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

HRID 1934902Notes

Reaction equation

HRID 1934902 reaction equation
ClC(OCC(C)C)=O.CN1CCOCC1.[C:16]([OH:21])(=O)[C:17]#[C:18][CH3:19].[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]([Br:42])[CH:37]=1.C(=O)(O)[O-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[Br: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:16](=[O:21])[C:17]#[C:18][CH3:19])[CH:24]=3)[N:29]=[CH:28][C:27]=2[C:33]#[N:34])[CH:41]=[CH:40][CH:39]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 685352-Butynoic acidHCID 516892Sodium BicarbonateHCID 99677126-Amino-4-(3-bromophenylamino)quinoline-3-carbonitrile

Product 1

HCID 9887521N-[4-[(3-Bromophenyl)amino]-3-cyano-6-quinolinyl]butynamideYield 35.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Isobutyl chloroformate (0.788 g, 5.75 mmol) and N-methylmorpholine (0.581 g, 5.75 mmol) were added to an ice cold solution of 0.485 g (5.75 mmol) of 2-butynoic acid in 20 mL of tetrahydrofuran under N2. After stirring for 10 min, a solution of 1.50 g (4.42 mmol) of 6-amino-4-[(3-bromophenyl)amino]-3-quinolinecarbonitrile in 10 mL of tetrahydrofuran was added and the mixture was stirred overnight at 25° C. A second equivalent of preformed mixed anhydride was then added. After 6 h, the reaction was poured into saturated sodium bicarbonate and brine. The product was collected and washed with hot ethyl acetate and ethanol and dried in vacuo to give 0.638 g of yellow solid; mp 283-285° C. (dec).

Workup

  1. stirringthe mixture was stirred overnight at 25° C
  2. additionwas then added
  3. waitAfter 6 h
  4. customThe product was collected
  5. washwashed with hot ethyl acetate and ethanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-62b431b4f4414fe89e0bd4a145eaf880
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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