Sodium Chloride → HCID 54401037, compound

HRID 1935060Notes

Reaction equation

HRID 1935060 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:15])[CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][C:9]([C:13]#[N:14])=[CH:8]2.CC[N:18]([CH:22]([CH3:24])[CH3:23])C(C)C.[Br:25][CH2:26]/[CH:27]=[CH:28]/[C:29](Cl)=[O:30].[Cl-].[Na+]>C1COCC1>[Br:25][C:26]1[CH:24]=[C:22]([NH:18][C:8]2[C:7]3[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([NH:15][C:29](=[O:30])[CH:28]=[CH:27][CH2:26][Br:25])[CH:6]=3)[N:11]=[CH:10][C:9]=2[C:13]#[N:14])[CH:23]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 11263885(E)-4-Bromo-2-butenoyl ChlorideHCID 86754955HCID 86754955, compound

Product 1

HCID 54401037HCID 54401037, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1.05 g (2.8 mmol) of 4-[3-bromo-phenyl)amino]-8-methoxy-6-amino-3-quinolinecarbonitrile and 3.9 ml (22.4 mmol) of Hunig's base in 50 ml of dry THF at 0° C., with stirring, was added a THF solution containing 4.11 g (22.4 mmol) of 4-bromo crotonylchloride dropwise. The mixture was stirred for additional 1 hour at 0° C. 50 mL of saturated sodium chloride solution was added to the reaction mixture, then it was extracted with ethyl acetate. The ethyl acetate solution was dried over sodium sulfate and then the drying agent was filtered off. This solution was used without further characterization.

Workup

  1. stirringThe mixture was stirred for additional 1 hour at 0° C
  2. extractionit was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  4. filtrationthe drying agent was filtered off

Sources & evidence

ORD record
ord-e5dee81853ee42bda659ca400c08dfd7
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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