1,1'-Carbonyldiimidazole → 4-[(4-Bromo-2-furyl)methyl]-3-{4-[(2-methoxyethyl)amino]-1,2,5-oxadiazol-3-yl}-1,2,4-oxadiazol-5(4H)-one

HRID 415849Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][NH:8][C:9]([C:12]2[C:16]([NH:17][CH2:18][CH2:19][O:20][CH3:21])=[N:15][O:14][N:13]=2)=[N:10][OH:11])[O:5][CH:6]=1.[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23]>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][N:8]2[C:22](=[O:23])[O:11][N:10]=[C:9]2[C:12]2[C:16]([NH:17][CH2:18][CH2:19][O:20][CH3:21])=[N:15][O:14][N:13]=2)[O:5][CH:6]=1

Participants

Conditions

Temperature: 65 °C

Procedure

N-[(4-Bromo-2-furyl)methyl]-N′-hydroxy-4-[(2-methoxyethyl)amino]-1,2,5-oxadiazole-3-carboximidamide (7.3 g, 20.4 mmol) and 1,1′-carbonyldiimidazole (5.0 g, 30.5 mmol) were dissolved in ethyl acetate (72 mL). The reaction mixture was heated at 65° C. for 15 minutes. Ethyl acetate (70 mL) was added and the crude reaction was washed with 0.1 N hydrogen chloride in water (2×70 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography on silica gel with an eluent of ethyl acetate in hexanes gave the desired product (4.1 g, 90%). LCMS calculated for C12H13BrN5O5 (M+H)+: m/z=386.0, 388.0. 1H NMR (400 MHz, CD3OD): δ 7.88 (s, 1H), 6.67 (s, 1H), 6.39 (t, J=5.7 Hz, 1H), 5.07 (s, 2H), 3.50 (m, 2H), 3.41 (q, J=5.7 Hz, 2H), 3.25 (s, 3H).

Workup

customthe crude reaction
washwas washed with 0.1 N hydrogen chloride in water (2×70 mL)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customPurification by flash chromatography on silica gel with an eluent of ethyl acetate in hexanes

Sources & evidence

ORD record: ord-5dce4c498e1145f680fe1a50ab8edd1e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088803B2

Reaction notes

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