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

HRID 56547Notes

Reaction equation

HRID 56547 reaction equation
[F:1][CH:2]([F:19])[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].CON(C)[C:23](=[O:39])[CH:24]([O:37][CH3:38])[C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1>>[F:19][CH:2]([F:1])[O:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([C:12]2[O:13][C:14]([C:23](=[O:39])[CH:24]([O:37][CH3:38])[C:25]3[CH:26]=[CH:27][C:28]([N:31]4[CH2:32][CH2:33][O:34][CH2:35][CH2:36]4)=[CH:29][CH:30]=3)=[CH:15][CH:16]=2)=[CH:6][C:5]=1[O:17][CH3:18]

Participants

3

Reactant 2

HCID 58431993N,2-dimethoxy-N-methyl-2-(4-morpholinophenyl)acetamideHCID 584320532-(4-(Difluoromethoxy)-3,5-dimethoxyphenyl)furan

Product 1

HCID 584320001-(5-(4-(Difluoromethoxy)-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(4-morpholinophenyl)-ethanoneYield 6%

Procedure

2-(4-(Difluoromethoxy)-3,5-dimethoxyphenyl)furan was coupled with N,2-dimethoxy-N-methyl-2-(4-morpholinophenyl)acetamide following the procedure used for the synthesis of Example 12. Purification by chromatography (EtOAc-hexanes) provided 1-(5-(4-(difluoromethoxy)-3,5-dimethoxyphenyl)furan-2-yl)-2-methoxy-2-(4-morpholinophenyl)-ethanone as a brown oil (0.021 g, 6% yield). MS: m/z 504.2 [M+H]+.

Workup

  1. customused for the synthesis of Example 12
  2. customPurification by chromatography (EtOAc-hexanes)

Sources & evidence

ORD record
ord-c73627c4b4ad447e950c84396429b740
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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