Sodium Hydroxide → N-benzyl-4-(benzylamino)-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide

HRID 1663473Notes

Reaction equation

[CH2:1]([N:8]1C(=O)[O:11][N:10]=[C:9]1[C:14]1[C:18]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:17][O:16][N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[CH2:1]([NH:8][C:9]([C:14]1[C:18]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:17][O:16][N:15]=1)=[N:10][OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4-benzyl-3-[4-(benzylamino)-1,2,5-oxadiazol-3-yl]-1,2,4-oxadiazol-5(4H)-one (12 mg, 34 μmol) in ethanol (1 mL) was treated with 2 M sodium hydroxide in water (300 μL) and stirred at 25° C. for 30 min. The reaction mixture was quenched with acetic acid and purified by preparative HPLC to give the desired product (10 mg, 90%) as a white solid. LCMS for C17H18N5O2 (M+H)+: m/z=324.2.

Workup

customThe reaction mixture was quenched with acetic acid
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-651d5817e2024b7583bcb87dc4a31866
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034953B2

Reaction notes

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