Triethylamine → N-cyclopropyl-3-[2-(2,4-difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl]-4-methoxybenzamide

HRID 1454960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1454960
[F:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[CH:12][C:13](=[O:26])[C:14]=2[C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[C:18]([OH:20])=O)[N:10]=1.C(N(CC)CC)C.C(OC(Cl)=O)C.[CH:45]1([NH2:48])[CH2:47][CH2:46]1>C(Cl)Cl>[CH:45]1([NH:48][C:18](=[O:20])[C:17]2[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:15]([C:14]3[C:13](=[O:26])[CH:12]=[CH:11][N:9]4[C:8]=3[CH:7]=[CH:6][C:5]([O:4][C:3]3[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:2]=3[F:1])=[N:10]4)[CH:16]=2)[CH2:47][CH2:46]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 69828CyclopropylamineHCID 575312343-(2-(2,4-Difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl)-4-methoxybenzoic acid

Produkt 1

HCID 16749900N-cyclopropyl-3-[2-(2,4-difluorophenoxy)-6-oxo-6H-pyrido[1,2-b]pyridazin-5-yl]-4-methoxybenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of Intermediate 1 in CH2Cl2 was added triethyl amine and ethylchloroformate at 0° C. The mixture was warmed to ambient temperature and stirred for 10 min. The reaction was complete by LCMS analysis and concentrated in vacuo to yield crude residue. To the crude residue was added CH2Cl2 and cyclopropyl amine, followed by stirring for ½ hr. LCMS indicated the reaction was complete. The reaction was diluted with CH2Cl2, washed with 0.5 N NaOH, H2O, brine, dried over MgSO4, and concentrated in vacuo. The crude residue was purified via silica gel chromatography (EtOAc/CH2Cl2/MeOH).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customto yield crude residue
  3. stirringby stirring for ½ hr
  4. washwashed with 0.5 N NaOH, H2O, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified via silica gel chromatography (EtOAc/CH2Cl2/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-1a7c0f80ffb245ffa7ee7dbc5d71ecd7
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482345B2

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