Diisopropylethylamine → N-(3,3-dimethylbutyl)-2-[2-(2,2-dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]-N-ethylacetamide

HRID 2103771Notes

Reaction equation

[C:1]([C:5]1[O:6][C:7](=[O:20])[CH:8]=[C:9]2[C:13]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:12]=3[O:11][C:10]=12)([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:22]([NH:24][CH2:25][CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:23].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:28][C:27]([CH3:30])([CH3:29])[CH2:26][CH2:25][N:24]([CH2:22][CH3:23])[C:7](=[O:20])[CH2:8][C:9]1[C:13]2[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:12]=2[O:11][C:10]=1[C:5](=[O:6])[C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 45 °C

Procedure

To a mixture containing 21.8 mg 1-tert-butyl-6-methoxy-3H-pyrano[3,4-b][1]benzofuran-3-one from the Step B above and 21.6 mg N-Ethyl-3,3-dimethylbutan-1-amine hydrochloride from the Step A above in 0.75 mL DMF was 26 μL DIEA. The mixture was heated in 45° C. oil bath over night. It was purified directly on RP-HPLC using 65˜85% MeCN gradient. The fractions containing pure product were pooled and lyophilized to give the title compound. LC-MS: 4.38 min. (m/Z=318.2, 402.3, 424.3). Alternative preparation of N-(3,3-dimethylbutyl)-2-[2-(2,2-dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]-N-ethylacetamide

Workup

customIt was purified directly on RP-HPLC using 65˜85% MeCN gradient
additionThe fractions containing pure product

Sources & evidence

ORD record: ord-4d3c0996dc494393b03e7262f068ea72
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576122B2

Reaction notes

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