4-Methylmorpholine → N-{4-[(3-Chlorophenyl)amino]-3-cyano-6-quinolinyl]-2-butynamide

HRID 612238Notes

Reaction equation

HRID 612238 reaction equation
[C:1]([OH:6])(=O)[C:2]#[C:3][CH3:4].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][C:27]([C:33]#[N:34])=[C:26]2[NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=1>C1COCC1.CN(C=O)C.O>[Cl:42][C:38]1[CH:37]=[C:36]([NH:35][C:26]2[C:25]3[C:30](=[CH:31][CH:32]=[C:23]([NH:22][C:1](=[O:6])[C:2]#[C:3][CH3:4])[CH:24]=3)[N:29]=[CH:28][C:27]=2[C:33]#[N:34])[CH:41]=[CH:40][CH:39]=1

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 685352-Butynoic acidHCID 224666926-Amino-4-(3-chlorophenylamino)quinoline-3-carbonitrile

Product 1

HCID 22466578N-{4-[(3-Chlorophenyl)amino]-3-cyano-6-quinolinyl]-2-butynamideYield 79.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolved 428 mg (5.09 mmol) 2-butynoic acid in 40 ml THF and chilled to 0° C. under N2. Added 560 μl (5.09 mmol) N-methylmorpholine and 662 μl (5.09 mmol) isobutyl chloroformate and stirred for 10 minutes. Added dropwise a solution of 1.00 g (3.39 mmol) 6-amino-4-[(3-chlorophenyl)amino]-3-quinolinecarbonitrile in 2 ml DMF and 20 ml THF. Removed ice bath at 15 minutes and stirred at 25° C. overnight. Stripped solvent, slurried residue with water and collected solids. Boiled in ethyl acetate, collected and dried in vacuo, giving 975 mg of yellow solid: mass spectrum (electrospray m/e): M+H=361.1, 363.2.

Workup

  1. waitRemoved ice bath at 15 minutes
  2. stirringstirred at 25° C. overnight
  3. customcollected solids
  4. customcollected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ef9e5a62c4684531b1c8138807b0a977
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

Loading…