2-Bromoethanol → HCID 71495248, compound

HRID 588053Notes

Reaction equation

HRID 588053 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:27])[C:10]2[CH:15]=[CH:14][CH:13]=[N:12][C:11]=2[NH:16][CH:17]2[CH2:22][C:21]([CH3:24])([CH3:23])[NH:20][C:19]([CH3:26])([CH3:25])[CH2:18]2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:29][CH2:30][OH:31].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:27])[C:10]2[CH:15]=[CH:14][CH:13]=[N:12][C:11]=2[NH:16][CH:17]2[CH2:22][C:21]([CH3:23])([CH3:24])[N:20]([CH2:29][CH2:30][OH:31])[C:19]([CH3:26])([CH3:25])[CH2:18]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 71496699HCID 71496699, compound

Product 1

HCID 71495248HCID 71495248, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-(3-chlorophenyl)-2-(2,2,6,6-tetramethylpiperidin-4-ylamino)nicotinamide (330 mg, 1 mmol, 1 eq), 2-bromoethanol (1.2 mmol), and anhydrous potassium carbonate (1.2 mmol) in 5 ml of acetonitrile was stirred for 18 hrs under reflux. The reaction mixture was cooled to a room temperature and filtered. The filtrate was concentrated in a reduced pressure. Silica gel column chromatography (mobile phase: 10 (v/v) % methanol in chloroform) afforded the title compound. Yield: 37.1% 1H NMR (CDCl3) δ 8.22 (d, 1H), 7.79 (d, 1H), 7.69 (d, 1H), 7.65 (s, 1H), 7.37 (d, 1H), 7.27 (t, 1H), 7.10 (d, 1H), 6.51-6.45 (m, 1H), 4.64-4.45 (m, 1H), 3.88 (t, 2H), 3.49 (t, 2H), 2.08-1.96 (m, 3H), 1.28 (s, 6H), 1.13 (s, 6H), 1.0 (t, 2H) ppm.

Workup

  1. temperatureunder reflux
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in a reduced pressure

Sources & evidence

ORD record
ord-833a9242dc4c4f768ab59948cd682137
Source dataset
uspto-grants-2016_01
Patent number
US09227955B2

Reaction notes

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