Methylamine → 3-(3-iodo-1-tosyl-1H-indol-5-yl)-N-methyl-1,2,4-oxadiazol-5-amine

HRID 634282Notes

Reaction equation

[CH3:1][NH2:2].[I:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]3[N:17]=[C:16](C(Cl)(Cl)Cl)[O:15][N:14]=3)[CH:11]=2)[N:6]([S:22]([C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:5]=1>O>[I:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]3[N:17]=[C:16]([NH:2][CH3:1])[O:15][N:14]=3)[CH:11]=2)[N:6]([S:22]([C:25]2[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=2)(=[O:23])=[O:24])[CH:5]=1

Participants

Conditions

Temperature: 90 °C

Procedure

N-Methylamine (1M in THF) (5 mL) was added to a sealed tube equipped with magnetic stir bar followed by the addition of 3-(3-iodo-1-tosyl-1H-indol-5-yl)-5-(trichloromethyl)-1,2,4-oxadiazole (250 mg, 0.43 mmol). The tube was sealed and heated at 90° C. in oil bath for 12 h. After completion of the reaction, it was cooled to RT. The mixture was treated with water and extracted with EtOAc (2×20 mL). The organic layer was dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified with basic alumina column chromatography (eluent: 40% EtOAc in petroleum ether) to give 3-(3-iodo-1-tosyl-1H-indol-5-yl)-N-methyl-1,2,4-oxadiazol-5-amine (200 mg, 94.3%) as an off white solid. MS (ESI, pos. ion) m/z: 495.0 (M+1).

Workup

customequipped with magnetic stir bar
customThe tube was sealed
customAfter completion of the reaction, it
temperaturewas cooled to RT
extractionextracted with EtOAc (2×20 mL)
dry with materialThe organic layer was dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified with basic alumina column chromatography (eluent: 40% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-2f1ed0729cbf45be8e002f44ec0ad615
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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