Triethylamine → 4-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonate

HRID 336140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336140
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[NH2:13][C:14]1[C:19]2[C:20]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:21]3[N:26]([C:18]=2[N:17]=[CH:16][N:15]=1)[CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]3.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:8][S:9]([O:27][CH:24]1[CH2:23][CH2:22][C:21]2[N:26]([C:18]3[N:17]=[CH:16][N:15]=[C:14]([NH2:13])[C:19]=3[C:20]=2[C:28]2[CH:29]=[N:30][C:31]3[C:36]([CH:37]=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:25]1)(=[O:11])=[O:10]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 867112804-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-ol

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (0.157 ml) and methanesulfonyl chloride (0.074 ml) were added to a solution of 4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-ol (288 mg) obtained in Step 8 in THF (5 ml) under ice-cooling. After stirring at the same temperature for 15 minutes, the mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a light-brown solid (615 mg).

Aufarbeitung

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e0b5e9bdad224a43b4cb5056569659b7
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889666B2

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