Ethyl formate → HCID 9927855, compound

HRID 2243822Notes

Reaction equation

HRID 2243822 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[N:4]([C:10]([C:12]1[O:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:3][CH2:2]2.[CH2:24]([O:26]C=O)C>>[N:1]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[N:4]([C:10]([C:12]1[O:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][CH:24]=[O:26])=[CH:19][CH:18]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:3][CH2:2]2

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 10425586HCID 10425586, compound

Product 1

HCID 9927855HCID 9927855, compound

Procedure

A mixture of (1,4-diaza-bicyclo[3.2.2]non-4-yl)-5-(4-aminophenyl)-furan-2-yl-methanone (0.50 g; 1.6 mmol) and ethylformate (30 ml) was stirred at reflux for 9 days. The mixture was evaporated. Aqueous sodium hydroxide (20 ml; 1M) was added followed by extraction with dichloromethane (3×20 ml). The crude mixture was purified by silica gel chromatography, using a mixture of dichloromethane:methanol (9:1) and 1% methanol as eluent. The product was isolated as the free base. Yield 0.29 g (53%). Mp. 236° C.

Workup

  1. temperatureat reflux for 9 days
  2. customThe mixture was evaporated
  3. additionAqueous sodium hydroxide (20 ml; 1M) was added
  4. extractionfollowed by extraction with dichloromethane (3×20 ml)
  5. customThe crude mixture was purified by silica gel chromatography
  6. additiona mixture of dichloromethane:methanol (9:1) and 1% methanol as eluent
  7. customThe product was isolated as the free base

Sources & evidence

ORD record
ord-b935ec677be24c0faaa3cbf2f7b2465c
Source dataset
uspto-grants-2010_03
Patent number
US07678788B2

Reaction notes

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