Hydrochloride methanol → HCID 57393951, compound

HRID 2380020Notes

Reaction equation

HRID 2380020 reaction equation
[ClH:1].CO.[CH3:4][O:5][C:6]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][C:7]=1[CH2:8][NH:9][C:10]1[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:12][CH:13]=[CH:14][CH:15]=1.[H][H]>[Pt]>[ClH:1].[CH3:4][O:5][C:6]1[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:28])[F:29])=[CH:22][C:7]=1[CH2:8][NH:9][C@H:10]1[CH2:15][CH2:14][CH2:13][NH:12][C@H:11]1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 21893726Hydrochloride methanolHCID 22918525HCID 22918525, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57393951HCID 57393951, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

To a 250 mL Parr bottle were charged 5.1 gms 5% Pt/C, 85 mL 1.0M HCl/CH3OH, and 1.7 grams of 3-(2-methoxy-5-trifluoromethoxybenzylamino)-2-phenylpyridine. The reaction mixture was hydrogenated at 46-50 psi hydrogen at ambient temperature for 9.5 hours. After filtering the reaction mixture over Celite® and washing the cake with methanol, the filtrate was concentrated to a white solid. This material was repulped in acetonitrile at ambient temperature, filtered, and dried to yield 0.52 grams (25.2%) of a white material. The identity of this material was establishd by high resolution NMR.

Workup

  1. filtrationAfter filtering the reaction mixture over Celite®
  2. washwashing the cake with methanol
  3. concentrationthe filtrate was concentrated to a white solid
  4. customwas repulped in acetonitrile at ambient temperature
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-f7b544709eb24e07942b36b45e53540f
Source dataset
uspto-grants-1994_11
Patent number
US05364943

Reaction notes

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