Butyric Acid → [4-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-butyramide

HRID 655850

Reaktionsgleichung

Reaktionsgleichung von HRID 655850
N[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3=[N:13][CH:14]=[N:15][C:16]([NH2:17])=[C:11]3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[C:18]([OH:23])(=O)[CH2:19][CH2:20][CH3:21].Cl.C[N:26](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C.CO>[NH2:17][C:16]1[N:15]=[CH:14][N:13]=[C:12]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([CH:19]([CH2:20][CH3:21])[C:18]([NH2:26])=[O:23])=[CH:3][CH:4]=3)[N:9]=[CH:10][C:11]=12

Komponenten

7

Edukt 4

HCID 264Butyric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 119959601-(4-Amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine

Produkt 1

HCID 131729304[4-(4-Amino-pyrazolo[3,4-d]pyrimidin-1-yl)-phenyl]-butyramideAusbeute 19,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Title compound 11A, 1-(4-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (38 mg, 1.1 eq, 0.17 mmol) was added to a solution of butyric acid (13 mg, 1.0 eq, 0.15 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26 mg, 1.1 eq, 0.17 mmol), 1-hydroxybenzotriazole (21 mg, 1.0 eq, 0.15 mmol) in DMF (1 ml) which had been stirred for 10 minutes under an inert atmosphere. The reaction was stirred at room temperature for 18 hours, after which methanol (1 ml) was added and the solvents were removed in vacuo. The resultant solid purified by semi-preparative HPLC to yield the title compound as a white solid (8.5 mg, 0.029 mmol, 19%). LCMS: [M+H]+=297, Rt=1.45 min, 100% purity.

Aufarbeitung

  1. stirringThe reaction was stirred at room temperature for 18 hours
  2. customthe solvents were removed in vacuo
  3. customThe resultant solid purified by semi-preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-dafc2ac356984b20b9b2bb4c5534eee8
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071607B2

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