(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester → (E)-N-[3-(8-isoquinolinyl) propyl]-5,5-bis(4-methoxyphenyl)-2,4-pentadienamide

HRID 1110626Notes

Reaction equation

HRID 1110626 reaction equation
[N+](C1C=CC(O[C:11](=[O:32])/[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][C:41]=2[CH2:43][CH2:44][CH2:45][NH2:46])[CH:36]=[CH:35][N:34]=1>O1CCCC1>[CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][C:41]=2[CH2:43][CH2:44][CH2:45][NH:46][C:11](=[O:32])/[CH:12]=[CH:13]/[CH:14]=[C:15]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[CH:36]=[CH:35][N:34]=1

Participants

4

Reactant 2

HCID 14347315(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl esterHCID 149941278-Isoquinolinepropanamine

Product 1

HCID 14347375(E)-N-[3-(8-isoquinolinyl) propyl]-5,5-bis(4-methoxyphenyl)-2,4-pentadienamideYield 68.4%

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 (0.24 g) and 8-isoquinolinepropanamine (0.103 g) in tetrahydrofuran (5 mL) was stirred for 17 hours at room temperature and was worked up in the usual manner. The crude amide was purified by HPLC (ethyl acetate) and then was crystallized from ethyl acetatehexane to afford 0.181 g of (E)-N-[3-(8-isoquinolinyl) propyl]-5.5-bis(4-methoxyphenyl)-2,4-pentadienamide, mp 115°-118° C.

Workup

  1. customThe crude amide was purified by HPLC (ethyl acetate)
  2. customwas crystallized from ethyl acetatehexane

Sources & evidence

ORD record
ord-6d036a7fb2924bf088b990752b35dafa
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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