(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester → (E)-5,5-bis(4-methoxyphenyl)-N-[1-[3-(3-pyridinyl)propyl]-4-(3-pyridinyl)butyl]-2,4-pentadienamide

HRID 2232876Notes

Reaction equation

HRID 2232876 reaction equation
[N+](C1C=CC([O:10][C:11](=O)/[CH:12]=[CH:13]/[CH:14]=[C:15]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=CC=1)([O-])=O.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH2:40][CH2:41][CH:42]([NH2:52])[CH2:43][CH2:44][CH2:45][C:46]2[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=2)[CH:34]=1>O1CCCC1>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:14]/[CH:13]=[CH:12]/[C:11]([NH:52][CH:42]([CH2:41][CH2:40][CH2:39][C:35]2[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=2)[CH2:43][CH2:44][CH2:45][C:46]2[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=2)=[O:10])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 14347315(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl esterHCID 14994128alpha-[3-(3-Pyridinyl)propyl]-3-pyridinebutanamine

Product 1

HCID 14994131(E)-5,5-bis(4-methoxyphenyl)-N-[1-[3-(3-pyridinyl)propyl]-4-(3-pyridinyl)butyl]-2,4-pentadienamideYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As before in Example 134, a solution of (E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (1.94 g) and alpha-[3-(3-pyridinyl)propyl]-3-pyridinebutanamine (1.21 g) in tetrahydrofuran (25 mL) was stirred for 20 hours at 50° C. and then was worked up in the normal manner. The crude was purified by HPLC (ethyl acetate-triethylamine; 19:1) and was then lyophilized from benzene to give 1.95 g of (E)-5,5-bis-(4-methoxyphenyl)-N-[1-[3-(3-pyridinyl)propyl]-4-(3-pyridinyl)-butyl]-2,4-pentadienamide as a glass.

Workup

  1. customThe crude was purified by HPLC (ethyl acetate-triethylamine; 19:1)

Sources & evidence

ORD record
ord-951fbce7f44f46ff90a8aa83803b7c72
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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