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 1527771Notes

Reaction equation

HRID 1527771 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-fa1046c8c5ad4afdb19dcf2a5fdd1a88
Source dataset
uspto-grants-2015_07
Patent number
US09089569B2

Reaction notes

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