(+)-1,4-Dihydro-5-isopropoxy-2-methyl-4-(2-trifluoromethylphenyl)-1,6-naphthyridine-3-carboxylic acid benzyl ester → (+)-1,4-Dihydro-5-isopropoxy-2-methyl-4-(2-trifluoromethylphenyl)-1,6-naphthyridine-3-carboxylic acid

HRID 2248145

Reaction equation

HRID 2248145 reaction equation
C([O:8][C:9]([C:11]1[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])[C:19]2[C:14](=[CH:15][CH:16]=[N:17][C:18]=2[O:31][CH:32]([CH3:34])[CH3:33])[NH:13][C:12]=1[CH3:35])=[O:10])C1C=CC=CC=1>C(O)C.[Pd]>[CH:32]([O:31][C:18]1[N:17]=[CH:16][CH:15]=[C:14]2[C:19]=1[CH:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([F:29])([F:30])[F:28])[C:11]([C:9]([OH:10])=[O:8])=[C:12]([CH3:35])[NH:13]2)([CH3:34])[CH3:33]

Participants

4

Reactant 1

HCID 13923228(+)-1,4-Dihydro-5-isopropoxy-2-methyl-4-(2-trifluoromethylphenyl)-1,6-naphthyridine-3-carboxylic acid benzyl ester

Product 1

HCID 13670941(+)-1,4-Dihydro-5-isopropoxy-2-methyl-4-(2-trifluoromethylphenyl)-1,6-naphthyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.6 g (0.00331 mole) (+)-1,4-dihydro-5-isopropoxy-2-methyl-4-(2-trifluoromethylphenyl)-1,6-naphthyridine-3-carboxylic acid benzyl ester is taken up in 32 mL ethanol and hydrogenated without the use of pressure at 20° C. in the presence of 0.64 g 10% palladium/charcoal (50% moist). The catalyst is filtered off and the filtrate evaporated to dryness at 35° C. on a rotary evaporator. The solid residue is recrystallized from 10 mL diisopropyl ether. The product is dried at 40° C. in a vacuum drying cabinet; yield: 1.04 g (80.3% of theory).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate evaporated to dryness at 35° C. on a rotary evaporator
  3. customThe solid residue is recrystallized from 10 mL diisopropyl ether
  4. customThe product is dried at 40° C. in a vacuum
  5. customdrying cabinet

Sources & evidence

ORD record
ord-343b204245df41179317667a1a247851
Source dataset
uspto-grants-1991_08
Patent number
US05037987

Linked notes

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