Dimethyl Sulfoxide → HCID 58546763, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[C:21](Cl)=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(N(CC)CC)C.CS(C)=O>O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[C:21]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
To a mixture of 3-(3-chloro-quinoxalin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (91) (0.16 g, 0.50 mmol) and piperidine (0.085 g, 1.0 mmol) was added triethylamine (0.10 g, 1.0 mmol) and DMSO (3 mL). The solution was heated to 160° C. in microwave for 2 h. Then the mixture was diluted with water (10 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (10 mL) and brine (10 mL), dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (20% to 50% EtOAc in petroleum ether) to give 3-(3-piperidin-1-yl-quinoxalin-2-yl)-azetidine-1-carboxylic acid tert-butyl ester (92) (0.16 g, 0.90 mmol, 90% yield) as a white solid. ESI-MS (M+1): 369 calc. for C21H28N4O2 368.
Workup
- extractionextracted with EtOAc (2×20 mL)
- washThe combined organic extracts were washed with water (10 mL) and brine (10 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- customThe filtrate was evaporated in vacuo
- customthe residue was purified by flash column chromatography on silica gel (20% to 50% EtOAc in petroleum ether)
Sources & evidence
- ORD record
- ord-c83532357a5c454c9c98f58f2374edf6
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08957073B2
Reaction notes
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