Water → 2-(3-{2-[1-(Chloroacetyl)piperidin-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,2-oxazol-5-yl)phenyl methanesulphonate
Reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl-].[CH3:7][S:8]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[O:22][N:21]=[C:20]([C:23]2[N:24]=[C:25]([CH:28]3[CH2:33][CH2:32][NH2+:31][CH2:30][CH2:29]3)[S:26][CH:27]=2)[CH2:19]1)(=[O:10])=[O:9].C(N(CC)CC)C.O>ClCCl>[CH3:7][S:8]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]1[O:22][N:21]=[C:20]([C:23]2[N:24]=[C:25]([CH:28]3[CH2:33][CH2:32][N:31]([C:3](=[O:4])[CH2:2][Cl:1])[CH2:30][CH2:29]3)[S:26][CH:27]=2)[CH2:19]1)(=[O:9])=[O:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of chloroacetyl chloride (22 mg) was added, at 0° C., a solution of 4-[4-(5-{2-[(methylsulphonyl)oxy]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidinium chloride (87 mg) and triethylamine (41 mg) in dichloromethane (1 ml). The reaction mixture was stirred at 0° C. for 15 minutes, and at room temperature for a further 18 hours. Then water was added thereto, and the aqueous phase was removed and extracted with dichloromethane. The combined organic phases were dried over magnesium sulphate and concentrated. Purification by column chromatography gave 2-(3-{2-[1-(chloroacetyl)piperidin-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,2-oxazol-5-yl)phenyl methanesulphonate (60 mg, 60%).
Workup
- waitat room temperature for a further 18 hours
- customthe aqueous phase was removed
- extractionextracted with dichloromethane
- dry with materialThe combined organic phases were dried over magnesium sulphate
- concentrationconcentrated
- customPurification by column chromatography
Sources & evidence
- ORD record
- ord-4f35be52a15048f28b13601def05b890
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09375009B2
Reaction notes
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