound

HRID 750160Notes

Reaction equation

HRID 750160 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[C:6]([C:13]([OH:15])=[O:14])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH2:22][CH2:23][C:24]1[CH:32]=[CH:31][C:27]2[O:28][CH2:29][CH2:30][C:26]=2[CH:25]=1.C(N(CC)CC)C>CO>[O:28]1[C:27]2[CH:31]=[CH:32][C:24]([CH2:23][N:22]3[C:6]([C:13]([OH:15])=[O:14])=[C:5]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:4]4[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=4)[C:8]3=[O:12])=[CH:25][C:26]=2[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27353672,3-Dihydro-1-benzofuran-5-ylmethanamineHCID 23060590HCID 23060590, compound

Product 1

HCID 23060698HCID 23060698, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-fluoro-1-oxo-4-phenyl-1H-isochromen-3-carboxylic acid (1 g), 5-aminomethyl-2,3-dihydrobenzo[b]furan (1.1 g), triethylamine (1 ml) and methanol (10 ml) was stirred at 50° C. for 36 hrs. The reaction mixture was concentrated, 1N-hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the residue was added 4N-hydrochloric acid-ethyl acetate solution (5 ml) at room temperature and the mixture was stirred for 12 hrs. The reaction mixture was concentrated under reduced pressure and the residue was purified by recrystallization (ethyl acetate-hexane) to give the title compound (1.2 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition1N-hydrochloric acid was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue was added 4N-hydrochloric acid-ethyl acetate solution (5 ml) at room temperature
  8. stirringthe mixture was stirred for 12 hrs
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. customthe residue was purified by recrystallization (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-942d0586349b4dd5b391525983cbf885
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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