Diethylene Glycol → 3-Amino-5-chloro-6-[2-(2-hydroxy-ethoxy)-ethoxy]-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide
Reaction equation
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:18]1([NH:21][C:22]([C:24]2[S:37][C:27]3=[N:28][C:29](S(C)=O)=[C:30]([Cl:33])[C:31]([CH3:32])=[C:26]3[C:25]=2[NH2:38])=[O:23])[CH2:20][CH2:19]1>C1COCC1>[CH:18]1([NH:21][C:22]([C:24]2[S:37][C:27]3=[N:28][C:29]([O:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][OH:6])=[C:30]([Cl:33])[C:31]([CH3:32])=[C:26]3[C:25]=2[NH2:38])=[O:23])[CH2:20][CH2:19]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a solution of diethylene glycol (1.118 g, 10.54 mmol) in THF (3 ml) at room temperature is added dropwise a solution of lithium bis(trimethylsilyl)amide (1.0 M in hexanes) (3.50 ml, 3.50 mmol). The reaction mixture is stirred for 15 minutes and then is treated with 3-amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide (0.345 g, 1.00 mmol). The reaction mixture is heated at 75° C. for 1 hour, cooled to room temperature, and then quenched by the addition of water (15 ml). Ice is added to the reaction mixture and, while stirring, a yellow precipitate is formed. This solid is collected by filtration and placed in the vacuum oven to dry (60° C. for 16 hours). This affords the title compound as a yellow solid (0.150 g, 39%). Mass (m/z): 386.2 (M++1), 384.1 (M+−1).
Workup
- temperaturecooled to room temperature
- customquenched by the addition of water (15 ml)
- additionIce is added to the reaction mixture
- stirringwhile stirring
- customa yellow precipitate is formed
- filtrationThis solid is collected by filtration
- customto dry (60° C. for 16 hours)
Sources & evidence
- ORD record
- ord-014eeb49760a484c8dd708f60d857bb0
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071776B2
Reaction notes
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