Tetrahydrofuran → HCID 10224553, compound

HRID 1393539Notes

Reaction equation

[C:1]1([N:7]2[C:11]3[CH:12]=[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=O)[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)([N:33]1C=CN=C1)=O.[O:43]1[CH2:47]CCC1>C(OCC)(=O)C>[CH3:47][O:43][NH:33][C:22](=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]2[N:9]=[C:8]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:11]=2[CH:12]=1

Participants

Conditions

Temperature: 20 °C

Procedure

100 mg of 6-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]hexanoic acid was dissolved in 2 ml of tetrahydrofuran, mixed with 39 mg of carbonyldiimidazole, stirred for 30 minutes at 20° C. and then refluxed for 30 minutes. At 20° C., 21 mg of O-methylhydroxyaminohydrochloride was then added, and it was allowed to stir for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with 2N aqueous hydrochloric acid and saturated potassium bicarbonate solution. After drying on sodium sulfate, it was concentrated by evaporation in a vacuum, and the residue was chromatographed on silica gel.

Workup

temperaturerefluxed for 30 minutes
additionAt 20° C., 21 mg of O-methylhydroxyaminohydrochloride was then added
stirringto stir for 18 hours
washwashed with 2N aqueous hydrochloric acid and saturated potassium bicarbonate solution
customAfter drying on sodium sulfate, it
concentrationwas concentrated by evaporation in a vacuum
customthe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-bcad3a2f8007493c89a9c4b34c053171
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345075B2

Reaction notes

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