Sodium hydride → HCID 20624493, compound

HRID 2120911Notes

Reaction equation

HRID 2120911 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[S:11][CH:12]=[C:13]([CH2:15][OH:16])[N:14]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[H-].[Na+].CS(O[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)(=O)=O.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1.C(OCC)(=O)C.CCCCCC>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[S:11][CH:12]=[C:13]([CH2:15][O:16][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[N:14]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 11139085[2-(2H-1,3-Benzodioxol-5-yl)-1,3-thiazol-4-yl]methanolHCID 22417657Methanesulfonic acid pyridin-2-ylmethyl ester

Product 1

HCID 20624493HCID 20624493, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

2-(Benzo[3,4-d]1,3-dioxolan-5-yl)-4-hydroxymethyl-1,3-thiazole prepared in Example 20(200 mg, 0.85 mmol) was dissolved in N,N-dimethylformamide(5 ml), and sodium hydride(30.7 mg, 1.28 mmol) was added thereto at 0-5° C. To this mixture was added dropwise 2-(methane sulfonyloxymethyl)pyridine(315 mg) dissolved in 1 ml of tetrahydrofuran, and the resulting mixture was stirred for 2 hours at room temperature. Saturated sodium bicarbonate solution was added to the reaction mixture, which was then extracted with a solvent mixture of ethyl acetate/n-hexane(1/1, v/v). The extract was washed with saturated saline solution, dried over anhydrous sodium sulfate, and concentrated. The concentrate was subjected to silica gel column chromatography(eluent: ethyl acetate/n-hexane=1/2, v/v) to give the title compound(180 mg, Yield 65%) as an ivory solid.

Workup

  1. customat 0-5° C
  2. extractionwas then extracted with a solvent mixture of ethyl acetate/n-hexane(1/1
  3. washThe extract was washed with saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-27c0e2e779cc4d8e8c352be77f57cc65
Source dataset
uspto-grants-2004_02
Patent number
US06693126B2

Reaction notes

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