N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitro[1,5]naphthyridin-4-amine → N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}[1,5]naphthyridine-3,4-diamine
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][NH:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][N:23]=4)[N:18]=[CH:17][C:16]=3[N+:25]([O-])=O)[O:10][N:9]=2)=[CH:4][CH:3]=1>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][NH:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][N:23]=4)[N:18]=[CH:17][C:16]=3[NH2:25])[O:10][N:9]=2)=[CH:6][CH:7]=1Participants
3
Procedure
A solution of N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-3-nitro[1,5]naphthyridin-4-amine (15.02 g, 41.11 mmol) in hot methanol (4 L) was filtered to remove a solid and then added to a Parr vessel charged with 5% platinum on carbon (1.5 g) that had been purged with nitrogen and wet with methanol (50 mL). The vessel was purged with hydrogen three times and then placed under hydrogen pressure (25 psi, 1.7×105 Pa) for 12 hours. The catalyst was removed by filtration and washed with a mixture of dichloromethane and methanol, and the filtrate was concentrated under reduced pressure to provide 8.3 g of N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}[1,5]naphthyridine-3,4-diamine containing an impurity.
Workup
- customto remove a solid
- additionadded to a Parr vessel
- additioncharged with 5% platinum on carbon (1.5 g) that
- customhad been purged with nitrogen and wet with methanol (50 mL)
- customThe vessel was purged with hydrogen three times
- customfor 12 hours
- customThe catalyst was removed by filtration
- washwashed with a mixture of dichloromethane and methanol
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0bf7b6f436ac4a7b92c11e48fa787e36
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915281B2
Reaction notes
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