N-bromobutanimide → HCID 57917273, Verbindung

HRID 69293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 69293
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH2:10][C:11]3[N:15]4[N:16]=[C:17]([C:20]5[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=5)[CH:18]=[CH:19][C:14]4=[N:13][CH:12]=3)[CH:7]=[CH:6][C:5]=12.C1C(=O)N([Br:33])C(=O)C1>C(Cl)Cl>[Br:33][C:3]1[N:4]2[CH:9]=[C:8]([CH2:10][C:11]3[N:15]4[N:16]=[C:17]([C:20]5[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=5)[CH:18]=[CH:19][C:14]4=[N:13][CH:12]=3)[CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 442062913-Imidazo[1,2-a]pyridin-6-ylmethyl-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

Produkt 1

HCID 57917273HCID 57917273, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Imidazo[1,2-a]pyridin-6-ylmethyl-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine (Example 10, 10 mg, 0.030 mmol) was dissolved in DCM (0.3 mL) with NBS (5.9 mg, 0.033 mmol). The RM was stirred at rt for 2 h. The solvent was removed. The residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA). The fractions were joined and the acetonitrile was removed. The aqueous solution was basified with 5% NaHCO3 solution and it was extracted with EtOAc/MeOH (9:1) twice. Combined organic layers was washed with brine and dried over Na2SO4, filtered and concentrated. The solid obtained was triturated with Et2O. The precipitate was filtered off to afford the title compound as a white solid (tR 0.7 min (conditions 2), MH+=408).

Aufarbeitung

  1. customThe solvent was removed
  2. customThe residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA)
  3. customthe acetonitrile was removed
  4. extractionwas extracted with EtOAc/MeOH (9:1) twice
  5. washCombined organic layers was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe solid obtained
  10. customwas triturated with Et2O
  11. filtrationThe precipitate was filtered off

Quellen und Nachweise

ORD-Eintrag
ord-4d15d5f155504882ab957d587dcffb01
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822468B2

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