Reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][N:11]2[CH:14]=[C:15]([C:17]3[C:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:19][O:20][C:21]=3[CH3:22])[N:16]=[C:10]2[CH:9]=1)(C)(C)C>Cl>[CH3:22][C:21]1[O:20][N:19]=[C:18]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]=1[C:15]1[N:16]=[C:10]2[CH:9]=[C:8]([NH2:7])[CH:13]=[CH:12][N:11]2[CH:14]=1Participants
3
Procedure
A mixture of [2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-yl]-carbamic acid tert-butyl ester (1.0 g, 2.56 mmol) in hydrochloric acid (4 M in dioxane, 29 mL) was stirred at room temperature for 6 h. The precipitate was then filtered off and dissolved in a dilute solution of sodium hydrogen carbonate and then extracted with ethyl acetate. The organic layer was then washed with brine and then dried over sodium sulphate and evaporated to leave a brown foam. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 25:75) afforded the title compound (477 mg, 64%) which was obtained as a light brown foam. MS: m/e=291.1 [M+H]+.
Workup
- filtrationThe precipitate was then filtered off
- dissolutiondissolved in a dilute solution of sodium hydrogen carbonate
- extractionextracted with ethyl acetate
- washThe organic layer was then washed with brine
- dry with materialdried over sodium sulphate
- customevaporated
- customto leave a brown foam
- customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 25:75)
Sources & evidence
- ORD record
- ord-635211d1d1f6425c87c91612da78fa5f
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07585874B2
Linked notes
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