Trifluoroacetic acid → (3-Chloro-benzyl)-(4-piperazin-1-yl-pyrimidin-2-yl)-amine, hydrochloride

HRID 890569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 890569
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[ClH:28].[Cl:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][NH:20][C:16]1[N:15]=[C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=[CH:18][N:17]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 695961184-[2-(3-Chloro-benzylamino)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 131724680(3-Chloro-benzyl)-(4-piperazin-1-yl-pyrimidin-2-yl)-amine, hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-[2-(3-chloro-benzylamino)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (I-3a) (48.5 mg, 0.12 mmol) in CH2Cl2 (1 mL) was added trifluoroacetic acid (139 μL, 1.8 mmol). After stirring at room temperature for 3 h, the mixture was poured into 1N NaOH (10 mL) and extracted with CH2Cl2 (1×35 mL). The organic layer was washed with brine, dried and concentrated to afford the title compound as a free amine. The free amine in CH2Cl2 (1 mL) was added to 1M HCl in ether (0.10 mL, 0.10 mmol). After stirring for 10 min at room temperature, the solution was concentrated in vacuo to yield the hydrochloride salt (3-A) (32.4 mg) as a yellow solid.

Aufarbeitung

  1. extractionextracted with CH2Cl2 (1×35 mL)
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7edc2e382b824196878fdc7d8960e8d5
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995159B2

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