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Stannanecarbonitrile, tributyl- → (2,5-Dimorpholinopyridin-3-ylamino)-3-methyl-2-(pyridin-2-yl)quinoline-8-carbonitrile

HRID 1431537
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1431537
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[C:8]([CH3:18])=[C:7]2[NH:19][C:20]1[C:21]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[N:22][CH:23]=[C:24]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:25]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C([Sn]([C:85]#[N:86])(CCCC)CCCC)CCC>CN1CCCC1=O.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.[Pd+2]>[O:35]1[CH2:34][CH2:33][N:32]([C:21]2[C:20]([NH:19][C:7]3[C:6]4[C:11](=[C:2]([C:85]#[N:86])[CH:3]=[CH:4][CH:5]=4)[N:10]=[C:9]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=4)[C:8]=3[CH3:18])=[CH:25][C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:23][N:22]=2)[CH2:37][CH2:36]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 200512Stannanecarbonitrile, tributyl-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl2×HCID 596314868-chloro-N-(2,5-dimorpholinopyridin-3-yl)-3-methyl-2-(pyridin-2-yl)quinolin-4-amine

Produkt 1

HCID 59631330(2,5-Dimorpholinopyridin-3-ylamino)-3-methyl-2-(pyridin-2-yl)quinoline-8-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2733347
Palladium(II) trifluoroacetate
Katalysator
2×
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a stirred solution of 8-chloro-N-(2,5-dimorpholinopyridin-3-yl)-3-methyl-2-(pyridin-2-yl)quinolin-4-amine (0.180 g, 0.35 mmol) in 1-methylpyrrolidin-2-one (3.46 mL) was added palladium bis(trifluoroacetate) (0.017 g, 0.052 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropyl-biphenyl (0.050 g, 0.11 mmol) followed by tri-n-butyltin cyanide (0.109 g, 0.35 mmol). The reaction was heated to 160° C. for 36 h. A further 0.3 eq of palladium bis(trifluoroacetate) and 0.6 eq of dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine was added. The reaction was further heated at 160° C. for 3 h. After which, the reaction was cooled to 23° C. The crude product was filtered through a plug of alumina eluting with EtOAc. The organic layer was washed with water, dried over MgSO4 and filtered and evaporated in vacuo. The crude product was purified by column chromatography on alumina (0 to 50% EtOAc/hexane)) to give the desired product 4-((2,5-dimorpholinopyridin-3-ylamino)-3-methyl-2-(pyridin-2-yl)quinoline-8-carbonitrile. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.72 (1H, ddd, J=4.8, 1.8, 1.0 Hz), 8.29 (1H, dd, J=7.1, 1.3 Hz), 8.19 (1H, dd, J=8.5, 1.3 Hz), 8.03-8.08 (2H, m), 7.96 (1H, dt, J=7.9, 1.1 Hz), 7.61-7.65 (2H, m), 7.53 (1H, ddd, J=7.6, 4.8, 1.3 Hz), 6.55 (1H, d, J=2.7 Hz), 3.65 (4H, m), 3.39 (4H, m), 2.95 (4H, m), 2.88 (4H, m), 2.19 (3H, s). Mass Spectrum (ESI) m/e=508.3 (M+1).

Aufarbeitung

  1. temperatureThe reaction was further heated at 160° C. for 3 h
  2. temperatureAfter which, the reaction was cooled to 23° C
  3. filtrationThe crude product was filtered through a plug of alumina eluting with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe crude product was purified by column chromatography on alumina (0 to 50% EtOAc/hexane))

Quellen und Nachweise

ORD-Eintrag
ord-50c97e3a8c554dfcaa08cc446da7a903
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08940724B2

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