Hydrochloric Acid → 3-[4-(4-Methane-sulfonylpiperazin-1-yl)pyridyl]-3,8-diazabicyclo[3.2.1]octane
Reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11]([C:16]1[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]3)[CH:19]=[CH:18][N:17]=1)[CH2:12]2)=O)(C)(C)C.Cl.CO>O1CCOCC1>[CH3:31][S:28]([N:25]1[CH2:26][CH2:27][N:22]([C:20]2[CH:19]=[CH:18][N:17]=[C:16]([N:11]3[CH2:12][CH:13]4[NH:8][CH:9]([CH2:15][CH2:14]4)[CH2:10]3)[CH:21]=2)[CH2:23][CH2:24]1)(=[O:29])=[O:30]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-[4-(4-Methanesulfonylpiperazin-1-yl)pyridyl]-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.75 g, 1.66 mmol) is solubilized in 16 ml of dioxane. 4N HCl in dioxane (4.3 ml, 17.5 mmol) is then added, followed by approximately 3 ml of methanol. After stirring for 16 h at ambient temperature, the reaction medium is concentrated, and taken up with water. After extraction with diethyl ether, the pH of the aqueous phase is brought to pH 10 with K2CO3 in the presence of dichloromethane. After extraction with dichloromethane, the organic phase is washed with a saturated aqueous sodium chloride solution, and dried over MgSO4, and then concentrated to dryness. 0.59 g of expected 3-[4-(4-methane-sulfonylpiperazin-1-yl)pyridyl]-3,8-diazabicyclo[3.2.1]octane is obtained, which is subsequently used as it is.
Workup
- concentrationthe reaction medium is concentrated
- extractionAfter extraction with diethyl ether
- extractionAfter extraction with dichloromethane
- washthe organic phase is washed with a saturated aqueous sodium chloride solution
- dry with materialdried over MgSO4
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-2df0e2675781453498a6fb2065307e0d
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08530477B2
Reaction notes
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