4-Chlorothieno[2,3-d]pyrimidine → 1-(4-(2-(3-Phenoxy-5-(thieno[2,3-d]pyrimidin-4-ylthio)pyridin-2-ylamino)thiazol-4-yl)piperidin-yl)ethanone

HRID 1806181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1806181
Cl[C:2]1[C:3]2[CH:10]=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:11]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[N:21]=[C:22]([NH:25][C:26]3[N:31]=[CH:30][C:29]([S:32]CCC(OC)=O)=[CH:28][C:27]=3[O:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[S:23][CH:24]=2)[CH2:16][CH2:15]1)(=[O:13])[CH3:12].CC([O-])(C)C.[K+]>CS(C)=O>[O:39]([C:27]1[C:26]([NH:25][C:22]2[S:23][CH:24]=[C:20]([CH:17]3[CH2:16][CH2:15][N:14]([C:11](=[O:13])[CH3:12])[CH2:19][CH2:18]3)[N:21]=2)=[N:31][CH:30]=[C:29]([S:32][C:2]2[C:3]3[CH:10]=[CH:9][S:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:28]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Komponenten

5

Edukt 3

HCID 7366184-Chlorothieno[2,3-d]pyrimidineHCID 23665647Potassium tert-butoxideHCID 86631532Methyl 3-(6-(4-(1-acetylpiperidin-4-yl)thiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate

Produkt 1

HCID 577427911-(4-(2-(3-Phenoxy-5-(thieno[2,3-d]pyrimidin-4-ylthio)pyridin-2-ylamino)thiazol-4-yl)piperidin-yl)ethanoneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

4-chlorothieno[2,3-d]pyrimidine (0.050 g, 0.29 mmol) and methyl 3-(6-(4-(1-acetylpiperidin-4-yl)thiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)propanoate (0.15 g, 0.29 mmol) were dissolved in DMSO (3 mL). The solution was degassed for 15 minutes. KOtBu (0.098 g, 0.88 mmol) was added and the reaction stirred at room temperature for two hours. The solution was quenched with water, extracted with dichloromethane, dried, and concentrated. Flash chromatography gave the title compound (0.075, 46%). 1H NMR (400 MHz, CDCl3) δ 1.60-1.72 (m, 2H), 2.08-2.15 (m, 2H), 2.11 (m, 3H), 2.65-2.75 (m, 1H), 2.82-2.93 (m, 1H), 3.15-3.24 (m, 1H), 3.91 (d, 1H), 4.72 (d, 1H), 6.49 (s, 1H), 7.15 (d, 2H), 7.19 (t, 1H), 7.27-7.29 (m, 1H), 7.36-7.42 (m, 3H), 7.53 (d, 1H), 8.27 (d, 1H), 8.68 (s, 1H), 8.81 (s, 1H).

Aufarbeitung

  1. customThe solution was degassed for 15 minutes
  2. customThe solution was quenched with water
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d727a28bbbde4948ab8d07d6eea88f3a
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354540B2

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