Water → HCID 16073839, compound

HRID 1067971Notes

Reaction equation

HRID 1067971 reaction equation
ClC1C=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].Cl[CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.O>CN(C=O)C>[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]([CH2:35][CH2:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[CH:7]=2)=[O:18])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178513550HCID 178513550, compound

Product 1

HCID 16073839HCID 16073839, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of N-(4-chlorobenzyl-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 5 (0.458 g) is dissolved in DMF (10 mL), and K2CO3 (0.69 g) and 4-(2-chloroethyl)morpholine hydrochloride (0.47 g) are added. The reaction mixture is heated to 90° C. for 2 h. Water is added and a dark solid formed, which is isolated by decanting the liquid. Column chromatography (elution with 1-5% MeOH/CHCl3) gave 0.183 g of a solid. Crystallization by dissolving in CH2Cl2 with a few drops of MeOH and adding to a 1:1 solution of pentane/Et2O gave 0.13 g of the title compound as a solid.

Workup

  1. customa dark solid formed
  2. customwhich is isolated
  3. customby decanting the liquid
  4. washColumn chromatography (elution with 1-5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-4fe527296de549aa91c1b1e371008db3
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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