Piridin-4-one → 4-[[2-(4-Pyridinyloxy)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

HRID 1173435Notes

Reaction equation

HRID 1173435 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:17][C:18]([F:21])([F:20])[F:19])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1.[N:22]1[CH:27]=[CH:26][C:25](=O)[CH2:24][CH:23]=1>COCCOC>[N:22]1[CH:27]=[CH:26][C:25]([O:1][CH2:2][CH2:3][N:4]([CH2:17][C:18]([F:19])([F:20])[F:21])[C:5]2[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:15])([F:16])[F:14])[CH:6]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 17984897Piridin-4-oneHCID 866237314-[(2-Hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 114948124-[[2-(4-Pyridinyloxy)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Synthesized as described in Example 1C from 4-[(2-hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile and 4-pyridone, using dry DME as reaction solvent: 1H NMR (400 MHz, CDCl3) δ 8.45 (dd, J=5.0, 1.3 Hz, 2H), 7.68 (d, J=8.8 Hz, 1H), 7.18 (d, J=2.5 Hz, 1H), 7.01 (dd, J=8.7, 2.6 Hz, 1H), 6.77 (dd, J=4.9, 1.3 Hz, 2H), 4.27 (t, J=5.2 Hz, 2H), 4.19 (q, J=8.5 Hz, 2H), 4.04 (t, J=5.3 Hz, 2H).

Workup

  1. customSynthesized
  2. customas reaction solvent

Sources & evidence

ORD record
ord-36a146536e664e0a9a75b96a6d8d8b88
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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