Potassium Iodide → HCID 58777598, Verbindung

HRID 1435319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435319
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([S:26]([CH2:29][CH2:30][CH2:31]Cl)(=[O:28])=[O:27])[CH2:22][CH2:21]2)[N:3]=1.[I-].[K+].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>O1CCOCC1.O.[Cl-].[Na+]>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([S:26]([CH2:29][CH2:30][CH2:31][N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)(=[O:28])=[O:27])[CH2:22][CH2:21]2)[N:3]=1

Komponenten

7

Edukt 3

HCID 4875Potassium IodideHCID 8083MorpholineHCID 10458099[4-Amino-2-[1-(3-chloro-propane-1-sulfonyl)-piperidin-4-ylamino]-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone

Produkt 1

HCID 58777598HCID 58777598, VerbindungAusbeute 17,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 5234Sodium ChlorideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A suspension of [4-amino-2-[1-(3-chloro-propane-1-sulfonyl)-piperidin-4-ylamino]-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone (80 mg, 0.16 mmol, Example 272), potassium iodide (200 mg, 1.2 mmol), morpholine (200 mg, 4.3 mmol) in dioxane (12 mL) was heated at reflux under nitrogen for 48 hours. The resulting solution was diluted with 20 mL of cold water plus 20 mL of saturated aqueous sodium chloride. Solids were filtered and dissolved in methylene chloride. The organic layer was separated and dried (Na2SO4). The residue was purified by silica gel chromatography (triethylamine/methanol/methylene chloride 1:10:90) and crystallized from methylene chloride/hexane to give [4-amino-2-[1-(3-morpholin-4-yl-propane-1-sulfonyl)-piperidin-4-ylamino]-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone as a white solid (15 mg, 17% yield). HRMS, observed: 537.2296; Calcd for (M+H)+: 537.2290

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 48 hours
  3. filtrationSolids were filtered
  4. dissolutiondissolved in methylene chloride
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customThe residue was purified by silica gel chromatography (triethylamine/methanol/methylene chloride 1:10:90)
  8. customcrystallized from methylene chloride/hexane

Quellen und Nachweise

ORD-Eintrag
ord-c47322391f2940cea7d142fa8a5275e9
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07615634B2

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