Hydrazine hydrate (1:1) → Linagliptin

HRID 530956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530956
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH2:12][N:13]2[C:22](=[O:23])[C:21]3[N:20]([CH2:24][C:25]#[C:26][CH3:27])[C:19]([N:28]4[CH2:33][CH2:32][CH2:31][C@@H:30]([N:34]5C(=O)C6=CC(C)=CC=C6C5=O)[CH2:29]4)=[N:18][C:17]=3[N:16]([CH3:46])[C:14]2=[O:15])[N:3]=1.O.NN>C(O)C>[CH3:27][C:26]#[C:25][CH2:24][N:20]1[C:19]([N:28]2[CH2:29][C@H:30]([NH2:34])[CH2:31][CH2:32][CH2:33]2)=[N:18][C:17]2[N:16]([CH3:46])[C:14]([N:13]([CH2:12][C:4]3[N:3]=[C:2]([CH3:1])[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[N:5]=3)[C:22](=[O:23])[C:21]1=2)=[O:15]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 1317356521-[(4-Methylquinazolin-2-yl)methyl]-3-methyl-7-(2-butin-1-yl)-8-(3(R)-4-methylphthalimidopiperidine-yl)-xanthine

Produkt 1

HCID 10096344Linagliptin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
79 °C

Versuchsvorschrift

In a clean round bottom flask, 9 ml of ethanol, 90 mg of 1-[(4-Methylquinazolin-2-yl)methyl]-3-methyl-7-(2-butin-1-yl)-8-(3-(R)-4-methylphthalimidopiperidin-1-yl)-xanthine & 0.9 ml of hydrazine hydrate were charged. The temperature of the reaction mass was raised to 78-80° C. & the reaction mass was maintained for 3 hours. The reaction mass was cooled to 50° C. & ethanol was distilled off. 9 ml methylene dichloride was added to the obtained residue & stirred at RT to get the solid. Undesired solid was filtered. The filtrate was concentrated & 9 ml methyl tert butyl ether was added to the residue to get the solid Linagliptin. Reaction mass was stirred at RT & filtered. Wet cake was washed with 2 ml IPA. Dry wt 45 mg

Aufarbeitung

  1. temperaturethe reaction mass was maintained for 3 hours
  2. temperatureThe reaction mass was cooled to 50° C.
  3. distillationethanol was distilled off
  4. addition9 ml methylene dichloride was added to the obtained residue
  5. customto get the solid
  6. filtrationUndesired solid was filtered
  7. concentrationThe filtrate was concentrated
  8. addition9 ml methyl tert butyl ether was added to the residue

Quellen und Nachweise

ORD-Eintrag
ord-34b03fe401514054bde76bb756edfacb
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353114B2

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