Boron trifluoride etherate → 1-isopropyl-3-[1-(3-methyl-butyl)-5-[1,2,4]oxadiazol-3-yl-1H-benzoimidazol-2-ylmethyl]-1,3-dihydro-benzoimidazol-2-one

HRID 896376Notes

Reaction equation

[OH:1][NH:2][C:3]([C:5]1[CH:32]=[CH:31][C:8]2[N:9]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:10]([CH2:12][N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[N:15]([CH:22]([CH3:24])[CH3:23])[C:14]3=[O:25])=[N:11][C:7]=2[CH:6]=1)=[NH:4].B(F)(F)F.[CH3:37]COCC>C(OC)(OC)OC>[CH:22]([N:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:13]([CH2:12][C:10]2[N:9]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:8]3[CH:31]=[CH:32][C:5]([C:3]4[N:4]=[CH:37][O:1][N:2]=4)=[CH:6][C:7]=3[N:11]=2)[C:14]1=[O:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of N-hydroxy-2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxamidine (65 mg, 0.15 mmol) in trimethyl orthoformate (4 mL) in the presence of BF3.OEt2 (5 μL) in a sealed tube was placed in a microwave oven (Smith Creator, Personal Chemistry) and heated at 80° C. for 5 min while stirring. The solvent was removed in vacuo and purified by flash chromatography (eluent hexane-acetone 3:1) to give 1-isopropyl-3-[1-(3-methyl-butyl)-5-[1,2,4]oxadiazol-3-yl-1H-benzoimidazol-2-ylmethyl]-1,3-dihydro-benzoimidazol-2-one (35 mg, 53%) as a white solid:

Workup

customThe solvent was removed in vacuo
custompurified by flash chromatography (eluent hexane-acetone 3:1)

Sources & evidence

ORD record: ord-078b7eb63a234f398968f1e21687e012
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919331B2

Reaction notes

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