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

HRID 1935003Notes

Reaction equation

HRID 1935003 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-847adcd63be748c390ffa89ddb8241f9
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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