Acetic Acid → HCID 58777639, Verbindung

HRID 1371739Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371739
[NH2:1][C:2]1[C:7]([C:8](=[O:18])[C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])=[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][O:32]C(=O)C)(=[O:28])=[O:27])[CH2:22][CH2:21]2)[N:3]=1.[OH-].[K+].C(O)C.C(O)(=O)C>O>[NH2:1][C:2]1[C:7]([C:8]([C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])=[O:18])=[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][OH:32])(=[O:28])=[O:27])[CH2:22][CH2:21]2)[N:3]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 58777653HCID 58777653, Verbindung

Produkt 1

HCID 58777639HCID 58777639, VerbindungAusbeute 52,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A suspension of acetic acid 3-[4-[4-amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-sulfonyl]-propyl ester (25 mg, 0.049 mmol, Example 274) in a solution of potassium hydroxide (50 mg, 0.9 mmol), water (1 mL) and ethanol (6 mL) was stirred at 25° C. for 1 hour. The solution was cooled, acidified with acetic acid and reduced in volume to 2 mL. This was diluted with water and the product extracted into methylene chloride. After washing with water, the organic layer was separated and dried (Na2SO4). The residue was purified by silica gel chromatography (ethyl acetate) and crystallized from methylene chloride/hexane to give [4-amino-2-[1-(3-hydroxy-propane-1-sulfonyl)-piperidin-4-ylamino]-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanoneas a white solid (12 mg, 50% yield). HRMS, observed: 468.1716; Calcd for (M+H)+: 468.1712

Aufarbeitung

  1. temperatureThe solution was cooled
  2. extractionthe product extracted into methylene chloride
  3. washAfter washing with water
  4. customthe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customThe residue was purified by silica gel chromatography (ethyl acetate)
  7. customcrystallized from methylene chloride/hexane

Quellen und Nachweise

ORD-Eintrag
ord-fed20fa9549441a791c3709d4fde659d
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157455B2

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