5-(Furan-2-yl)-2,3-dimethoxybenzonitrile → 2,3-Dimethoxy-5-(5-(2-methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetyl)furan-2-yl)benzonitrile

HRID 1798584Notes

Reaction equation

HRID 1798584 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([O:16][CH3:17])[C:9]([O:14][CH3:15])=[C:10]([CH:13]=1)[C:11]#[N:12].CON(C)[C:21](=[O:37])[CH:22]([O:35][CH3:36])[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:30][C:31]([CH3:34])=[N:32][N:33]=2)=[CH:25][CH:24]=1>>[CH3:15][O:14][C:9]1[C:8]([O:16][CH3:17])=[CH:7][C:6]([C:2]2[O:1][C:5]([C:21](=[O:37])[CH:22]([O:35][CH3:36])[C:23]3[CH:24]=[CH:25][C:26]([C:29]4[O:30][C:31]([CH3:34])=[N:32][N:33]=4)=[CH:27][CH:28]=3)=[CH:4][CH:3]=2)=[CH:13][C:10]=1[C:11]#[N:12]

Participants

3

Reactant 2

HCID 584320135-(Furan-2-yl)-2,3-dimethoxybenzonitrileHCID 58432086N,2-dimethoxy-N-methyl-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetamide

Product 1

HCID 584319902,3-Dimethoxy-5-(5-(2-methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetyl)furan-2-yl)benzonitrileYield 13%

Procedure

The method used for the final coupling step of Example 12 was followed for the reaction of 5-(furan-2-yl)-2,3-dimethoxybenzonitrile and N,2-dimethoxy-N-methyl-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetamide except that the reaction was performed at −40 to −25° C. then warmed to room temperature. Purification by chromatography (20-100% EtOAc-hexanes) provided 2,3-dimethoxy-5-(5-(2-methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetyl)furan-2-yl)benzonitrile (0.040 g, 13% yield). MS: m/z 460.2 [M+H]+.

Workup

  1. customwas performed at −40 to −25° C.
  2. customPurification by chromatography (20-100% EtOAc-hexanes)

Sources & evidence

ORD record
ord-4a9c8ac3c4614fa7b5a237cfc739c776
Source dataset
uspto-grants-2013_01
Patent number
US08343970B2

Reaction notes

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