HCID 19369840, compound → HCID 19369845, compound

HRID 849215Notes

Reaction equation

HRID 849215 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])[C:15]=3[N:14]=[C:13](Cl)[C:12]=2[CH:11]=[CH:10]1>C(CN)O>[CH3:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])[C:15]=3[N:14]=[C:13]([NH:14][CH2:15][CH2:16][OH:22])[C:12]=2[CH:11]=[CH:10]1

Participants

3

Reactant 1

HCID 19369840HCID 19369840, compound

Product 1

HCID 19369845HCID 19369845, compoundYield 162.9%

Reagents, catalysts & solvents 1

HCID 700EthanolamineSolvent

Conditions

Temperature
180 °C

Procedure

1-(2-Methyl-4-fluorophenyl)-4-chloro-6-β,β,β-trifluoroethoxypyrrolo[3,2-c]quinoline(700 mg, 1.7 mmol), prepared by the procedures of Step 1 and Step 2 in the Example 46, was dissolved in ethanolamine(10 ml) in the pressure tube, and the resultant was refluxed at 180° C. for 3 hours. After removing the excess ethanolamine by distillation under reduced pressure, the residue was diluted in dichloromethane(20 ml), and washed with water(15 ml). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to obtain 600 mg of desired compound as solid in 81% of yield.

Workup

  1. customAfter removing the excess ethanolamine
  2. distillationby distillation under reduced pressure
  3. additionthe residue was diluted in dichloromethane(20 ml)
  4. washwashed with water(15 ml)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e164c7a1e2f8450cb6f000f9649a71a9
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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