3-Methoxypropanoyl chloride → N-[2-Chloro-4-(2-hydroxy-2-methylpropyl)amino-3-quinolinyl]-3-methoxypropanamide

HRID 1699708Notes

Reaction equation

HRID 1699708 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[NH2:8][C:9]1[C:10]([Cl:25])=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][C:21]([CH3:24])([OH:23])[CH3:22])=[CH:16][CH:15]=[CH:14][CH:13]=2>C(#N)C>[Cl:25][C:10]1[C:9]([NH:8][C:5](=[O:6])[CH2:4][CH2:3][O:2][CH3:1])=[C:18]([NH:19][CH2:20][C:21]([OH:23])([CH3:22])[CH3:24])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1

Participants

4

Reactant 2

HCID 27597283-Methoxypropanoyl chlorideHCID 226726541-((3-Amino-2-chloroquinolin-4-yl)amino)-2-methylpropan-2-ol

Product 1

HCID 22672655N-[2-Chloro-4-(2-hydroxy-2-methylpropyl)amino-3-quinolinyl]-3-methoxypropanamideYield 92.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Methoxypropionyl chloride (5.5 g, 0.045 mole) was slowly added with stirring to a solution of 1[(3-amino-2-chloro-4-quinolinyl)amino]-2-methyl-2-propanol (10 g, 0.038 mole) in acetonitrile (140 mL). After the addition was completed, the reaction mixture was heated at reflux for 30 minutes then allowed to stir at room temperature overnight. The reaction mixture was filtered to provide 12.4 g of the desired product as a solid.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 30 minutes
  4. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-aad9bf41b03d4ab8b24f65bce46eb66c
Source dataset
uspto-grants-2002_02
Patent number
US06348462B1

Reaction notes

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