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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-(9-Amino-6-chloro-1,2,3,4-tetrahydro-acridin-3-yl-methyl)-2-[1,2]dithiolan-3-yl-acetamide

HRID 969289
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 969289
[NH2:1][CH2:2][CH:3]1[CH2:16][C:15]2[C:6](=[C:7]([NH2:18])[C:8]3[C:13]([N:14]=2)=[CH:12][C:11]([Cl:17])=[CH:10][CH:9]=3)[CH2:5][CH2:4]1.[S:19]1[CH2:23][CH2:22][CH:21]([CH2:24][C:25](O)=[O:26])[S:20]1.C1[C@@H](CC(O)=O)SSC1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[NH2:18][C:7]1[C:8]2[C:13]([N:14]=[C:15]3[C:6]=1[CH2:5][CH2:4][CH:3]([CH2:2][NH:1][C:25](=[O:26])[CH2:24][CH:21]1[CH2:22][CH2:23][S:19][S:20]1)[CH2:16]3)=[CH:12][C:11]([Cl:17])=[CH:10][CH:9]=2
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Komponenten

6

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 108666812-(1,2-Dithiolan-3-YL)acetic acid2×HCID 29923430Trisnorlipoic acidHCID 590174273-Aminomethyl-6-chloro-1,2,3,4-tetrahydroacridin-9-ylamine

Produkt 1

HCID 86615208N-(9-Amino-6-chloro-1,2,3,4-tetrahydro-acridin-3-yl-methyl)-2-[1,2]dithiolan-3-yl-acetamide
Ausbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 16 (140 mg, 0.53 mmol) and [1,2]dithiolan-3-yl-acetic acid (Chen, Yaun-Shek and Lawton, Richard G. An efficient synthetic route to 2-(1,2-dithiolan-3-yl)acetic acid. Trisnorlipoic acid and amide derivatives. Tetrahedron Letters 1997, 38, 5785-5788) (90 mg, 0.55 mmol) in anhydrous DMF (5 mL), under N2, was cooled to 0° C. and then additioned with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (113 mg, 0.59 mmol); the reaction mixture was stirred at 0° C. for 15 min and then at room temperature for 2 h in the dark. Solvent was then evaporated, accurately avoiding heating up the mixture. An oily residue was obtained which was purified by gravity column. Elution with petroleum ether/CH2Cl2/MeOH/aqueous 30% ammonia solution (5:4:1:0.1) afforded 17 as a waxy solid: 40% yield; 1H NMR (200 MHz, CD3OD) δ 8.03 (d, J=9.2 Hz, 1H), 7.67 (d, J=2.2 Hz, 1H), 7.30 (dd, J=8.8, 2.2 Hz, 1H), 4.05 (m, 1H), 2.95-3.34 (m, 5H), 2.46-2.59 (m, 6H), 1.99-2.20 (m, 3H), 1.48-1.52 (m, 1H). Anal. Calculated for C19H22ClN3OS2: C, 55.93; H, 5.44; N, 10.30. Found: C, 56.01; H, 5.45; N, 10.11.

Aufarbeitung

  1. waitat room temperature for 2 h in the dark
  2. customSolvent was then evaporated
  3. temperatureaccurately avoiding heating up the mixture
  4. customAn oily residue was obtained which
  5. customwas purified by gravity column
  6. washElution with petroleum ether/CH2Cl2/MeOH/aqueous 30% ammonia solution (5:4:1:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-ecf278f2286e48e7a92d6179ab543fd3
Quelldatensatz
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07307083B2

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