1-[2-(2-Hydroxyethoxy)ethyl]piperazine → HCID 57664407, compound
Reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:23]1([NH:26][C:27]([C:29]2[S:42][C:32]3=[N:33][C:34](S(C)=O)=[C:35]([Cl:38])[C:36]([CH3:37])=[C:31]3[C:30]=2[NH2:43])=[O:28])[CH2:25][CH2:24]1>C1COCC1>[CH:23]1([NH:26][C:27]([C:29]2[S:42][C:32]3=[N:33][C:34]([O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]4[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]4)=[C:35]([Cl:38])[C:36]([CH3:37])=[C:31]3[C:30]=2[NH2:43])=[O:28])[CH2:25][CH2:24]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1-[2-(2-hydroxyethoxy)ethyl]piperazine (1.061 g, 6.09 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 80° C. in a sealed tube for 1.5 hours, 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 forms. 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 (0.078 g, 17%). Mass (m/z): 454.2 (M++1), 452.2 (M+−1).
Workup
- temperaturecooled to room temperature
- customquenched by the addition of water (15 ml)
- additionIce is added to the reaction mixture
- stirringwhile stirring
- filtrationThis solid is collected by filtration
- customto dry (60° C. for 16 hours)
Sources & evidence
- ORD record
- ord-02c419dc4fcd4250b5c3dbc0fe1de345
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071776B2
Reaction notes
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