HCID 9909399, compound → HCID 69760268, compound

HRID 612121Notes

Reaction equation

HRID 612121 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH:20][C:21](=[O:27])[C:22]#[C:23][CH2:24][O:25][CH3:26])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:28]#[N:29])[CH:5]=[CH:6][C:7]=1[F:8]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH:20][C:21](=[O:27])/[CH:22]=[CH:23]\[CH2:24][O:25][CH3:26])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:28]#[N:29])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 1

HCID 9909399HCID 9909399, compound

Product 1

HCID 69760268HCID 69760268, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.05 g (0.1 18 mmol) N-[4[(3-chloro-4-fluorophenyl)amino]-3-cyano-6-quinolinyl]-4-methoxy-2-butynamide and 6 mg of Lindlar catalyst in 15 mL of methanol was hydrogenated at room temperature for 5.5 hrs. The mixture was filtered through a pad of Celite. The solvent was removed to give 0.05 g (99.7%) yellow solid; HRMS m/z 410.0928 (M+.).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-f3fb10f92c854ce3926796b8cf953350
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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