Diethyl squarate → HCID 18379722, compound

HRID 2299078Notes

Reaction equation

HRID 2299078 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[N:7][CH:8]=1.[CH2:12]([O:14][C:15]1[C:16](=O)[C:17](=[O:22])[C:18]=1[O:19]CC)[CH3:13]>CCO>[CH2:12]([O:14][C:15]1[C:18](=[O:19])[C:17](=[O:22])[C:16]=1[NH:9][C:5]1[CH:6]=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=1)[CH3:13]

Participants

4

Reactant 2

HCID 123228Diethyl squarateHCID 140519365-(Trifluoromethyl)pyridin-3-amine

Product 1

HCID 18379722HCID 18379722, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product from Example 52A (2.98 g, 18.4 mmol) and 3,4,-diethoxy-3-cyclobutene-1,2-dione (3.13 g, 18.4 mmol) in EtOH (50 mL) was heated at reflux for 48 hours. The reaction mixture was filtered while still hot and the filtrate was absorbed onto silica gel. The crude material was purified by chromatography, eluting with EtOAc/hexanes (3:1) to provide 2.00 g (38% yield) of the desired compound as colorless crystals.

Workup

  1. temperatureat reflux for 48 hours
  2. filtrationThe reaction mixture was filtered while still hot and the filtrate
  3. customwas absorbed onto silica gel
  4. customThe crude material was purified by chromatography
  5. washeluting with EtOAc/hexanes (3:1)

Sources & evidence

ORD record
ord-e018f220237f4f6dadba1c45ef1f705a
Source dataset
uspto-grants-2002_12
Patent number
US06495576B2

Reaction notes

Loading…