Triethylamine → HCID 68447103, compound

HRID 899956Notes

Reaction equation

HRID 899956 reaction equation
[H-].[Na+].[F:3][C:4]([S:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18](=[O:19])[CH2:17][NH:16][C:15]2=[O:20])=[CH:10][CH:9]=1)([F:6])[F:5].C(N(CC)CC)C.Br.Br[CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>CN(C)C=O.O.C(#N)C>[N:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:16]2[CH2:17][C:18](=[O:19])[N:14]([C:11]3[CH:10]=[CH:9][C:8]([S:7][C:4]([F:3])([F:5])[F:6])=[CH:13][CH:12]=3)[C:15]2=[O:20])=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 127522194-(Bromomethyl)pyridine hbrHCID 132680603-{4-[(Trifluoromethyl)sulfanyl]phenyl}imidazolidine-2,4-dione

Product 1

HCID 68447103HCID 68447103, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent2×

Procedure

0.087 g sodium hydride is added to a solution of 0.300 g of 3-(4-trifluoromethylsulfanylphenyl)imidazolidine-2,4-dione in 6 ml of anhydrous dimethylformamide, under an inert atmosphere of argon at a temperature in the region of 20° C., stirring is continued at this temperature for 30 minutes, 0.152 ml of triethylamine and 0.274 g of 4-(bromomethyl)pyridine hydrobromide are successively added, followed by addition of ice-cold water 10 minutes later. The reaction mixture is placed on a cartridge 37 mm in diameter packed with 50 g of Amicon 50 μm octadecyl-grafted silica of ref. conditioned successively with a water/acetonitrile mixture (5/95, v/v) and then a water/acetonitrile mixture (95/5, v/v). The elution was performed with a water/acetonitrile mixture (95/5, v/v) over 20 minutes, followed by a linear gradient from 5% to 95% of acetonitrile over 60 minutes, at a flow rate of 10 ml/minute. The fractions between 580 and 630 ml are concentrated under reduced pressure. 0.220 g of 1-pyrid-4-ylmethyl-3-(4-trifluoromethylsulfanylphenyl)imidazolidine-2,4-dione is thus obtained in the form of a white powder, the characteristics of which are as follows:

Workup

  1. additionfollowed by addition of ice-cold water 10 minutes later
  2. washThe elution
  3. waitv/v) over 20 minutes
  4. waitfollowed by a linear gradient from 5% to 95% of acetonitrile over 60 minutes, at a flow rate of 10 ml/minute
  5. concentrationThe fractions between 580 and 630 ml are concentrated under reduced pressure

Sources & evidence

ORD record
ord-58bd2c827eec4620b5e0aa4b0d621e27
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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