4-Methylmorpholine → N-[4-(3-Bromo-phenylamino)-3-cyano-7-methoxy-quinolin-6-yl]-acrylamide

HRID 1934899Notes

Reaction equation

HRID 1934899 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[CH:7][C:6]([C:14]#[N:15])=[C:5]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=1.CN1CCOCC1.[C:31](Cl)(=[O:34])[CH:32]=[CH2:33]>O1CCCC1.C(OCC)(=O)C>[Br:23][C:19]1[CH:18]=[C:17]([NH:16][C:5]2[C:4]3[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:2]([NH:1][C:31](=[O:34])[CH:32]=[CH2:33])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:14]#[N:15])[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 13140Acryloyl chlorideHCID 98206456-Amino-4-[(3-bromophenyl)amino]-7-methoxy-quinoline-3-carbonitrile

Product 1

HCID 10295839N-[4-(3-Bromo-phenylamino)-3-cyano-7-methoxy-quinolin-6-yl]-acrylamideYield 29.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.5 g (4.06 mmol) of 6-Amino-4-[(3-bromophenyl)amino]-7-methoxy-3-quinolinecarbonitrile and 0.45 ml of N-methylmorpholine in 30 ml of tetrahydrofuran was added at 0° C., under nitrogen, with stirring, 0.42 g (4.7 mmol) of acryloyl chloride of a 15 minute period. After 1 hour at 0° C., the solution was diluted with 200 ml ethyl acetate. The mixture was washed with saturated sodium bicarbonate solution and then dried over magnesium sulfate. The solvent was removed. The residue was chromatographed on silica gel eluted with chloroform-ethyl acetate mixtures to give 0.5 g of the title compound as a light yellow solid powder: mass spectrum (electrospray, m/e): M+H 423.1,425.1

Workup

  1. washThe mixture was washed with saturated sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed
  4. customThe residue was chromatographed on silica gel
  5. washeluted with chloroform-ethyl acetate mixtures

Sources & evidence

ORD record
ord-e720d0766474442081611312456798cd
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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