Diisopropylethylamine → 4-[5-(5-Bromo-furan-2-yl)-[1,3,4]oxadiazol-2-yl]-1,4-diaza-bicyclo[3.2.2]nonane
Reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[NH:4][CH2:3][CH2:2]2.C(S[C:18]1[O:19][C:20]([C:23]2[O:24][C:25]([Br:28])=[CH:26][CH:27]=2)=[N:21][N:22]=1)C1C=CC=CC=1.C(N(CC)C(C)C)(C)C>[OH-].[Na+]>[Br:28][C:25]1[O:24][C:23]([C:20]2[O:19][C:18]([N:4]3[CH:5]4[CH2:8][CH2:9][N:1]([CH2:7][CH2:6]4)[CH2:2][CH2:3]3)=[N:22][N:21]=2)=[CH:27][CH:26]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 1,4-diazabicyclo[3.2.2]nonane (4.05 g, 32.1 mmol), 2-benzylsulfanyl-5-(5-bromo-furan-2-yl)-[1,3,4]oxadiazole (10.3 g, 30.5 mmol) and N,N-diisopropylethylamine (8.29 g, 64.1 mmol) was stirred at 100° C. for 4 hours. Aqueous sodium hydroxide (30 ml, 1 M) was added followed by extraction with chloroform (3×30 ml). The organic phase was dried and evaporated. The crude solid mixture was solved in hot ethyl acetate (100 ml), some red, glue-like impurities where removed by filtration. The filtrate was evaporated and finally the crystalline product was triturated with diethylether. Yield 3.43 g (33%). LC-ESI-HRMS of [M+H]+ shows 339.0453 Da. Calc. 339.045664 Da, dev. −1.1 ppm.
Workup
- extractionfollowed by extraction with chloroform (3×30 ml)
- customThe organic phase was dried
- customevaporated
- customsome red, glue-like impurities where removed by filtration
- customThe filtrate was evaporated
- customfinally the crystalline product was triturated with diethylether
Sources & evidence
- ORD record
- ord-4a2e2a5e7c9442f7a8635e6f44215be9
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372832B2
Reaction notes
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