2,2-Dimethyl-1,3-dioxane-4,6-dione → 2,2-Dimethyl-5-[(2-propyl-thiazol-5-ylamino)-methylene]-[1,3]dioxane-4,6-dione

HRID 607140Notes

Reaction equation

HRID 607140 reaction equation
[CH2:1]([C:4]1[S:5][C:6]([NH2:9])=[CH:7][N:8]=1)[CH2:2][CH3:3].[CH3:10][C:11]1([CH3:19])[O:18][C:16](=[O:17])[CH2:15][C:13](=[O:14])[O:12]1.[CH2:20](OC(OCC)OCC)C>C(O)C>[CH3:10][C:11]1([CH3:19])[O:18][C:16](=[O:17])[C:15](=[CH:20][NH:9][C:6]2[S:5][C:4]([CH2:1][CH2:2][CH3:3])=[N:8][CH:7]=2)[C:13](=[O:14])[O:12]1

Participants

5

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformateHCID 451217592-Propylthiazol-5-amine

Product 1

HCID 668083152,2-Dimethyl-5-[(2-propyl-thiazol-5-ylamino)-methylene]-[1,3]dioxane-4,6-dioneYield 54.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Example 5D (212.7 mg, 1.496 mmol) in anhydrous ethanol (5 mL) was treated with Meldrum's acid (237 mg, 1.645 mmol) and triethylorthoformate (0.25 mL, 1.496 mmol) at room temperature, and the reaction was heated in a preheated 100° oil bath. After 15 minutes, the reaction was cooled to room temperature and the solvent removed by rotary evaporation under vacuum. Purification by silica gel flash chromatography with a gradient of 10% to 20% ethyl acetate/methylene chloride afforded the title compound as an off-white solid (240 mg, 0.8099 mmol, 54%).

Workup

  1. temperaturethe reaction was heated in a preheated 100° oil bath
  2. customthe solvent removed by rotary evaporation under vacuum
  3. customPurification by silica gel flash chromatography with a gradient of 10% to 20% ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-8753127df3b74e789c268af80d8e41d7
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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