Tetrahydrofuran → HCID 14347365, compound

HRID 2232884Notes

Reaction equation

HRID 2232884 reaction equation
[N+](C1C=CC([O:10][C:11](=O)/[CH:12]=[CH:13]/[CH:14]=[C:15](/[C:22]2[CH:27]=[CH:26][C:25](OC)=[CH:24][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:26]1[CH:27]=[C:22](/[C:15](/[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:14]\[CH:13]=[CH:12]\[C:11]([NH:41][CH2:40][CH2:39][CH2:38][CH2:37][C:33]2[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=2)=[O:10])[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 72927Pyridine, 3-(4-aminobutyl)-HCID 14547249HCID 14547249, compound

Product 1

HCID 14347365HCID 14347365, compound

Procedure

As described in Example 134, (E,E)-5-(4-methoxyphenyl)-5-phenyl-2,4-pentadienoic acid 4-nitrophenyl ester (3.3 g) and 3-pyridinebutanamine (1.24 g) in tetrahydrofuran (20 mL) was stirred for 1 hour at room temperatrure. After the usual work up, the crude amide was purified by HPLC (ethyl acetate) and crystallized from ethyl acetate to furnish 2.7 g of (2E,4Z)-5-(3-methoxyphenyl)-5-phenyl-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide, mp 89°-91° C. A portion was recrystallized from the same solvent to provide the pure amide, mp 90°-92° C. Anal. Calcd for C27H28N2O2 : C, 78.61; H, 6.84; N, 6.79 Found: C, 78.88; H, 6.87; N, 6.66

Workup

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

Sources & evidence

ORD record
ord-d8e8751450f94067ab2c0235a12cbb66
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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