Cyclohexylamine → ethyl (Z)-3-[3'-(3-cyclohexyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylate

HRID 390685Notes

Reaction equation

HRID 390685 reaction equation
[CH2:1]([O:3]/[C:4](=[CH:10]\[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH3:36])[C:24]([O:26]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH:18]=2)=[CH:13][CH:12]=1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].[CH:37]1([NH2:43])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>>[CH:37]1([NH:43][C:24](=[O:26])[N:23]([C:19]2[CH:18]=[C:17]([C:14]3[CH:13]=[CH:12][C:11](/[CH:10]=[C:4](\[O:3][CH2:1][CH3:2])/[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:16][CH:15]=3)[CH:22]=[CH:21][CH:20]=2)[CH3:36])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

3

Reactant 2

HCID 7965CyclohexylamineHCID 86626081ethyl (Z)-2-ethoxy-3-{3'-[methyl(4-nitrophenoxycarbonyl)amino]biphenyl-4-yl}acrylate

Product 1

HCID 86626118ethyl (Z)-3-[3'-(3-cyclohexyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylateYield 51.8%

Procedure

In a manner similar to that of Example 43d, starting with 1.75 g (3 mmol) of ethyl (Z)-2-ethoxy-3-{3′-[methyl(4-nitrophenoxycarbonyl)amino]biphenyl-4-yl}acrylate (prepared according to Example 43c) and 0.42 mL (3.7 mmol) of cyclohexylamine, 0.7 g (50%) of ethyl (Z)-3-[3′-(3-cyclohexyl-1-methylureido)biphenyl-4-yl]-2-ethoxyacrylate is obtained.

Sources & evidence

ORD record
ord-17993720cd4241d08709f1052e2e806d
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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