Ethyl Acetate → 5-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74187

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([CH:16]=1)[NH2:15].[CH:24](OCC)(OCC)OCC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:24]=[N:15][C:14]=2[CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (0.20 g, 0.646 mmol), triethyl orthoformate (5 mL) was added a catalytic amount of p-toluenesulfonic acid monohydrate, and this was heated to 100° C. for 1.5 hours. The reaction mixture was cooled, ethyl acetate and water added, and this was extracted. This was washed with water, dried over magnesium sulfate, and after concentration the precipitated crystals were filtered off. These were washed with a hexane/ethyl acetate mixture solution, and dried to yield the title compound (65 mg, 31.5% yield) as light reddish-brown crystals.

Workup

temperatureThe reaction mixture was cooled
extractionthis was extracted
washThis was washed with water
dry with materialdried over magnesium sulfate
concentrationafter concentration the precipitated crystals
filtrationwere filtered off
washThese were washed with a hexane/ethyl acetate mixture solution
customdried

Sources & evidence

ORD record: ord-7fb7c65b3cb14bfebba4c88cb89f09ce
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829035B2

Linked notes

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