Boron trifluoride etherate → [1-(3-[1,2,4]oxadiazol-3-yl-propyl)-1H-benzoimidazol-2-yl]-methanol

HRID 1835838Notes

Reaction equation

[OH:1][NH:2][C:3](=[NH:18])[CH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][OH:17].B(F)(F)F.[CH3:23]COCC>C(OC)(OC)OC>[O:1]1[CH:23]=[N:18][C:3]([CH2:4][CH2:5][CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:16][OH:17])=[N:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of N-hydroxy-4-(2-hydroxymethyl-benzoimidazol-1-yl)-butyramidine, 203, (500 mg, 2.01 mmol) in trimethyl orthoformate (5 mL) in the presence of BF3.OEt2 (50 μL) in a sealed tube was placed in a microwave oven (Smith Creator, Personal Chemistry) and heated at 100° C. for 15 min while stirring, resulting in the dissolution of all the material. The reaction was repeated 5 times. The 6 batches were combined and concentrated in vacuo. The residue was treated with 1M HCl (15 mL) and THF (15 mL) and left overnight. Concentration followed by trituration from dichloromethane and recrystallization from isopropyl alcohol and methanol afforded [1-(3-[1,2,4]oxadiazol-3-yl-propyl)-1H-benzoimidazol-2-yl]-methanol (2.28 g, 73%) as a white solid:

Workup

customwas placed in a microwave oven
customresulting in the dissolution of all the material
concentrationconcentrated in vacuo
additionThe residue was treated with 1M HCl (15 mL) and THF (15 mL)
concentrationConcentration
customfollowed by trituration from dichloromethane and recrystallization from isopropyl alcohol and methanol

Sources & evidence

ORD record: ord-97fb9c1b36aa453485dd1ac4b8d82009
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06774134B2

Reaction notes

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