Dimethylamine → [5-(4-Iodophenyl)-[1,3,4]oxadiazol-2-ylmethyl]-dimethylamine

HRID 31407

Reaction equation

Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)=[N:6][N:7]=1.[I-].[K+].[CH3:17][NH:18][CH3:19]>O1CCCC1>[I:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[O:4][C:3]([CH2:2][N:18]([CH3:19])[CH3:17])=[N:7][N:6]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 20 °C

Procedure

2-Chloromethyl-5-(4-iodophenyl)-[1,3,4]oxadiazole (Intermediate 7) (48 mg, 0.15 mmol) and potassium iodide (25 mg, 0.15 mmol) were dissolved in 2M dimethylamine in tetrahydrofuran (2 ml) and stirred for 18 hours at 20° C. The reaction was evaporated to dryness in vacuo and the product was purified on a 10 g silica SPE cartridge (stepped solvent gradient 80:20 ethyl acetate:cyclohexane, 100% ethyl acetate, 95:5 ethyl acetate:methanol).

Workup

customThe reaction was evaporated to dryness in vacuo
customthe product was purified on a 10 g silica SPE cartridge (stepped solvent gradient 80:20 ethyl acetate:cyclohexane, 100% ethyl acetate, 95:5 ethyl acetate:methanol)

Sources & evidence

ORD record: ord-c2559fa983e245c3a7bffa15abcab064
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425555B2

Linked notes

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