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

HRID 1934987Notes

Reaction equation

HRID 1934987 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][CH:18]=[C:17]([Cl:21])[CH:16]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:32])[CH:30]=[CH2:31].C(=O)(O)[O-].[Na+]>CN(C=O)C.C1COCC1>[Cl:21][C:17]1[CH:16]=[C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:29](=[O:32])[CH:30]=[CH2:31])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 516892Sodium BicarbonateHCID 224666926-Amino-4-(3-chlorophenylamino)quinoline-3-carbonitrile

Product 1

HCID 22466710N-{4-[(3-Chlorophenyl)amino]-3-cyano-6-quinolinyl}-2-propenamideYield 39.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved 430 mg (1.46 mmol) 6-amino-4-[(3-chlorophenyl)amino]-3-quinolinecarbonitrile in 4 ml DMF, added 10 ml THF and chilled to 0° C. under N2. Added 224 μl (1.60 mmol) triethylamine and 133 μl (1.60 mmol) acryloyl chloride. Removed ice bath at 15 minutes, reaction complete at this time, but stirred overnight at 25° C. Stripped solvent, added a dilute sodium bicarbonate to the residue and collected solids. Washed with water and dried in vacuo. Boiled in ethyl acetate, collected solids and dried in vacuo, giving 200 mg of orange solid: mass spectrum (electrospray m/e): M+H=349.0, 351.0.

Workup

  1. customreaction complete at this time
  2. customcollected solids
  3. washWashed with water
  4. customdried in vacuo
  5. customcollected solids
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1540d67696664484aab19a649d82f719
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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