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 969289Notes

Reaction equation

HRID 969289 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-ecf278f2286e48e7a92d6179ab543fd3
Source dataset
uspto-grants-2007_12
Patent number
US07307083B2

Reaction notes

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