HCID 178477427, compound → HCID 178477426, compound

HRID 2289985Notes

Reaction equation

HRID 2289985 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][CH2:27][CH3:28])=[CH:17][C:16]=3[F:29])=[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](/[CH:23]=[CH:24]\[CH2:25][S:26][CH2:27][CH3:28])=[CH:17][C:16]=3[F:29])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 178477427HCID 178477427, compound

Product 1

HCID 178477426HCID 178477426, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of N-[(4-Chlorophenyl)methyl]-6-[3-(ethylthio)-1-propynyl]-8-fluoro-4-hydroxy-3-quinolinecarboxamide from Example No. 127 (0.15 g) and Pd/C (10%, 0.06 g) in 3:1 CH2Cl2 /MeOH (20 mL) are placed on a Parr hydrogenator under 40 psi of H2 and shaken for 3 h. The reaction mixture is then filtered through Celite and concentrated in vacuo. Crystallization from MeOH affords the title compound as a solid.

Workup

  1. filtrationThe reaction mixture is then filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customCrystallization from MeOH

Sources & evidence

ORD record
ord-9d138961bbe74847aa941a6d07f8c3d6
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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