Potassium Iodide → HCID 58777653, Verbindung

HRID 1435317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435317
[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

Reaktionsbedingungen

Temperatur
75 °C

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. filtrationSolids were filtered
  2. customcollected
  3. dissolutiondissolved in methylene chloride
  4. washAfter washing with water
  5. customthe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/hexane)
  8. customcrystallized from methylene chloride/ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d4361227662d403ab0961cffc9daacd9
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07615634B2

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