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

HRID 611979Notes

Reaction equation

HRID 611979 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 tide 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-69730af2d40d468ca31e9e9a3f5672f9
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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