Methylamine → N8-methyl-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizine-4,8-diamine

HRID 336145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336145
CS(O[CH:6]1[CH2:14][CH2:13][C:12]2[N:8]([C:9]3[N:28]=[CH:27][N:26]=[C:25]([NH2:29])[C:10]=3[C:11]=2[C:15]2[CH:16]=[N:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:7]1)(=O)=O.[CH3:30][NH2:31]>CO>[CH3:30][NH:31][CH:6]1[CH2:14][CH2:13][C:12]2[N:8]([C:9]3[N:28]=[CH:27][N:26]=[C:25]([NH2:29])[C:10]=3[C:11]=2[C:15]2[CH:16]=[N:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:7]1

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 867112814-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonate

Produkt 1

HCID 86711284N8-methyl-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizine-4,8-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonate (30 mg) obtained in Step 9 of Example 1 was dissolved in a solution of methylamine in 40% methanol (1 ml). The solution was stirred at 60° C. for 1 hour and at 80° C. for 22 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/methanol) to obtain the title compound as a light-yellow, oily substance (8.1 mg).

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-fb009346b62a4df2a2126169493f8ee8
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889666B2

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