Methanol → 2-(4-Cyclopropylpiperazin-1-yl)benzooxazole-5-carboxaldehyde

HRID 1944702Notes

Reaction equation

[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][C:16]([C:19]#N)=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C.C[OH:31].O>C1COCC1.C1(C)C=CC=CC=1>[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][C:16]([CH:19]=[O:31])=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 2-(4-cyclopropylpiperazin-1-yl)benzooxazole-5-carbonitrile (1.5 g, 5.6 mmol) in THF-toluene (50 mL, 2:1) was added DIBAL (16.8 mL, 16.8 mmol) dropwise at −78° C. under a nitrogen atmosphere. Then the mixture was allowed to warm to 20° C. and then stirred for 1 h. Methanol (5 mL) was added dropwise, followed by water (20 mL). The mixture was extracted with ethyl acetate (3×20 mL) and the combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by column chromatography on silica gel (elute: 2% dichloromethane in methanol) to give 1.1 g (72%) of 2-(4-cyclopropylpiperazin-1-yl)benzooxazole-5-carboxaldehyde.

Workup

extractionThe mixture was extracted with ethyl acetate (3×20 mL)
dry with materialthe combined organic extracts were dried (Na2SO4)
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (elute: 2% dichloromethane in methanol)

Sources & evidence

ORD record: ord-3d14c7ea5a20432a97b06f703e54dccc
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394842B2

Reaction notes

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