Potassium Iodide → HCID 58777653, Verbindung

HRID 1371738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371738
[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]N3CCCC3)(=[O:28])=[O:27])[CH2:22][CH2:21]2)[N:3]=1.[I-].[K+].[C:39]([O-:42])(=[O:41])[CH3:40].[K+]>CN(C)C=O.O.[Cl-].[Na+]>[NH2:1][C:2]1[C:7]([C:8](=[O:9])[C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[CH:6][N:5]=[C:4]([NH:19][CH:20]2[CH2:21][CH2:22][N:23]([S:26]([CH2:29][CH2:30][CH2:31][O:42][C:39](=[O:41])[CH3:40])(=[O:28])=[O:27])[CH2:24][CH2:25]2)[N:3]=1

Komponenten

7

Edukt 3

HCID 4875Potassium IodideHCID 517044Potassium AcetateHCID 10414333HCID 10414333, Verbindung

Produkt 1

HCID 58777653HCID 58777653, VerbindungAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 5234Sodium ChlorideLösungsmittelHCID 6228DimethylformamideLösungsmittel

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 273), potassium iodide (100 mg, 0.61 mmol), and potassium acetate (120 mg, 1.22 mmol) in dimethylformamide (6 mL) was heated at 65–85° C. under nitrogen for 14 hours. The resulting solution was diluted with 50 mL of cold water plus 20 mL of saturated aqueous sodium chloride. Solids were filtered, collected and dissolved in methylene chloride. After washing with water, the organic layer was separated and dried (Na2SO4). The residue was purified by silica gel chromatography (ethyl acetate/hexane) and crystallized from methylene chloride/ethyl ether to give acetic acid 3-[4-[4-amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-sulfonyl]-propyl ester as a white solid (42 mg, 51% yield). HRMS, observed: 510.1822; Calcd for (M+H)+: 510.1817

Aufarbeitung

  1. temperaturewas heated at 65–85° C. under nitrogen for 14 hours
  2. filtrationSolids were filtered
  3. customcollected
  4. dissolutiondissolved in methylene chloride
  5. washAfter washing with water
  6. customthe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customThe residue was purified by silica gel chromatography (ethyl acetate/hexane)
  9. customcrystallized from methylene chloride/ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1e5871fad24e41c29bdbcfa94c21ef73
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157455B2

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