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Formaldehyde → 7-Fluoro-6-{6-[1-(1-methyl-azetidin-3-yl)-1H-pyrazol-4-yl]-imidazo[1,2-b]pyridazin-3-yl methyl}-quinoline

HRID 69183
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 69183
CO.[NH:3]1[CH2:6][CH:5]([N:7]2[CH:11]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]4[N:16]([C:18]([CH2:21][C:22]5[CH:23]=[C:24]6[C:29](=[CH:30][C:31]=5[F:32])[N:28]=[CH:27][CH:26]=[CH:25]6)=[CH:19][N:20]=4)[N:17]=3)[CH:9]=[N:8]2)[CH2:4]1.C=O.[BH3-][C:36]#N.[Na+]>C(Cl)Cl.C(O)(=O)C>[F:32][C:31]1[CH:30]=[C:29]2[C:24]([CH:25]=[CH:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[CH2:21][C:18]1[N:16]2[N:17]=[C:12]([C:10]3[CH:9]=[N:8][N:7]([CH:5]4[CH2:4][N:3]([CH3:36])[CH2:6]4)[CH:11]=3)[CH:13]=[CH:14][C:15]2=[N:20][CH:19]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 686314996-[6-(1-Azetidin-3-yl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-7-fluoro-quinoline

Produkt 1

HCID 579174527-Fluoro-6-{6-[1-(1-methyl-azetidin-3-yl)-1H-pyrazol-4-yl]-imidazo[1,2-b]pyridazin-3-yl methyl}-quinoline

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A flask was charged with MeOH (1 mL). 6-[6-(1-Azetidin-3-yl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-7-fluoro-quinoline (Stage 146.1, 26 mg, 0.065 mmol), formaldehyde (9.7 μL, 0.130 mmol) and NaBH3CN (20 mg, 0.325 mmol) were then added. The pH was adjusted to 5-6 with a drop of acetic acid and the RM was stirred at rt for 2 h. The mixture was then diluted with DCM, washed with NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (CombiFlash® Companion System®, with a 4 g RediSep® silica gel column, DCM/(DCM/MeOH 19:1)=100:0→0:100)). The residue crystallized in DCM. The solid was filtered off, and dissolved in EtOAc. The solution was washed again with NaHCO3, dried over Na2SO4, filtered and concentrated to afford the title compound as a foam (tR 2.93 min (conditions 3), MH+=414.1, 1H-NMR in DMSO-d6: 8.85 (m, 1H); 8.60 (s, 1H); 8.35 (m, 1H); 8.09 (m, 3H); 7.77 (m, 1H); 7.58 (m, 2H); 7.47 (m, 1H); 5.01 (m, 1H); 4.55 (s, 2H); 3.71 (m, 2H); 3.40 (m, 2H); 2.34 (s, 3H))

Aufarbeitung

  1. washwashed with NaHCO3 and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (CombiFlash® Companion System®
  6. customThe residue crystallized in DCM
  7. filtrationThe solid was filtered off
  8. dissolutiondissolved in EtOAc
  9. washThe solution was washed again with NaHCO3
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d7db261cf07346c18aa7a6a50df3ea6b
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822468B2

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