1-Methoxy-2-propanol → 5-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1-methyl-1,3-dihydro-indol-2-one

HRID 1262022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1262022
CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)[N:6]2[N:5]=1)=O.C(N(CC)C(C)C)(C)C.[NH2:30][C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[N:36]([CH3:40])[C:35](=[O:41])[CH2:34]2.COCC(O)C>>[CH3:20][O:19][C:16]1[N:15]=[CH:14][C:13]([C:12]2[N:6]3[C:7]([CH:8]=[N:9][C:4]([NH:30][C:31]4[CH:32]=[C:33]5[C:37](=[CH:38][CH:39]=4)[N:36]([CH3:40])[C:35](=[O:41])[CH2:34]5)=[N:5]3)=[CH:10][CH:11]=2)=[CH:18][CH:17]=1

Komponenten

5

Edukt 4

HCID 79001-Methoxy-2-propanolHCID 81531DiisopropylethylamineHCID 226924705-Amino-1-methyl-2-oxoindolineHCID 667108472-Methanesulfinyl-7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazine

Produkt 1

HCID 667116245-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1-methyl-1,3-dihydro-indol-2-oneAusbeute 8,3 %

Versuchsvorschrift

2-Methanesulfinyl-7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazine (125.0 mg, 0.0004335 mol), N,N-Diisopropylethylamine (0.249 mL, 0.00143 mol) and 5-Amino-1-methyl-1,3-dihydro-indol-2-one (0.141 g, 0.000867 mol) were dissolved in 1-Methoxy-2-propanol (0.498 mL, 0.00510 mol) and the reaction was irradiated at 300 watts, 180° C. for 40 minutes or until HPLC showed consumption of starting material. The reaction mixture was then reduced en vacuo and the product was isolated and purified by Gilson prep HPLC to afford 13.85 mg of 5-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1-methyl-1,3-dihydro-indol-2-one as a lyophilized powder. (M+H)=387.1. 1H NMR (400 MHz, DMSO, d6) δ 9.40 (s, 1H), 8.96 (s, 2H), 8.47 (d, 1H, J=8.73 Hz), 7.82 (s, 1H), 7.51 (d, 1H, J=8.40 Hz), 7.16 (d, 1H, J=4.37 Hz), 7.04 (d, 1H, J=8.65 Hz), 6.91 (m, 2H), 3.95 (s, 3H), 3.59 (s, 2H), 3.12 (s, 3H).

Aufarbeitung

  1. customthe reaction was irradiated at 300 watts, 180° C. for 40 minutes or until HPLC
  2. customconsumption of starting material
  3. customthe product was isolated
  4. custompurified by Gilson prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-6fea87fb18fc43f99ea9a04f909754dc
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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