Formic acid, propyl ester → HCID 18416050, compound

HRID 990985Notes

Reaction equation

HRID 990985 reaction equation
[Cl-].[NH:2]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH2:7][CH2:6][C:5]=2[C:4]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([CH2:21][NH3+:22])[CH:16]=2)=[N:3]1.C(N(CC)CC)C.[CH:30](OCCC)=[O:31]>C(O)C.ClCCl>[NH:2]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH2:7][CH2:6][C:5]=2[C:4]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([CH2:21][NH:22][CH:30]=[O:31])[CH:16]=2)=[N:3]1

Participants

6

Reactant 3

HCID 8073Formic acid, propyl esterHCID 8471TriethylamineHCID 18415862HCID 18415862, compound

Product 1

HCID 18416050HCID 18416050, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

The product from Example 19 (100 mg) was suspended in propyl form ate (10 ml) and ethanol (1.5 ml). This mixture was boiled under reflux and after 2 minutes triethylamine (0.5 ml) was added. The mixture was boiled under reflux for 4 hours and then cooled and diluted with dichloromethane (50 ml). The mixture was washed with water, then dried, filtered and evaporated to give a residue which was triturated with ether and dichloromethane to give N-{[4-(4,5-dihydro-1H-benzo[g]-indazol-3-yl)-2-pyridyl]methyl}formamide.

Workup

  1. additionwas added
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. washThe mixture was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto give a residue which
  9. customwas triturated with ether and dichloromethane

Sources & evidence

ORD record
ord-cbef3fd27cb1490c88e16973edaad9da
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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