Sodium Chloride → HCID 54186400, compound

HRID 612139Notes

Reaction equation

HRID 612139 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([C:14]#[N:15])[CH:10]=[N:11]2)=[CH:6][C:5]=1[NH2:16])[CH3:2].CC[N:19]([CH:23]([CH3:25])[CH3:24])C(C)C.[Br:26][CH2:27]/[CH:28]=[CH:29]/[C:30](Cl)=[O:31].[Cl-].[Na+]>C1COCC1>[Br:26][C:27]1[CH:25]=[C:23]([NH:19][C:8]2[C:7]3[C:12](=[CH:13][C:4]([O:3][CH2:1][CH3:2])=[C:5]([NH:16][C:30](=[O:31])[CH:29]=[CH:28][CH2:27][Br:26])[CH:6]=3)[N:11]=[CH:10][C:9]=2[C:14]#[N:15])[CH:24]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 11263885(E)-4-Bromo-2-butenoyl ChlorideHCID 86754954HCID 86754954, compound

Product 1

HCID 54186400HCID 54186400, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1.34 g (3.5 mmol) of 4-[3-bromo-phenyl)amino]-7-ethoxy-6-amino-3-quinolinecarbonitrile and 3.66 ml (21 mmol) of Hunig's base in 80 ml of dry THF at 0° C., with stirring, was added a THF solution containing 3.85 g (21 mmol) of 4-bromo crotonyl chloride dropwise. The mixture was stirred for additional 30 minutes 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 30 minutes 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-07b88bf206c44015a311b50b461645dd
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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