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Diethylene Glycol → 3-Amino-5-chloro-6-[2-(2-hydroxy-ethoxy)-ethoxy]-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

HRID 656650
Notes
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Reaction equation

HRID 656650 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]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 2733832Lithium hexamethyldisilazaneHCID 576644203-Amino-5-chloro-6-methanesulfinyl-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

Product 1

HCID 576644173-Amino-5-chloro-6-[2-(2-hydroxy-ethoxy)-ethoxy]-4-methyl-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamideYield 39%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

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

  1. temperaturecooled to room temperature
  2. customquenched by the addition of water (15 ml)
  3. additionIce is added to the reaction mixture
  4. stirringwhile stirring
  5. customa yellow precipitate is formed
  6. filtrationThis solid is collected by filtration
  7. customto dry (60° C. for 16 hours)

Sources & evidence

ORD record
ord-014eeb49760a484c8dd708f60d857bb0
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08071776B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes