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Pyridine, 3-(4-aminobutyl)- → (Z)-5,5-bis(3-methoxyphenyl)-N-[4-(3-pyridinyl)-butyl]-2,4-pentadienamide

HRID 1110549
ノート
印刷プレビュー

反応式

HRID 1110549 の反応式
[N+](C1C=CC([O:10][C:11](=O)/[CH:12]=[CH:13]\[CH:14]=[C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[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:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH2:40][CH2:41][CH2:42][NH2:43])[CH:34]=1.[N+](C1C=C(C(C2C=CC=C([N+]([O-])=O)C=2)=C/C=C/C(NCCCCC2C=NC=CC=2)=O)C=CC=1)([O-])=O>O1CCCC1>[CH3:23][O:22][C:18]1[CH:17]=[C:16]([C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)=[CH:14]/[CH:13]=[CH:12]\[C:11]([NH:43][CH2:42][CH2:41][CH2:40][CH2:39][C:35]2[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=2)=[O:10])[CH:21]=[CH:20][CH:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 72927Pyridine, 3-(4-aminobutyl)-HCID 14347313(Z)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl esterHCID 14347344(E)-5,5-bis(3-nitrophenyl)-N-[4-(3-pyridinyl)butyl)-2,4-pentadienamide

生成物 1

HCID 14347335(Z)-5,5-bis(3-methoxyphenyl)-N-[4-(3-pyridinyl)-butyl]-2,4-pentadienamide収率 39%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

As in Example 134, a solution of (Z)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (1.2 g) and 3-pyridinebutanamine (0.42 g) in tetrahydrofuran (7 mL) was stirred at room temperature for 1 hour. The crude amide that had been isolated in the usual way, was contaminated with a minor amount of the (E)-isomer. The mixture was separated by HPLC (ethyl acetate) and the desired product was crystallized from ether (2x) to yield 0.48 g of (Z)-5,5-bis(3-methoxyphenyl)- N-[4-(3-pyridinyl)-butyl]-2,4-pentadienamide mp 69°-73° C. Anal. Calculated for C28H30N2O3 : C, 75.99; H, 6.83; N, 6.33 Found: C, 75.79; H, 6.70; N, 6.39.

後処理

  1. customThe crude amide that had been isolated in the usual way
  2. customThe mixture was separated by HPLC (ethyl acetate)
  3. customthe desired product was crystallized from ether (2x)

出典と根拠

ORDレコード
ord-220143f3437d4f3a8bb1677f7f5a7e15
出典データセット
uspto-grants-1990_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04975438

反応ノート

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