2-(3,4,5-Trimethoxyphenyl)furan → 2-(4-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxy-1-(5-(3,4,5-trimethoxyphenyl)furan-2-yl)ethanone

HRID 56595Notes

Reaction equation

HRID 56595 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH:18]1([C:21]2[O:25][C:24]([C:26]3[CH:31]=[CH:30][C:29]([CH:32]([O:39][CH3:40])[C:33](N(OC)C)=[O:34])=[CH:28][CH:27]=3)=[N:23][N:22]=2)[CH2:20][CH2:19]1>>[CH:18]1([C:21]2[O:25][C:24]([C:26]3[CH:31]=[CH:30][C:29]([CH:32]([O:39][CH3:40])[C:33]([C:15]4[O:14][C:13]([C:5]5[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=5)=[CH:17][CH:16]=4)=[O:34])=[CH:28][CH:27]=3)=[N:23][N:22]=2)[CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 508768262-(3,4,5-Trimethoxyphenyl)furanHCID 584320202-(4-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)phenyl)-N,2-dimethoxy-N-methylacetamide

Product 1

HCID 584321292-(4-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxy-1-(5-(3,4,5-trimethoxyphenyl)furan-2-yl)ethanone

Procedure

2-(4-(5-Cyclopropyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxy-1-(5-(3,4,5-trimethoxyphenyl)furan-2-yl)ethanone was prepared from 2-(3,4,5-trimethoxyphenyl)furan and 2-(4-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)phenyl)-N,2-dimethoxy-N-methylacetamide according to the procedure used in Example 30. Purification by chromatography (60% EtOAc-hexanes) gave the product as a pale yellow solid (0.129 g, 42% yield). MS: m/z 491.1 [M+H]+.

Workup

  1. customPurification by chromatography (60% EtOAc-hexanes)

Sources & evidence

ORD record
ord-805c38925bfe49e790f1adb882a7d7b8
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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