Sodium hydride → HCID 23498456, compound

HRID 1418041Notes

Reaction equation

HRID 1418041 reaction equation
[H-].[Na+].Br[CH2:4][C:5]([O:7][CH3:8])=[O:6].[Cl:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[C:18]1[N:19]=[C:20]([N:24]([C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][CH:36]=2)[NH:33][CH:32]=[CH:31]3)[CH2:25][CH2:26][CH3:27])[S:21][C:22]=1[CH3:23]>CN(C)C=O>[Cl:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[C:18]1[N:19]=[C:20]([N:24]([C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][CH:36]=2)[N:33]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH:32]=[CH:31]3)[CH2:25][CH2:26][CH3:27])[S:21][C:22]=1[CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 67620600HCID 67620600, compound

Product 1

HCID 23498456HCID 23498456, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.093 g of 55% sodium hydride in oil and then 0.95 ml of methyl bromoacetate are added, at 0° C., to 0.8 g of 4-(2-chloro-4-methoxyphenyl)-5-methyl-2-[N-(indol-5-yl)-N-propylamino]thiazole obtained above (EXAMPLE 7) in solution in 20 ml of dimethylformamide. After stirring for twelve hours at room temperature, the reaction mixture is poured into ice-water. The mixture is extracted with ethyl acetate and the organic phase is washed a number of times with water, dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on a column of silica gel eluted with a 9/1 (v/v) cyclohexane/ethyl acetate mixture. The expected product is isolated in the form of a white solid (Y=95%); M.p.=80° C. 1H NMR (DMSO): 0.84 (t, 3H), 1.51-1.62 (m, 2H), 1.94 (s, 3H), 3.68 (s, 3H), 3.79 (s, 3H), 3.75-3.82 (m, 2H), 5.17 (s, 2H), 6.50 (d, 1H), 6.91-7.58 (m, 7H).

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. washthe organic phase is washed a number of times with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness
  5. customThe residue is purified by chromatography on a column of silica gel
  6. washeluted with a 9/1 (v/v) cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-96f9540e6ca14710ad710836f7972471
Source dataset
uspto-grants-1999_03
Patent number
US05880135

Reaction notes

Loading…