Methanol → 4-Chloro-2-(4-cyclobutyl-piperazin-1-yl)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1172522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172522
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.Cl[CH2:7][CH2:8][N:9]([CH2:32][CH2:33]Cl)[C:10]1[CH:30]=[C:29]([Cl:31])[C:13]2[O:14][C:15]3[C:24]([CH3:25])=[CH:23][C:22]([C:26]([OH:28])=[O:27])=[CH:21][C:16]=3[S:17](=[O:20])(=[O:19])[CH2:18][C:12]=2[CH:11]=1.[CH3:35]O>>[CH3:35][O:28][C:26]([C:22]1[CH:23]=[C:24]([CH3:25])[C:15]2[O:14][C:13]3[C:29]([Cl:31])=[CH:30][C:10]([N:9]4[CH2:8][CH2:7][N:5]([CH:1]5[CH2:4][CH2:3][CH2:2]5)[CH2:33][CH2:32]4)=[CH:11][C:12]=3[CH2:18][S:17](=[O:20])(=[O:19])[C:16]=2[CH:21]=1)=[O:27]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 75645CyclobutylamineHCID 1317284742-[Bis-(2-chloroethyl)amino]-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]-cycloheptene-8-carboxylic acid

Produkt 1

HCID 1317284924-Chloro-2-(4-cyclobutyl-piperazin-1-yl)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Cyclobutylamine (1 mL, excess) was added to a solution of Example 102j (0.6 g, 1.25 mmol) in methanol (10 mL), followed by the addition of n-tetrabutylammonium iodide (0.01 g, 0.027 mmol) in an atmosphere of nitrogen and sealed in a pressure reactor vessel at 110° C. for 6 h. It was brought to room temperature, concentrated, treated with methanolic HCl solution, and refluxed at 70° C. for 6 h. The reaction mixture was concentrated, treated with water, aqueous sodium bicarbonate solution to neutral pH and the solid that separated was washed with water dried, and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as a white solid. Yield: 0.410 g, (25%); 1H NMR (DMSO-d6): δ 1.60-2.10 (m, 6H, 3CH2), 2.40-2.50 (m, 4H, 2CH2), 2.80 (m, 1H, CH), 3.20-3.30 (m, 4H, 2CH2), 3.90 (s, 3H, OCH3), 4.70 (s, 2H, CH2), 6.80 (s, 1H, Ar), 6.90 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.50 (s, 1H, Ar); MS: m/e (CI+) 491 (M+1).

Aufarbeitung

  1. customsealed in a pressure reactor vessel at 110° C. for 6 h
  2. customwas brought to room temperature
  3. concentrationconcentrated
  4. additiontreated with methanolic HCl solution
  5. concentrationThe reaction mixture was concentrated
  6. additiontreated with water, aqueous sodium bicarbonate solution to neutral pH
  7. customthe solid that separated
  8. washwas washed with water
  9. customdried
  10. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-643b17d2173a4e5e98844e647e9ab659
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834001B2

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