Tetrahydrofuran → HCID 22155197, compound

HRID 1110547Notes

Reaction equation

HRID 1110547 reaction equation
[N+](C1C=CC(O[C:11](=[O:30])/[CH:12]=[CH:13]/[CH:14]=[C:15](/[C:22]2[CH:27]=[CH:26][CH:25]=[C:24](OC)[CH:23]=2)\[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=CC=1)([O-])=O.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][CH2:38][CH2:39][CH2:40][NH2:41])[CH:32]=1.[O:42]1CCC[CH2:43]1>>[CH3:43][O:42][C:27]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1/[C:15](/[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:14]/[CH:13]=[CH:12]/[C:11]([NH:41][CH2:40][CH2:39][CH2:38][CH2:37][C:33]1[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=1)=[O:30]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 72927Pyridine, 3-(4-aminobutyl)-HCID 14347319HCID 14347319, compound

Product 1

HCID 22155197HCID 22155197, compound

Procedure

As in Example 134, a solution of (2E,4E)-5-(3-methoxyphenyl)-5-phenyl-2,4-pentadienoic acid 4-nitrophenyl ester (2.96 g) and 3-pyridinebutanamine (1.107 g) in tetrahydrofuran (15 mL) was stirred for 1 hour at room temperature. After the usual work up, the crude amide was purified by HPLC (ethyl acetate) and then crystallized from ethyl acetate-hexane to provide 2.5 g of (2E,4E)-5-(methoxyphenyl)-5-phenyl-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide mp 66°-68° C. Anal. Calculated for C28H28N2O2 : C, 78.61; H, 6.84; N. 6.79 Found: C, 78.42; H, 6.88; N, 6.79.

Workup

  1. customAfter the usual work up, the crude amide was purified by HPLC (ethyl acetate)
  2. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9ed0a5b4683b400ca8319e10a4050d16
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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