Hydrochloric Acid → 2-(4-(4-chloropyrimidin-2-ylamino)-1H-pyrazol-1-yl)-N-isopropylacetamide

HRID 929911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929911
O[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH2:14][C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH:13]=2)[N:3]=1.Cl.O1CCOCC1.O=P(Cl)(Cl)[Cl:30]>C(#N)C>[Cl:30][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH2:14][C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH:13]=2)[N:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 312751,4-DioxaneHCID 178457882HCID 178457882, Verbindung

Produkt 1

HCID 900240272-(4-(4-chloropyrimidin-2-ylamino)-1H-pyrazol-1-yl)-N-isopropylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of 2-(4-(4-hydroxypyrimidin-2-ylamino)-1H-pyrazol-1-yl)-N-isopropylacetamide (6.0 g, 22 mmol) in acetonitrile (300 mL) was added 4M HCl in dioxane (12 mL, 48 mmol) then POCl3 (10 g). The mixture was heated to reflux for 0.5 h then concentrated in vacuo. The residue was slurried with water and adjusted to pH 9 with aqueous sodium hydrogen carbonate. The remaining solid was collected by filtration and purified by column chromatography (50% v/v DCM/ethyl acetate) to afford 2-(4-(4-chloropyrimidin-2-ylamino)-1H-pyrazol-1-yl)-N-isopropylacetamide II-1 (2.30 g, 36%) as a white solid. LC-MS (Method A), RT=8.28 min. (ES+) 295.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 0.5 h
  3. concentrationthen concentrated in vacuo
  4. filtrationThe remaining solid was collected by filtration
  5. custompurified by column chromatography (50% v/v DCM/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5ea791708718482c9a2b365a9070ff73
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296725B2

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