5-Fluoro-2-hydroxypyridine → 4-((2,2-Dimethylpropyl){2-[(5-fluoro-2-pyridinyl)oxy]ethyl}amino)-2-(trifluoromethyl)benzonitrile

HRID 1173467Notes

Reaction equation

HRID 1173467 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][N:4]([CH2:17][CH2:18][OH: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.[F:22][C:23]1[CH:24]=[CH:25][C:26](=O)[NH:27][CH:28]=1>>[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][N:4]([CH2:17][CH2:18][O:19][C:26]1[CH:25]=[CH:24][C:23]([F:22])=[CH:28][N:27]=1)[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:14])([F:15])[F:16])[CH:6]=1

Participants

3

Reactant 2

HCID 27628645-Fluoro-2-hydroxypyridineHCID 68495138HCID 68495138, compound

Product 1

HCID 116755954-((2,2-Dimethylpropyl){2-[(5-fluoro-2-pyridinyl)oxy]ethyl}amino)-2-(trifluoromethyl)benzonitrile

Procedure

Synthesized as described in Example 27B from 4-[(2,2-dimethylpropyl)(2-hydroxyethyl)amino]-2-(trifluoromethyl)benzonitrile (Example 61C) and 5-fluoro-2(1H)-pyridinone: 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J=3.0 Hz, 1H), 7.55 (d, J=8.8 Hz, 1H), 7.35 (m, 1H), 7.27 (d, J=2.7 Hz, 1H; partially obscured by solvent), 6.96-(dd, J=9.0, 2.7 Hz, 1H), 6.66 (ddd, J=9.1, 3.6, 0.6 Hz, 1H), 4.41 (t, J=6.7 Hz, 2H), 3.87 (t, J=6.7 Hz, 2H), 3.33 (s, 2H), 1.00 (s, 9H).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-98dcde38756d4c5191f8046a3b5c40ea
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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