Water → HCID 21192546, compound

HRID 1067966Notes

Reaction equation

HRID 1067966 reaction equation
[Cl:1]C1C=CC(C[C:7]2[C:16]([C:17]([NH2:19])=[O:18])=[C:15]([OH:20])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:21]#[C:22][CH2:23][OH:24])[CH:13]=3)[N:8]=2)=CC=1.C([O-])([O-])=O.[K+].[K+].[ClH:33].[CH:34]([N:37]([CH2:41][CH2:42]Cl)[CH:38](C)C)(C)C.O>CN(C=O)C>[ClH:1].[Cl:33][C:9]1[CH:14]=[CH:13][C:12]([CH2:21][NH:19][C:17]([C:16]2[C:15](=[O:20])[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:21]#[C:22][CH2:23][OH:24])[CH:13]=3)[N:8]([CH2:42][CH2:41][N:37]([CH3:34])[CH3:38])[CH:7]=2)=[O:18])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 178513550HCID 178513550, compound

Product 1

HCID 21192546HCID 21192546, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A solution of N-(4-chlorobenzyl-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 5 (0.515 g) is dissolved in DMF (10 mL), and K2CO3 (0.778 g) and diisoproplyaminoethyl chloride-hydrochloride (0.56 g) are added. The reaction mixture is heated to 95° C. for 14 h, then allowed to stir at room temperature overnight. The mixture is then poured into H2O and an oil formed, which is isolated by decanting the liquid. The oil is dissolved in MeOH/CH2Cl2, and etheral HCl is added to adjust the pH to 2. The mixture is concentrated in vacuo to give the title compound as the hydrochloride salt.

Workup

  1. customan oil formed
  2. customwhich is isolated
  3. customby decanting the liquid
  4. dissolutionThe oil is dissolved in MeOH/CH2Cl2
  5. additionetheral HCl is added
  6. concentrationThe mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-805ea6fc2fd9447aadc91b510c25b6a3
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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