Pyridine, 3-(4-aminobutyl)- → HCID 14347367, compound

HRID 1110548Notes

Reaction equation

HRID 1110548 reaction equation
[N+](C1C=CC(O[C:11](=[O:31])/[CH:12]=[CH:13]/[CH:14]=[C:15](/[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)\[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=CC=1)([O-])=O.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][CH2:39][CH2:40][CH2:41][NH2:42])[CH:33]=1>O1CCCC1>[F:30][C:26]1[CH:25]=[C:24](/[C:15](/[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[CH:14]/[CH:13]=[CH:12]/[C:11]([NH:42][CH2:41][CH2:40][CH2:39][CH2:38][C:34]2[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 72927Pyridine, 3-(4-aminobutyl)-HCID 14347321HCID 14347321, compound

Product 1

HCID 14347367HCID 14347367, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 134, a solution of (2E,4E)-5-(3-fluorophenyl)-5-(3-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (1.8 g) and 3-pyridinebutanamine (0.650 g) in tetrahydrofuran (20 mL) was stirred for 17 hours at room temperature. The crude amide, isolated in the usual fashion, was purified by HPLC (ethyl acetate) and then crystallized from ether-hexane to furnish 1.6 g of (2E,4E)-5-(3-fluorophenyl)-5-(3-methoxyphenyl)-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide mp 55°-60° C. A sample was recrystallized from ethyl acetate-hexane to yield the analytical specimen, mp 58°-60° C. Anal. Calculated for C27H27FN2O2 : C, 75.33; H, 6.32; F, 4.41; N, 6.51 Found: C, 75.31; H, 6.34; F, 4.38; N, 6.47.

Workup

  1. customThe crude amide, isolated in the usual fashion
  2. customwas purified by HPLC (ethyl acetate)
  3. customcrystallized from ether-hexane

Sources & evidence

ORD record
ord-d0cdab88fdf64fd489680f7d6b530565
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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