Benzoic Acid → Linagliptin benzoate

HRID 1626299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626299
[CH3:1][C:2]#[C:3][CH2:4][N:5]1[C:9]([N:10]2[CH2:15][C@H:14]([NH2:16])[CH2:13][CH2:12][CH2:11]2)=[N:8][C:7]2[N:17]([CH3:35])[C:18]([N:20]([CH2:23][C:24]3[N:25]=[C:26]([CH3:34])[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=4[N:33]=3)[C:21](=[O:22])[C:6]1=2)=[O:19].[C:36]([OH:44])(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(O)(C)C>[CH3:1][C:2]#[C:3][CH2:4][N:5]1[C:9]([N:10]2[CH2:15][C@H:14]([NH2:16])[CH2:13][CH2:12][CH2:11]2)=[N:8][C:7]2[N:17]([CH3:35])[C:18]([N:20]([CH2:23][C:24]3[N:25]=[C:26]([CH3:34])[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=4[N:33]=3)[C:21](=[O:22])[C:6]1=2)=[O:19].[C:36]([O-:44])(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Komponenten

4

Edukt 2

HCID 243Benzoic AcidHCID 10096344Linagliptin

Produkt 1

HCID 131731672Linagliptin benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of 2.50 g Linagliptin free base in 20 ml isopropanol was heated to reflux. To the hot suspension 646 mg benzoic acid dissolved in 5 ml isopropanol were added. The mixture was allowed to cool to about 25° C. and further stirred at the same temperature for about 7.5 hours. The solid was isolated by filtration and dried at 40° C. for about 13 hours to obtain 2.94 g crystalline Linagliptin benzoate of WO2010/072776 A1, which was confirmed to be Linagliptin benzoate form I by XRPD.

Aufarbeitung

  1. temperaturewas heated to reflux
  2. additionwere added
  3. customThe solid was isolated by filtration
  4. customdried at 40° C. for about 13 hours

Quellen und Nachweise

ORD-Eintrag
ord-54e40f1cc128482eba06041c8e585f9f
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785455B2

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