Tetrahydrofuran → N-{4-[(4-Bromophenyl)amino]-3-cyano-6-quinolinyl}-2-propenamide

HRID 612088Notes

Reaction equation

HRID 612088 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1.[CH2:22]1C[O:25][CH2:24][CH2:23]1.C(N(CC)CC)C.C(Cl)(=O)C=C>CN(C=O)C.C(=O)(O)[O-].[Na+]>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:24](=[O:25])[CH:23]=[CH2:22])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 224665976-Amino-4-[(4-bromophenyl)amino]-3-quinolinecarbonitrile

Product 1

HCID 22466557N-{4-[(4-Bromophenyl)amino]-3-cyano-6-quinolinyl}-2-propenamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved 500 mg (1.47 mmol) 6-amino-4-[(4-bromophenyl)amino]-3-quinolinecarbonitrile in 1 ml hot DMF, added 6 ml THF and chilled to 0° C. under N2. Added 226 μl (1.62 mmol) triethylamine and 135 μl (1.62 mmol) acryloyl chloride. Removed ice bath at 15 minutes. At 1.5 hours, stripped solvent, slurried residue in dilute sodium bicarbonate, collected solids, and dried in vacuo. Boiled solids in ethyl acetate, collected, and dried in vacuo, giving 194 mg of yellow-orange solid: mass spectrum (electrospray m/e): M+H=393.1, 395.1.

Workup

  1. waitAt 1.5 hours
  2. customcollected solids
  3. customdried in vacuo
  4. customcollected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b13e7ce5323e459f8302f7856a5858f5
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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