5-((5-Methylpyridin-2-yl)methoxy)-2-nitro-N-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)aniline → 5-((5-methylpyridin-2-yl)methoxy)-N1-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)benzene-1,2-diamine

HRID 1848749Notes

Reaction equation

HRID 1848749 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([N+:34]([O-])=O)=[C:14]([CH:33]=2)[NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)=[N:6][CH:7]=1>[Pt].C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:33]=[C:14]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:25][CH:24]=4)=[CH:19][CH:18]=3)[C:13]([NH2:34])=[CH:12][CH:11]=2)=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 904104425-((5-Methylpyridin-2-yl)methoxy)-2-nitro-N-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)aniline

Product 1

HCID 904113575-((5-methylpyridin-2-yl)methoxy)-N1-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)benzene-1,2-diamineYield 97.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a high pressure reactor were added 5-((5-methylpyridin-2-yl)methoxy)-2-nitro-N-((4′-(trifluoromethyl)-[1,1′-biphenyl]-4-yl)methyl)aniline (147 g, 297 mmol), 5% Pt/C (23.2 g, 2.97 mmol), and THF (2.5 L). The reactor was flushed with nitrogen and then stirred under an atmosphere of H2 (135 psi) for 24 h. The mixture was then filtered through celite and the filtrate was concentrated to dryness to afford the title compound as a tan solid (134 g, 97%). MS (ESI): mass calcd. for C27H24F3N3O, 463.2; m/z found, 464.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.42-8.35 (m, 1H), 7.69 (s, 4H), 7.60-7.53 (m, 2H), 7.50-7.44 (m, 3H), 7.37 (d, J=8.0, 1H), 6.66 (d, J=8.3, 1H), 6.38 (d, J=2.7, 1H), 6.27 (dd, J=8.3, 2.7, 1H), 5.08 (s, 2H), 4.36 (s, 2H), 4.13 (bs, 1H), 3.05 (bs, 2H), 2.30 (s, 3H).

Workup

  1. customThe reactor was flushed with nitrogen
  2. filtrationThe mixture was then filtered through celite
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-fdaff57e61af4de3877ade11c198a8b0
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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