N,N-Dimethylglycine → 1-[4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidino]-2-(dimethylamino)-1-ethanone

HRID 432371

Reaktionsgleichung

Reaktionsgleichung von HRID 432371
Cl.Cl.[I:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[N:10][C:11]=2[NH2:13])[N:6]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[N:5]=1.[CH3:20][N:21]([CH3:26])[CH2:22][C:23](O)=[O:24].ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(NC(C)C)C>ClCCl>[NH2:13][C:11]1[N:10]=[CH:9][N:8]=[C:7]2[N:6]([CH:14]3[CH2:19][CH2:18][N:17]([C:23](=[O:24])[CH2:22][N:21]([CH3:26])[CH3:20])[CH2:16][CH2:15]3)[N:5]=[C:4]([I:3])[C:12]=12

Komponenten

7

Edukt 5

HCID 673N,N-DimethylglycineHCID 88318IsopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 223473623-iodo-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine dihydrochloride

Produkt 1

HCID 223472841-[4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidino]-2-(dimethylamino)-1-ethanoneAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3-Iodo-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine dihydrochloride salt (3 g, 7.19 mmol) was suspended in dichloromethane (350 mL) then N,N-dimethyl glycine (1.02 g, 9.88 mmol), 1-hydroxy-7-azabenzotriazole (1.08 g, 7.91 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.89 g, 9.89 mmol), and N-ethyl-N-isopropylamine (5.06 g, 39.2 mmol) were added over 4 days. The reaction was diluted with dichloromethane (300 mL) then washed with water (150 mL) and brine (150 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 1-[4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidino]-2-(dimethylamino)-1-ethanone as a tan solid (2.74 g, 6.39 mmol). HPLC-RT: 7.40 min. (flow rate: 1 mL/min λ=254 nm Gradient: 5% to 85% acetonitrile/0.1M aqueous ammonium acetate gradient over 20 min.; Deltapak C18, 300 Å, 5 μm, 150×3.9 mm column); m/z (MH+)=430.3.

Aufarbeitung

  1. washthen washed with water (150 mL) and brine (150 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-762158c7fef44979b5b5f9b5589e421c
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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