Hydrochloric Acid → 6-(3,5-dimethylisoxazol-4-yl)-4-((5-fluoropyridin-2-yl)(hydroxy)methyl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1773685Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:26]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=3)[OH:27])[C:10]3[N:14]=[C:13]([O:15]CC)[N:12](C(OC(C)(C)C)=O)[C:11]=3[CH:25]=2)=[C:5]([CH3:35])[O:4][N:3]=1.Cl>C(O)C>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:26]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][N:29]=3)[OH:27])[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:25]=2)=[C:5]([CH3:35])[O:4][N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To tert-butyl 6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-4-((5-fluoropyridin-2-yl)(hydroxy)methyl)-1H-benzo[d]imidazole-1-carboxylate (41.2 mg, 0.09 mmol) in ethanol (5 mL) was added hydrochloric acid (0.66 mL, 2.64 mmol, 4 M in 1,4-dioxane). The mixture was heated to 60° C. for 6 hours and then concentrated in vacuo. Purification by reverse-phase HPLC (25-50% acetonitrile/water with 0.01% trifluoroacetic acid, Gemini C18 5μ) afforded 6-(3,5-dimethylisoxazol-4-yl)-4-((5-fluoropyridin-2-yl)(hydroxy)methyl)-1H-benzo[d]imidazol-2(3H)-one as a white solid.

Workup

concentrationconcentrated in vacuo
customPurification by reverse-phase HPLC (25-50% acetonitrile/water with 0.01% trifluoroacetic acid, Gemini C18 5μ)

Sources & evidence

ORD record: ord-8cd85867cc8d466aa7320c2dea9a9776
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

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