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

HRID 1110625Notes

Reaction equation

HRID 1110625 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.[CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]([CH2:43][CH2:44][CH2:45][CH2:46][NH2:47])=[CH:35][N:34]=1>O1CCCC1>[CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]([CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:11](=[O:10])/[CH:12]=[CH:13]/[CH:14]=[C:15]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:35][N:34]=1

Participants

4

Reactant 2

HCID 14347315(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl esterHCID 149941264-Isoquinolinebutanamine

Product 1

HCID 14347374(E)-N-[4-(4-isoquinolinyl)butyl]-5,5-bis(4-methoxyphenyl)-2,4-pentadienamideYield 29.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 134, a solution of (E)-5,5-bis-(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (0.841 g) and 4-isoquinolinebutanamine (0.39 g) in tetrahydrofuran (8 mL) was stirred for 17 hours at room temperature and was worked up in the usual manner. The crude product was purified by HPLC (ethyl acetate-hexane; 3:1) and then was crystallized from ethyl acetate-ether to provide 0.284 g of (E)-N-[4-(4-isoquinolinyl)butyl]-5.5-bis(4-methoxyphenyl)-2,4-pentadienamide, mp 91°-93° C.

Workup

  1. customThe crude product was purified by HPLC (ethyl acetate-hexane; 3:1)
  2. customwas crystallized from ethyl acetate-ether

Sources & evidence

ORD record
ord-de0c32790eee438f9da99ceaedb5e64b
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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