HCID 10296995, compound → HCID 10138383, compound

HRID 1168225Notes

Reaction equation

HRID 1168225 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[C:16]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]#[C:27][CH3:28])=[C:22]([C:29]([F:32])([F:31])[F:30])[CH:21]=3)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:5][CH:4]=1.[H][H]>CO.[Pt]>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]2[C:16]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH3:28])=[C:22]([C:29]([F:32])([F:31])[F:30])[CH:21]=3)=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 10296995HCID 10296995, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10138383HCID 10138383, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-[(6-methoxypyrid-3-yl)methylamino]-N-[4-propynyl-3-(trifluoromethyl)phenyl]-3-pyridinecarboxamide (Example 30; 1.87 g, 4.25 mmol) in methanol (100 mL) is hydrogenated at atmospheric pressure over 5% platinum on carbon (0.4 g) at 22° C. The calculated amount of hydrogen is taken up in 13 hours. The mixture is then filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by recrystallisation from dichloromethane—hexane to give the title compound as a colourless crystalline solid, m.p. 51-61° C.

Workup

  1. filtrationThe mixture is then filtered
  2. customthe solvent is evaporated off under reduced pressure
  3. customto yield the crude product which
  4. customis purified by recrystallisation from dichloromethane—hexane

Sources & evidence

ORD record
ord-fbeb18db8b394aafaed74bf8c402495e
Source dataset
uspto-grants-2003_09
Patent number
US06624174B2

Reaction notes

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