N,2-dimethoxy-N-methyl-2-(4-morpholinophenyl)acetamide → 2,6-Dimethoxy-4-(5-(2-methoxy-2-(4-morpholinophenyl)acetyl)furan-2-yl)phenyl benzoate

HRID 56540Notes

Reaction equation

HRID 56540 reaction equation
[C:1]([O:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)=[CH:12][C:11]=1[O:23][CH3:24])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CON(C)[C:28](=[O:44])[CH:29]([O:42][CH3:43])[C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1>>[C:1]([O:9][C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([C:18]2[O:19][C:20]([C:28](=[O:44])[CH:29]([O:42][CH3:43])[C:30]3[CH:31]=[CH:32][C:33]([N:36]4[CH2:37][CH2:38][O:39][CH2:40][CH2:41]4)=[CH:34][CH:35]=3)=[CH:21][CH:22]=2)=[CH:12][C:11]=1[O:23][CH3:24])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 58431993N,2-dimethoxy-N-methyl-2-(4-morpholinophenyl)acetamideHCID 584319964-(Furan-2-yl)-2,6-dimethoxyphenyl benzoate

Product 1

HCID 584321602,6-Dimethoxy-4-(5-(2-methoxy-2-(4-morpholinophenyl)acetyl)furan-2-yl)phenyl benzoateYield 50%

Conditions

Temperature
0 °C

Procedure

4-(Furan-2-yl)-2,6-dimethoxyphenyl benzoate was reacted with N,2-dimethoxy-N-methyl-2-(4-morpholinophenyl)acetamide according to the procedure described for the synthesis of Example 12 except that the reaction was warmed to only 0° C. Purification by chromatography (EtOAc-hexanes) provided 2,6-dimethoxy-4-(5-(2-methoxy-2-(4-morpholinophenyl)acetyl)furan-2-yl)phenyl benzoate as a yellow solid (0.257 g, 50% yield). MS: m/z 558.2 [M+H]+.

Workup

  1. customdescribed for the synthesis of Example 12 except that the reaction
  2. customPurification by chromatography (EtOAc-hexanes)

Sources & evidence

ORD record
ord-13cf5c8728c74cb08f54c85edd9ee93c
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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