Water → Ethyl 3-(6-aminopyridin-3-yl)-2-(1-but-2-ynyl-1H-imidazol-4-yl)propionate

HRID 2370941Notes

Reaction equation

HRID 2370941 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH:11]([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.Br[CH2:23][C:24]#[C:25][CH3:26].O>CN(C=O)C>[NH2:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH:11]([C:17]2[N:18]=[CH:19][N:20]([CH2:23][C:24]#[C:25][CH3:26])[CH:21]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27568621-Bromo-2-butyneHCID 178470993HCID 178470993, compound

Product 1

HCID 69331513Ethyl 3-(6-aminopyridin-3-yl)-2-(1-but-2-ynyl-1H-imidazol-4-yl)propionateYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11 mg (0.23 mmol, 50%) of sodium hydride were added to a solution of 60 mg (0.23 mmol) of ethyl 3-(6-aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propionate (example 1g) in 0.5 ml of DMF at RT and stirred for 1 h. Then 31 mg (37 μl, 0.23 mmol) of 1-bromo-2-butine were added, and the mixture was stirred at RT for 1 h. 1 ml of water was then added and the mixture was extracted with EA. The organic phase was dried over Na2SO4, filtered and concentrated. Chromatography of the residue on silica gel afforded 28 mg of the title compound.

Workup

  1. stirringthe mixture was stirred at RT for 1 h
  2. extractionthe mixture was extracted with EA
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-df2fdcbaa70d4f1c8ed1c6542051fd19
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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