Ethylene Glycol → 4-({[3,5-Dicyano-6-(2-hydroxyethoxy)-4-phenylpyridin-2-yl]thio}methyl)-N-methylpyridine-2-carboxamide
Reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].Cl[C:8]1[N:13]=[C:12]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH3:25])=[O:23])[CH:17]=2)[C:11]([C:26]#[N:27])=[C:10]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]=1[C:34]#[N:35]>CN(C=O)C>[C:26]([C:11]1[C:12]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH3:25])=[O:23])[CH:17]=2)=[N:13][C:8]([O:3][CH2:2][CH2:1][OH:4])=[C:9]([C:34]#[N:35])[C:10]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)#[N:27]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 115 °C
Procedure
22 mg (0.357 mmol) of 1,2-ethanediol are initially charged in 0.5 ml of DMF, and 4.8 mg (0.179 mmol) of sodium hydride are added. After 15 min at RT, 50 mg (0.119 mmol) of the compound from Example 25A are added and the reaction mixture is stirred at 115° C. overnight. After cooling, the reaction solution is purified by prep. HPLC.
Workup
- temperatureAfter cooling
- customthe reaction solution is purified by prep
Sources & evidence
- ORD record
- ord-fce8e83ad2fc4d2db8801cbaac60ffdf
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09205077B2
Reaction notes
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