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

HRID 1760555Notes

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

1H NMR (DMSO) δ 1.97-2.06 (m, 4H), 4.27 (t, 2H, J=7.4 Hz), 4.72 (s, 2H), 5.44 (br s, 2H), 5.64 (br s, 1H), 7.18 (t, 1H, J=7.5 Hz), 7.23 (t, 1H, J=7.5 Hz), 7.57 (d, 1H, J=7.5 Hz), 7.59 (d, 1H, J=7.5 Hz), 8.83 (s, 1H); MS m/e 249 (MH+); [1-(3-[1,2,4]Oxadiazol-3-yl-propyl)-1H-benzoiidazol-2-yl]-methanol 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 treted 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
concentrationConcentration
customfollowed by trituration from dichloromethane and recrystallization from isopropyl alcohol and methanol

Sources & evidence

ORD record: ord-14e94cd84e3b401c8d2331664db79096
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06844342B2

Reaction notes

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