HCID 16073829, compound → HCID 6479235, compound

HRID 1067962Notes

Reaction equation

HRID 1067962 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[C:14]([F:25])[CH:15]=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH3:26])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1>CO.C(Cl)Cl.[Pd]>[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](=[C:14]([F:25])[CH:15]=[C:16](/[CH:21]=[CH:22]\[CH2:23][OH:24])[CH:17]=3)[N:12]([CH3:26])[CH:11]=2)=[O:9])=[CH:27][CH:28]=1

Participants

5

Reactant 1

HCID 16073829HCID 16073829, compound

Product 1

HCID 6479235HCID 6479235, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(4-chlorobenzyl)-8-fluoro-1,4-dihydro-6-(3-hydroxy-1-propynyl)-1-methyl-4-oxo-3-quinolinecarboxamide from Example No. 8 (0.200 g) and Pd/C (10%, 0.040 g) in MeOH (10 mL) and CH2Cl2 (10 mL) is placed on a Parr shaker under 50 psi of H2 for 6 h. The reaction mixture is filtered through Celite and concentrated in vacuo. Recrystallization from EtOAc gave the title compound as a solid.

Workup

  1. filtrationThe reaction mixture is filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customRecrystallization from EtOAc

Sources & evidence

ORD record
ord-ecd326013d24475b9a9ff90bfff17779
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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