N,2-dimethoxy-N-methyl-2-(4-morpholinophenyl)acetamide → 1-(5-(4-Ethoxy-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(4-morpholinophenyl)ethanone

HRID 512648Notes

Reaction equation

HRID 512648 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[CH:6][C:5]=1[O:17][CH3:18])[CH3:2].CON(C)[C:22](=[O:38])[CH:23]([O:36][CH3:37])[C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1>>[CH2:1]([O:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C:12]2[O:13][C:14]([C:22](=[O:38])[CH:23]([O:36][CH3:37])[C:24]3[CH:25]=[CH:26][C:27]([N:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)=[CH:28][CH:29]=3)=[CH:15][CH:16]=2)=[CH:6][C:5]=1[O:17][CH3:18])[CH3:2]

Participants

3

Reactant 2

HCID 58431993N,2-dimethoxy-N-methyl-2-(4-morpholinophenyl)acetamideHCID 584320402-(4-Ethoxy-3,5-dimethoxyphenyl)furan

Product 1

HCID 584320891-(5-(4-Ethoxy-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(4-morpholinophenyl)ethanoneYield 58%

Procedure

2-(4-Ethoxy-3,5-dimethoxyphenyl)furan was coupled with N,2-dimethoxy-N-methyl-2-(4-morpholinophenyl)acetamide according to the procedure for the synthesis of Example 12. Purification by chromatography (EtOAc-hexanes) gave 1-(5-(4-ethoxy-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(4-morpholinophenyl)ethanone as a yellow foam (0.263 g, 58% yield). MS: m/z 482.2 [M+H]+.

Workup

  1. customPurification by chromatography (EtOAc-hexanes)

Sources & evidence

ORD record
ord-5dbf0fa519e74d9a84e6fd9ee9264621
Source dataset
uspto-grants-2015_08
Patent number
US09102643B2

Reaction notes

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