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

HRID 612106Notes

Reaction equation

HRID 612106 reaction equation
[CH2:1]([N:4]([CH2:11][CH2:12][CH3:13])[CH2:5][C:6]#[C:7][C:8]([OH:10])=O)[CH2:2][CH3:3].CN1CCOCC1.[NH2:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]=[CH:27][C:26]([C:32]#[N:33])=[C:25]2[NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([Br:41])[CH:36]=1>C1COCC1.N1C=CC=CC=1>[Br:41][C:37]1[CH:36]=[C:35]([NH:34][C:25]2[C:24]3[C:29](=[CH:30][CH:31]=[C:22]([NH:21][C:8](=[O:10])[C:7]#[C:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:11][CH2:12][CH3:13])[CH:23]=3)[N:28]=[CH:27][C:26]=2[C:32]#[N:33])[CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrileHCID 117898744-Dipropylamino-2-butynoic acid

Product 1

HCID 11733863N-{4-[(3-Bromophenyl)amino]-3-cyano-6-quinolinyl}-4-dipropylamino-2-butynamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Partially dissolved 1.28 g (7.0 mmol) 4-dipropylamino-2-butynoic acid in 100 ml THF and chilled to 0° C. under N2. Added 974 μl (8.85 mmol) N-methylmorpholine 768 μl (5.90 mmol) isobutyl chloroformate and stirred for 30 minutes. Added a solution of 1.00 g (2.95 mmol) ) 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile in 8 ml pyridine. At two hours, quenched with ice water and extracted with ethyl acetate. Dried organic layer with magnesium sulfate, reduced solvent to a small volume and loaded onto a column of silica gel. Eluted with ethyl acetate, stripped solvent from desired fractions and dried in vacuo, giving 764 mg of yellow solid: mass spectrum (electrospray m/e): M+H=504, 506.4.

Workup

  1. waitAt two hours
  2. customquenched with ice water
  3. extractionextracted with ethyl acetate
  4. washEluted with ethyl acetate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8e673168a23849079a17fb2e623a0d07
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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