Potassium Iodide → HCID 10414333, Verbindung

HRID 1371737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371737
[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[CH2:39][CH2:38][CH2:37][CH2:36]1>O1CCOCC1>[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[CH2:39][CH2:38][CH2:37][CH2:36]3)(=[O:28])=[O:27])[CH2:22][CH2:21]2)[N:3]=1

Komponenten

5

Edukt 3

HCID 4875Potassium IodideHCID 31268PyrrolidineHCID 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 10414333HCID 10414333, VerbindungAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °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 (25 mg, 0.051 mmol, Example 272), potassium iodide (30 mg, 0.18 mmol), and pyrollidine (400 mg, 5.6 mmol) in dioxane (8 mL) was heated at 90° C. under nitrogen for 14 hours. The resulting solution was concentrated to ˜1 mL and triturated with water. Solids were filtered and dissolved in methylene chloride. After washing with water, the organic layer was separated and dried (Na2SO4). The product was purified by trituration with tetrahydrofuran/ethyl ether and filtered to give [4-amino-2-[1-(3-pyrrolidin-1-yl-propane-1-sulfonyl)-piperidin-4-ylamino]-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone as a white solid (12 mg, 40% yield). HRMS, observed: 521.2343; Calcd for (M+H)+: 521.2341

Aufarbeitung

  1. concentrationThe resulting solution was concentrated to ˜1 mL
  2. customtriturated with water
  3. filtrationSolids were filtered
  4. dissolutiondissolved in methylene chloride
  5. washAfter washing with water
  6. customthe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customThe product was purified by trituration with tetrahydrofuran/ethyl ether
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-218632e5d676412491d08538f4fce59c
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157455B2

Notizen zur Reaktion

Wird geladen…