Triethylamine → HCID 69157400, compound

HRID 750142Notes

Reaction equation

HRID 750142 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[N:7]([CH2:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[C:8](=[O:23])[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Br:22])=[CH:11][CH:10]=2)=[O:5].C(N(CC)CC)C.[CH3:38][N:39]=[C:40]=[O:41]>O1CCCC1>[CH3:2][O:3][C:4]([C:6]1[N:7]([CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:40](=[O:41])[NH:39][CH3:38])[CH2:27][CH2:26]2)[C:8](=[O:23])[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Br:22])=[CH:11][CH:10]=2)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 69155731HCID 69155731, compound

Product 1

HCID 69157400HCID 69157400, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-1-oxo-4-phenyl-2-(piperidin-4-ylmethyl)-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester hydrochloride (100 mg) in tetrahydrofuran (5 ml) were added triethylamine (0.06 ml) and methylisocyanate (0.018 ml), and the mixture was stirred at room temperature for 24 hrs. The solvent was evaporated under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by preparative HPLC to give the title compound (34 mg, 33%).

Workup

  1. customThe solvent was evaporated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. customdried
  6. additionby adding sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b40886412fd045c186d8e72f91c0c1e0
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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