HCID 178503675, compound → HCID 178503676, compound

HRID 2289986Notes

Reaction equation

HRID 2289986 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([C:23]#[C:24][CH2:25][S:26][CH3:27])=[CH:17][C:16]=3[F:28])=[O:11])=[CH:4][CH:3]=1>[Pd].C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([CH2:23][CH2:24][CH2:25][S:26][CH3:27])=[CH:17][C:16]=3[F:28])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 178503675HCID 178503675, compound

Product 1

HCID 178503676HCID 178503676, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of N-[(4-Chlorophenyl)methyl]-8-fluoro-4-hydroxy-6-[3-(methylthio)-1-propynyl]-3-quinolinecarboxamide from Example No. 126 (0.07 g) and Pd/C (10%, 0.120 g) in 3:1 CH2Cl2 /MeOH (20 mL) was placed on a Parr hydrogenator under 45 psi of H2 and shaken for 4 h. Another 0.08 g of Pd/C was added, and the resulting mixture is shaken for 2 h. The reaction mixture is then filtered through Celite, 0.120 g of fresh catalyst was added, and the resulting mixture was shaken under H2 for 6 h. The reaction mixture is then filtered through Celite and concentrated in vacuo. Crystallization from EtOH gave 0.015 g of the title compound as a solid.

Workup

  1. stirringthe resulting mixture is shaken for 2 h
  2. filtrationThe reaction mixture is then filtered through Celite, 0.120 g of fresh catalyst
  3. additionwas added
  4. stirringthe resulting mixture was shaken under H2 for 6 h
  5. filtrationThe reaction mixture is then filtered through Celite
  6. concentrationconcentrated in vacuo
  7. customCrystallization from EtOH

Sources & evidence

ORD record
ord-79322000ccb44a4d832e1244da03d9d4
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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