Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1) → HCID 58986339, compound

HRID 420813Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([C:19]([NH:21][NH2:22])=[O:20])=[C:9]1[CH:23]([CH3:25])[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:27](=N)(OCC)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CCO>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([C:19]2[O:20][C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:22][N:21]=2)=[C:9]1[CH:23]([CH3:25])[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-benzyl-2-isopropyl-5-methoxy-1H-indole-3-carbohydrazide (Compound 35, 25 mg, 0.074 mmol) in EtOH (2.0 ml) was added ethyl benzimidate hydrochloride (Fluka, 21 mg, 0.11 mmol). The mixture was stirred at 80° C. for 4 h and was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with 0-30% EtOAc-hexanes to yield 2-(1-benzyl-2-isopropyl-5-methoxy-1H-indol-3-yl)-5-phenyl-1,3,4-oxadiazole (Compound 36) as a white solid.

Workup

concentrationwas concentrated in vacuo
customThe residue was purified by flash chromatography on silica gel eluting with 0-30% EtOAc-hexanes

Sources & evidence

ORD record: ord-c5c217d05f704a728dc0590b85acc8fc
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097644B2

Reaction notes

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