Acetic Anhydride → 1-[3-[2-(cyclopropylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-5,6-dihydropyrazolo[1,5-b]pyridazin-7(4H)-yl]ethanone

HRID 2063260Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2063260
[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[C:12]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)=[N:13][N:14]4[C:19]=3[CH2:18][CH2:17][CH2:16][NH:15]4)[CH:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.O>[CH:1]1([NH:4][C:5]2[N:10]=[C:9]([C:11]3[C:12]([C:20]4[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=4)=[N:13][N:14]4[C:19]=3[CH2:18][CH2:17][CH2:16][N:15]4[C:27](=[O:29])[CH3:28])[CH:8]=[CH:7][N:6]=2)[CH2:3][CH2:2]1

Komponenten

6

Edukt 2

HCID 7918Acetic AnhydrideHCID 68514466N-cyclopropyl-4-[2-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-b]pyridazin-3-yl]-2-pyrimidinamine

Produkt 1

HCID 685137641-[3-[2-(cyclopropylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-5,6-dihydropyrazolo[1,5-b]pyridazin-7(4H)-yl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

A catalytic amount of 4-dimethylaminopyridine (ca. 5 mg) was added to a solution of N-cyclopropyl-4-[2-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-b]pyridazin-3-yl]-2-pyrimidinamine (i.e. the product of Step E) (42.1 mg, 0.12 mmol) and acetic anhydride (0.023 mL, 0.24 mmol) in 2 mL of pyridine at room temperature. After 3 h the reaction mixture was diluted with water and extracted with ethyl acetate (3×10 mL). The combined organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by medium pressure liquid chromatography using 20-100% ethyl acetate in hexanes as eluent to give 25 mg of the title product, a compound of the present invention, as a white solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by medium pressure liquid chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6257b6a8384e4af4add65e7ab754ab21
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288375B2

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