Hydrochloric Acid → 1-(2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c][1,8]naphthyridin-4-amine

HRID 1360426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360426
C(OC([NH:8]C1C(B(O)O)=CC=CN=1)=O)(C)(C)C.Cl.C(=O)([O-])[O-].[Na+].[Na+].[CH3:25][CH:26]([CH3:45])[CH2:27][C:28]1[N:29]([CH2:42][CH2:43][CH3:44])[N:30]=[C:31]2[C:40]=1[C:39]1[CH:38]=[CH:37][CH:36]=C[C:34]=1[N:33]=[C:32]2[NH2:41].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CC.C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:25][CH:26]([CH3:45])[CH2:27][C:28]1[N:29]([CH2:42][CH2:43][CH3:44])[N:30]=[C:31]2[C:40]=1[C:39]1[CH:38]=[CH:37][CH:36]=[N:8][C:34]=1[N:33]=[C:32]2[NH2:41]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 112775352H-Pyrazolo[3,4-c]quinolin-4-amine, 1-(2-methylpropyl)-2-propyl-HCID 22135186(2-[(tert-Butoxycarbonyl)amino]pyridin-3-yl)boronic acid

Produkt 1

HCID 577175911-(2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c][1,8]naphthyridin-4-amineAusbeute 11,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 10311-PropanolLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A modification of the method described in Example 16 was used to treat 2-tert-butoxycarbonylamino-3-pyridylboronic acid (11.33 mmol) in 1-propanol (10 mL) with hydrochloric acid (12 mL of 1 M) followed by sodium carbonate (1.99 g, 18.8 mmol), 4-bromo-5-(2-methylpropyl)-1-propyl-1H-pyrazole-3-carbonitrile (1.53 g, 5.66 mmol, prepared as described in Example 1) in 1-propanol (5 mL), triphenylphosphine (44.5 mg, 0.17 mmol), and palladium (II) acetate (13 mg, 0.057 mmol) in toluene (0.25 mL). The reaction was complete after it was heated overnight. Following the work-up procedure and purification, 0.18 g of 1-(2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c][1,8]naphthyridin-4-amine was obtained as off-white needles, mp 257-260° C.

Aufarbeitung

  1. temperaturewas heated overnight
  2. customthe work-up procedure and purification

Quellen und Nachweise

ORD-Eintrag
ord-3f706dc259dc4c449ee751bea2076911
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879849B2

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