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

HRID 1927492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927492
[CH3:1][NH2:2].C[O:4][C:5]([C:7]1[CH:8]=[C:9]([CH3:32])[C:10]2[O:16][C:15]3[C:17]([Cl:28])=[CH:18][C:19]([N:21]([CH2:25][CH2:26]Cl)[CH2:22][CH2:23]Cl)=[CH:20][C:14]=3[CH2:13][S:12](=[O:30])(=[O:29])[C:11]=2[CH:31]=1)=[O:6]>CO>[Cl:28][C:17]1[C:15]2[O:16][C:10]3[C:9]([CH3:32])=[CH:8][C:7]([C:5]([OH:4])=[O:6])=[CH:31][C:11]=3[S:12](=[O:29])(=[O:30])[CH2:13][C:14]=2[CH:20]=[C:19]([N:21]2[CH2:22][CH2:23][N:2]([CH3:1])[CH2:26][CH2:25]2)[CH:18]=1

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 115260722-[Bis-(2-chloro-ethyl)-amino]-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Produkt 1

HCID 1317284754-Chloro-6-methyl-2-(4-methyl-piperazin-1-yl)-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Methanolic methylamine solution (20% v/v, 6 mL) was added to a solution of Example 102 (0.330 g, 0.69 mmol) in methanol (2 mL) in an atmosphere of nitrogen and sealed in a pressure reactor vessel at 100° C. for 6 h. It was brought to room temperature, flushed with N2 gas, treated with chilled water and dilute HCl to neutral pH. The solid that precipitated was filtered, washed with water, dried and purified using flash chromatography (silica gel, MeOH/CHCl3) to obtain the title compound as an off white solid. Yield: 0.260 g (86.37%). 1H NMR (DMSO-d6): δ 2.40 (s, 3H, CH3), 2.70 (s, 3H, CH3), 2.72-2.75 (m, 4H, 2CH2), 3.30-3.35 (m, 4H, 2CH2), 5.10 (s, 2H, CH2), 7.10 (s, 1H, Ar), 7.20 (s, 1H, Ar), 8.10 (s, 1H, Ar) and 8.25 (s, 1H, Ar); MS: m/e (ES+) 436 (M+1).

Aufarbeitung

  1. customsealed in a pressure reactor vessel at 100° C. for 6 h
  2. customwas brought to room temperature
  3. customflushed with N2 gas
  4. additiontreated with chilled water and dilute HCl to neutral pH
  5. customThe solid that precipitated
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried
  9. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-f0ea493291a84ebcb9e00bca1285d7a3
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183234B2

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