Potassium Carbonate → N'-hydroxy-2-{2-[(2R)-2-methylpyrrolidin-1-yl]ethyl}-1-benzofuran-5-carboximidamide

HRID 494847Notes

Reaction equation

[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:12]=2[CH:13]=1.Cl.[NH2:21][OH:22].C(=O)([O-])[O-].[K+].[K+]>CCO>[OH:22][N:21]=[C:18]([C:15]1[CH:16]=[CH:17][C:11]2[O:10][C:9]([CH2:8][CH2:7][N:3]3[CH2:4][CH2:5][CH2:6][C@H:2]3[CH3:1])=[CH:13][C:12]=2[CH:14]=1)[NH2:19]

Participants

Conditions

Temperature: 95 °C

Procedure

The product from Example 87B (2.5 g, 9.83 mmol) in EtOH (200 mL) was stirred at 25° C. for 10 minutes. The mixture was treated with hydroxylamine hydrochloride (1.71 g, 24.6 mmol) and potassium carbonate (4.49 g, 32.48 mmol) and the resulting mixture was heated at 95° C. for 16 h with stirring. The reaction mixture was subsequently cooled, filtered through celite, and concentrated under reduced pressure. The crude product was purified with flash chromatography to provide the title compound (1.43 g, 51% yield). MS (ESI) m/e 288 (M+H)+.

Workup

temperatureThe reaction mixture was subsequently cooled
filtrationfiltered through celite
concentrationconcentrated under reduced pressure
customThe crude product was purified with flash chromatography

Sources & evidence

ORD record: ord-7e4e31cb67bc4917b94ecdedf4ff3f9f
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538138B2

Reaction notes

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