Water → HCID 46182258, Verbindung

HRID 450582

Reaktionsgleichung

Reaktionsgleichung von HRID 450582
C[C:2]1[N:3]=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[O:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[C:5]2[C:10]([CH3:11])=[C:9]([C:12]([NH2:14])=[O:13])[S:8][C:6]=2[N:7]=1.CCN(C(C)C)C(C)C.Cl[CH2:40][C:41]1[N:45]=[CH:44][O:43][N:42]=1.O>CN(C=O)C>[O:43]1[CH:44]=[N:45][C:41]([CH2:40][N:27]2[CH2:28][CH2:29][CH:24]([O:23][C:17]3[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=3[NH:15][C:4]3[C:5]4[C:10]([CH3:11])=[C:9]([C:12]([NH2:14])=[O:13])[S:8][C:6]=4[N:7]=[CH:2][N:3]=3)[CH2:25][CH2:26]2)=[N:42]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27357653-(Chloromethyl)-1,2,4-oxadiazoleHCID 69669337HCID 69669337, Verbindung

Produkt 1

HCID 46182258HCID 46182258, VerbindungAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a suspension of methyl 4-(4-fluoro-2-(piperidin-4-yloxy)phenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxamide (0.06 g, 0.15 mmol) in DMF (2.0 mL) was added Hünigs base (0.06 mL, 0.35 mmol) and 3-(chloromethyl)-1,2,4-oxadiazole (0.035 g, 0.3 mmol) and the mixture was warmed to 60° C. for 18 hours. After cooling to ambient temperature water (2 mL) was added and the mixture stirred for 0.5 hours. The precipitated solid was collected by filtration and triturated from boiling MeCN. The solid was collected by filtration and dried under vacuum to give beige solid (0.046 g, 63%).

Aufarbeitung

  1. additionwas added
  2. filtrationThe precipitated solid was collected by filtration
  3. customtriturated
  4. filtrationThe solid was collected by filtration
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f65ee6a7b4204ab6971f068f7683a86d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486953B2

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