Toluene → N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N2,N2-bis(4-methoxybenzyl)-5,6-dimethylpyridine-2,3,4-triamine

HRID 606090Notes

Reaction equation

HRID 606090 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][NH:21][C:22]3[C:27]([CH3:28])=[C:26]([CH3:29])[N:25]=[C:24]([N:30]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=4)[CH2:31][C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[C:23]=3[N+:49]([O-])=O)[O:17][N:16]=2)=[CH:11][CH:10]=1>[Pt].C(O)C>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][NH:21][C:22]3[C:27]([CH3:28])=[C:26]([CH3:29])[N:25]=[C:24]([N:30]([CH2:31][C:32]4[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=4)[CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=4)[C:23]=3[NH2:49])[O:17][N:16]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 1140TolueneHCID 69450751N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N2,N2-bis(4-methoxybenzyl)-5,6-dimethyl-3-nitropyridin-2,4-diamine

Product 1

HCID 69453189N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N2,N2-bis(4-methoxybenzyl)-5,6-dimethylpyridine-2,3,4-triamineYield 112.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, toluene (2 L) was added to a Parr vessel containing 5% platinum on carbon (3.6 g). N4-{[3-(4-Fluorophenyl)isoxazol-5-yl]methyl}-N2,N2-bis(4-methoxybenzyl)-5,6-dimethyl-3-nitropyridin-2,4-diamine (36.85 g, 61.66 mmol) was added followed by ethanol (300 mL). The vessel was sealed, purged with hydrogen, and placed under hydrogen pressure (30 psi, 2.1×105 Pa) for 18 hours at room temperature. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to provide 39.25 g of N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N2,N2-bis(4-methoxybenzyl)-5,6-dimethylpyridine-2,3,4-triamine as a yellow oil.

Workup

  1. customThe vessel was sealed
  2. custompurged with hydrogen
  3. customfor 18 hours
  4. customat room temperature
  5. customThe catalyst was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1fb28d69c9914565ae7c5ede1f48c1b6
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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