Cesium carbonate → N-(3-(2-(6-(4-Ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide

HRID 2042212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2042212
Cl[C:2]1[N:3]=[CH:4][C:5]2[S:10][CH:9]=[C:8]([C:11]3[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=3)[C:6]=2[N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:28]([N:30]1[CH2:35][CH2:34][N:33]([C:36]2[N:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=2)[CH2:32][CH2:31]1)[CH3:29].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:28]([N:30]1[CH2:31][CH2:32][N:33]([C:36]2[N:41]=[CH:40][C:39]([NH:42][C:2]3[N:3]=[CH:4][C:5]4[S:10][CH:9]=[C:8]([C:11]5[CH:12]=[C:13]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[CH:15][CH:16]=5)[C:6]=4[N:7]=3)=[CH:38][CH:37]=2)[CH2:34][CH2:35]1)[CH3:29]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 91616746-(4-Ethylpiperazin-1-yl)pyridin-3-amineHCID 86673215N-(3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide

Produkt 1

HCID 51347359N-(3-(2-(6-(4-Ethylpiperazin-1-yl)pyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamideAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

N-(3-(2-chlorothieno[3,2-d]pyrimidin-7-yl)phenyl)methanesulfonamide (20 mg, 0.059 mmol) was dissolved in dioxane (1 mL) and then cesium carbonate (58 mg, 0.18 mmol) and 6-(4-ethylpiperazin-1-yl)pyridin-3-amine (18 mg, 0.088 mmol) were added. After flowing nitrogen gas to the reaction mixture for 10 minutes, Pd(OAc)2 (1 mg, 0.1 mmol) and Xantphos (4 mg, 0.12 mmol) were added. The reaction mixture was stirred at 120° C. for 6 hours and filtered with celite. The filtrate was diluted with ethyl acetate and washed with brine. The organic layer was dried with magnesium sulfate and concentrated by filtering with celite. Purification by chromatography (5% methanol/dichloromethane) yielded the target compound (16 mg, 53% yield).

Aufarbeitung

  1. customfor 10 minutes
  2. filtrationfiltered with celite
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated
  7. filtrationby filtering with celite
  8. customPurification by chromatography (5% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-e0adc1e09bfc4e7f950a9c97ea28c021
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586580B2

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