Dichloromethane → HCID 178467736, compound

HRID 2290009Notes

Reaction equation

HRID 2290009 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16](/[CH:21]=[CH:22]/[C:23](=[O:25])[CH3:24])=[CH:15][C:14]=3[F:26])=[O:9])=[CH:4][CH:3]=1.CCN(CC)CC.C(Cl)Cl>[Pd].CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][CH2:22][C:23](=[O:25])[CH3:24])=[CH:15][C:14]=3[F:26])=[O:9])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 178467735HCID 178467735, compound

Product 1

HCID 178467736HCID 178467736, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 887MethanolSolvent

Procedure

To a mixture of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-[(E)-3-oxo-1-butenyl]-3-quinolinecarboxamide from Example No. 153 (100 mg) and Et3N (0.35 mL) in 80 mL 3:1 CH2Cl2 :MeOH is added Pd/C (10%, 20 mg). The reaction mixture is placed under the Parr hydrogenator at 29 psi H2 and monitored by mass spectroscopy for complete reduction of the alkene. The old palladium catalyst is replaced with fresh palladium catalyst each time the reaction was taken off the Parr. In this case, the reaction is taken off the Parr once. The reaction is complete in 45 min. The reaction mixutre is filtered over celite to remove the palladium. The filtrate is concentrated. The crude mixture was separated by HPLC to afford 38.7 mg (8%) of the title compound as a yellow solid.

Workup

  1. filtrationThe reaction mixutre is filtered over celite
  2. customto remove the palladium
  3. concentrationThe filtrate is concentrated
  4. customThe crude mixture was separated by HPLC

Sources & evidence

ORD record
ord-9a612d06e8984fc18d1334eb3448620d
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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