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

HRID 1110549
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HRID 1110549 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-220143f3437d4f3a8bb1677f7f5a7e15
출처 데이터셋
uspto-grants-1990_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04975438

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