4-(2-Tert-butyl-4-nitrothiophene-5-carbonyl)-1-(2-(dimethylamino)ethyl)-3,3-dimethylpiperazin-2-one → 4-(4-Amino-2-tert-butylthiophene-5-carbonyl)-1-(2-(dimethylamino)ethyl)-3,3-dimethylpiperazin-2-one
Reaction equation
[C:1]([C:5]1[S:6][C:7]([C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])[C:17](=[O:26])[C:16]2([CH3:28])[CH3:27])=[O:14])=[C:8]([N+:10]([O-])=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O.O.[Sn](Cl)(Cl)(Cl)Cl>CO>[NH2:10][C:8]1[CH:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[S:6][C:7]=1[C:13]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][N:23]([CH3:24])[CH3:25])[C:17](=[O:26])[C:16]1([CH3:27])[CH3:28])=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 4-(2-tert-butyl-4-nitrothiophene-5-carbonyl)-1-(2-(dimethylamino)ethyl)-3,3-dimethylpiperazin-2-one (0.200 g, 0.49 mmol) and tin chloride dihydrate (0.55 g, 2.4 mmol) dissolved in 4 mL MeOH was stirred at 70° C. overnight. The reaction mixture was cooled down to room temperature, quenched with saturated NaHCO3 (40 mL), and extracted with ethyl acetate. The combined organic layers was dried, the solvent eliminated under vacuum and the residue purified by chromatographic column (silica gel, dichloromethane) to afford 0.090 g of 4-(4-amino-2-tert-butylthiophene-5-carbonyl)-1-(2-(dimethylamino)ethyl)-3,3-dimethylpiperazin-2-one as a tan solid.
Workup
- temperatureThe reaction mixture was cooled down to room temperature
- customquenched with saturated NaHCO3 (40 mL)
- extractionextracted with ethyl acetate
- customThe combined organic layers was dried
- customthe residue purified by chromatographic column (silica gel, dichloromethane)
Sources & evidence
- ORD record
- ord-7e4ea086ffca47e09ae150b11404218a
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741479B2
Reaction notes
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