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

HRID 1110536Notes

Reaction equation

HRID 1110536 reaction equation
[N+](C1C=CC(O[C:11](=[O:30])/[CH:12]=[CH:13]/[CH:14]=[C:15]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=CC=1)([O-])=O.[CH3:31][C:32]([CH3:43])([NH2:42])[CH2:33][CH2:34][CH2:35][C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1>O1CCCC1>[F:29][C:26]1[CH:25]=[CH:24][C:23]([C:15]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:14]/[CH:13]=[CH:12]/[C:11]([NH:42][C:32]([CH3:43])([CH3:31])[CH2:33][CH2:34][CH2:35][C:36]2[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=2)=[O:30])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 14347312(E)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acid 4-nitrophenyl esterHCID 14547286alpha,alpha-Dimethyl-3-pyridinebutanamine

Product 1

HCID 14347333(E)-5,5-bis(4-fluorophenyl)-N-[1,1-dimethyl-4-(3-pyridinyl)butyl]-2,4-pentadienamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 134, a solution of (E)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (1.63 g) and alpha,alpha-dimethyl-3-pyridinebutanamine (0.9 mL) in tetrahydrofuran (20 mL) was stirred at reflux for 24 hours. The crude product, isolated in the usual manner, was crystallized from ethyl acetate to yield 1.6 g of (E)-5,5-bis(4-fluorophenyl)-N-[1,1-dimethyl-4-(3-pyridinyl)butyl]-2,4-pentadienamide, mp 163.5°-164.5° C. Anal. Calculated for C28H28F2N2O: C, 75.32; H, 6.32; F, 8.51; N, 6.27 Found: C, 75.23; H, 6.48; F, 8.39; N, 6.22.

Workup

  1. temperatureat reflux for 24 hours
  2. customThe crude product, isolated in the usual manner
  3. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-a8c26fb0df424a6997a48d6f7af3c1d9
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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