Dimethylformamide → HCID 178440306, Verbindung

HRID 1625235

Reaktionsgleichung

Reaktionsgleichung von HRID 1625235
[CH:1]1[NH:8][C:6](=[O:7])[NH:5][C:3](=[O:4])[C:2]=1C(O)=O.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH:35]([C:38]1[C:46]2[C:41](=[N:42][CH:43]=[CH:44][C:45]=2[C:47]2[CH:48]=[N:49][C:50]3[C:55]([CH:56]=2)=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:40]([C:57]2[CH:64]=[CH:63][C:60]([C:61]#[N:62])=[C:59]([NH:65][CH:66]3[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]3)[CH:58]=2)[N:39]=1)([CH3:37])[CH3:36].CN([CH:75]=[O:76])C>O.C(OCC)(=O)C>[OH:7][C:6]1[N:8]=[C:1]([C:75]([N:69]2[CH2:68][CH2:67][CH:66]([NH:65][C:59]3[CH:58]=[C:57]([N:40]4[C:41]5=[N:42][CH:43]=[CH:44][C:45]([C:47]6[CH:48]=[N:49][C:50]7[C:55]([CH:56]=6)=[CH:54][CH:53]=[CH:52][CH:51]=7)=[C:46]5[C:38]([CH:35]([CH3:37])[CH3:36])=[N:39]4)[CH:64]=[CH:63][C:60]=3[C:61]#[N:62])[CH2:71][CH2:70]2)=[O:76])[CH:2]=[C:3]([OH:4])[N:5]=1

Komponenten

8

Edukt 5

HCID 6228DimethylformamideHCID 903011,2,3,4-Tetrahydro-2,4-dioxo-5-pyrimidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 675014474-{3-Isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-2-(piperidin-4-ylamino)benzonitrile

Produkt 1

HCID 178440306HCID 178440306, VerbindungAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Isoorotic acid (0.021 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.029 g), and 1-hydroxybenzotriazole monohydrate (0.016 g) were added to a solution of compound (77a) (0.050 g) in DMF (1.0 mL), followed by stirring under argon flow at room temperature for 15 hr. The reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and the solvent was distilled away to obtain 2-{1-(2,6-dihydroxypyrimidine-4-carbonyl)piperidin-4-ylamino}-4-{3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile, which was used in the subsequent reaction without being purified. According to Example 1(7), compound (78) (0.026 g, the second stage yield: 39%) was prepared as a white solid using 2-{1-(2,6-dihydroxypyrimidine-4-carbonyl)piperidin-4-ylamino}-4-{3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile instead of compound (1f).

Aufarbeitung

  1. washthe organic layer was washed with saturated saline
  2. dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled away

Quellen und Nachweise

ORD-Eintrag
ord-8cca2535026f4100835c785f066ac0cd
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08779142B2

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