Diethyl Ether → (2,5-Difluoro-benzyl)-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-6'-yl)-amine hydrochloride salt

HRID 2182165

Reaktionsgleichung

Reaktionsgleichung von HRID 2182165
C(OC(=O)[N:7]([CH2:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[F:28])[C:8]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:11]=[N:10][CH:9]=1)(C)(C)C.[ClH:30].CCOCC.C(OCC)C>CO.Cl>[ClH:30].[F:28][C:22]1[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=1[CH2:20][NH:7][C:8]1[N:13]=[C:12]([N:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)[CH:11]=[N:10][CH:9]=1

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 10953452Ether hydrochloride2×HCID 69730478(2,5-difluoro-benzyl)-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-6'-yl)-carbamic acid tert-butyl ester

Produkt 1

HCID 22481974(2,5-Difluoro-benzyl)-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-6'-yl)-amine hydrochloride saltAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

The general procedure described in Example 4-A was followed using 2,5-difluoro-benzylamine as the amine in the preparation of the first intermediate and DMAP (1 equiv.) to give the BOC-protected compound. The protecting group was removed by dissolving (2,5-difluoro-benzyl)-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-6′-yl)-carbamic acid tert-butyl ester (99.6 mg, 0.24 mmol) in methanol (1 mL) and treating it with 1.0M HCl/Ether (3.68 mL, 3.68 mmol) and stirring the reaction mixture overnight at ambient temperature. Additional 1.0M HCl/ether (2 mL) was added to the reaction mixture and stirring continued overnight at room temperature. The reaction was still not complete, therefore conc. HCl (2 drops) was added and the resulting mixture stirred at ambient temperature overnight. Diethyl ether (20 mL) was added to the reaction mixture and stirring continued for 1 h. The solids were filtered from the reaction mixture, washed with Ether, and dried under high vacuum to give the title compound 4-P (64 mg).

Aufarbeitung

  1. customThe protecting group was removed
  2. stirringstirring continued overnight at room temperature
  3. stirringthe resulting mixture stirred at ambient temperature overnight
  4. stirringstirring
  5. waitcontinued for 1 h
  6. filtrationThe solids were filtered from the reaction mixture
  7. washwashed with Ether
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e5c932272e62468baa401205df97b644
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894050B2

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