Hydrochloric Acid → Abemaciclib Metabolites M2

HRID 2264367Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264367
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[N:17][C:18]([NH:21][C:22]3[N:27]=[C:26]([C:28]4[CH:40]=[C:39]([F:41])[C:31]5[N:32]=[C:33]([CH3:38])[N:34]([CH:35]([CH3:37])[CH3:36])[C:30]=5[CH:29]=4)[C:25]([F:42])=[CH:24][N:23]=3)=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.CO.O1CCOCC1>[F:42][C:25]1[C:26]([C:28]2[CH:40]=[C:39]([F:41])[C:31]3[N:32]=[C:33]([CH3:38])[N:34]([CH:35]([CH3:37])[CH3:36])[C:30]=3[CH:29]=2)=[N:27][C:22]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([CH2:14][N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:16][N:17]=2)=[N:23][CH:24]=1

Komponenten

6

Edukt 2

HCID 313Hydrochloric AcidHCID 67427599HCID 67427599, Verbindung

Produkt 1

HCID 59376686Abemaciclib Metabolites M2Ausbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a mixture of 4-{6-[5-fluoro-4-(7-fluoro-3-isopropyl-2-methyl-3H-benzoimidazol-5-yl)-pyrimidin-2-ylamino]-pyridin-3-ylmethyl}-piperazine-1-carboxylic acid tert-butyl ester (150 mg) in DCM (10 mL) and methanol (10 mL) add hydrogen chloride 4M in dioxane (194 μL). Stir 10 min and remove the solvent under vacuum. Purify by strong cation exchange cartridge (SCX) eluting with methanol and then methanol-NH3 2M followed by silica gel column chromatography eluting with DCM/methanol-NH3 2M (3%) to afford 120 mg of the title compound. MS (ES+): m/z=479 (M+H)+.

Aufarbeitung

  1. customremove the solvent under vacuum
  2. customPurify by strong cation exchange cartridge (SCX)
  3. washeluting with methanol
  4. washeluting with DCM/methanol-NH3 2M (3%)

Quellen und Nachweise

ORD-Eintrag
ord-4192ad56d6ec4fa8bd8794184532c1fa
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855211B2

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