Hydrochloric Acid → 1-(3-Methyl-1,2,4-oxadiazol-5-yl)cyclopropanamine hydrochloride
Reaction equation
C(OC(=O)[NH:7][C:8]1([C:11]2[O:15][N:14]=[C:13]([CH3:16])[N:12]=2)[CH2:10][CH2:9]1)(C)(C)C.O1CCOCC1.[ClH:24]>>[ClH:24].[CH3:16][C:13]1[N:12]=[C:11]([C:8]2([NH2:7])[CH2:10][CH2:9]2)[O:15][N:14]=1Participants
Procedure
To a solution of N-boc-amino-cyclopropanecarboxylic acid (1.01 g, 5.00 mmol) in 2 mL of DMF was added carbonyldiimidazole (0.812 g, 5.01 mmol). This reaction mixture was stirred at room temperature for 6 h. N-Hydroxy-acetamidine (0.374 g, 5.05 mmol) was added. This reaction mixture was stirred at room temperature for 2 h then heated at 100° C. for 16 h. After cooling to room temperature, the reaction mixture was diluted with water. The resultant precipitate was collected by filtration was washed with acetonitrile and water, air-dried to give [1-(3-methyl-1,2,4-oxadiazol-5-yl)-cyclopropyl]-carbamic acid tert-butyl ester as 1.05 g of white solid, m/z 240 [M+1]+. [1-(3-Methyl-1,2,4-oxadiazol-5-yl)-cyclopropyl]-carbamic acid tert-butyl ester (80 mg, 0.33 mmol) was dissolved in HCl in 1,4-dioxane (4.0 M, 1.0 mL, 4.0 mmol). After standing at room temperature for 1 h, the solvent was removed by a stream of nitrogen. The title compound was isolated and used without further purification.
Workup
- customthe solvent was removed by a stream of nitrogen
Sources & evidence
- ORD record
- ord-6faf27d222514470be8c6fc6afbc1307
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552205B2
Reaction notes
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