Potassium Carbonate → HCID 54329645, compound

HRID 1067960Notes

Reaction equation

HRID 1067960 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH:21]=[CH:22][CH2:23][OH:24])[CH:17]=3)[NH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH:21]=[CH:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH2:35][CH2:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)[CH:11]=2)=[O:9])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 54392004HCID 54392004, compound

Product 1

HCID 54329645HCID 54329645, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-(4-chlorobenzyl)-1,4-dihydro-6-[3-hydroxy-1-propenyl]-4-oxo-3-quinolinecarboxamide from Preparations No. 11 and 12 (0.52 g) is dissolved in DMF (4 mL), and potassium carbonate (0.78 g) and N-(2-chloroethyl)morpholine hydrochloride (0.52 g) are added. The mixture is heated at 90° C. for 2 h and then partitioned between water and chloroform. The organic layer is concentrated in vacuo to give a brown oil. Column chromatography (elution with 1-7% MeOH/CHCl3) followed by crystallization from EtOAc/hexane gave the title compound as a mixture of isomers. The mixture is then purified by HPLC chromatography on a 0.46×25 cm Chiralcel OD-H column eluting with EtOH at a rate of 0.5 mL/min. This gave 0.161 g of the alkene mixture as approximately a 2:1 mixture of the trans:cis isomers, which is crystallized from ethyl acetate to give 0.13 g of the title compound as a hydrate.

Workup

  1. custompartitioned between water and chloroform
  2. concentrationThe organic layer is concentrated in vacuo
  3. customto give a brown oil
  4. washColumn chromatography (elution with 1-7% MeOH/CHCl3)
  5. customfollowed by crystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-4e1c462e36f346d48a56daf78a451392
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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