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Triethylamine → 1-{4-[(2-Aminoimidazo[1,2-b]pyridazin-6-yl)ethynyl]phenyl}-3-(3-methylphenyl)urea

HRID 589896
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 589896
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH2:11])[N:10]=2)[N:7]=1.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=2)=[O:22])=[CH:16][CH:15]=1)#[CH:13].C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[NH2:11][C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([C:13]#[C:12][C:14]3[CH:15]=[CH:16][C:17]([NH:20][C:21]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=4)=[O:22])=[CH:18][CH:19]=3)=[N:7][N:6]2[CH:8]=1
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Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 574410246-Iodoimidazo[1,2-B]pyridazin-2-amineHCID 1186384341-(4-Ethynylphenyl)-3-(3-methylphenyl)urea

Produkt 1

HCID 1186384141-{4-[(2-Aminoimidazo[1,2-b]pyridazin-6-yl)ethynyl]phenyl}-3-(3-methylphenyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a nitrogen bubbled solution of 6-iodo-imidazo[1,2-b]pyridazin-2-ylamine (260 mg, 1 mmol, 1 eq) and 1-(4-ethynylphenyl)-3-(3-methylphenyl)urea (375 mg, 1.5 eq) in DMF (5 mL) was added triethylamine (0.56 mL, 4 eq), bis(triphenylphosphine)palladium(II) dichloride (70.2 mg, 0.1 eq), and copper(I) iodide (38.1 mg, 0.2 eq). The reaction mixture was stirred at room temperature for 10 minutes and then partitioned between saturated aq NaHCO3 and i-PrOH—CHCl3 (1:4). The aqueous layer was extracted once more with i-PrOH—CHCl3 (1:4). The two organic layers were combined, washed with brine, and dried with anhydrous Na2SO4. The upper clear liquid was decanted, concentrated with silica gel, and the solid mixture was chromatographed (eluted from DCM to MeOH-DCM 1:15). The product fractions were collected and concentrated. The solid residue was triturated with EtOAc-Hex (1:1) and gave 1-{4-[(2-aminoimidazo[1,2-b]pyridazin-6-yl)ethynyl]phenyl}-3-(3-methylphenyl)urea as a brown solid upon filtration in amount of 133 mg.

Aufarbeitung

  1. custompartitioned between saturated aq NaHCO3 and i-PrOH—CHCl3 (1:4)
  2. extractionThe aqueous layer was extracted once more with i-PrOH—CHCl3 (1:4)
  3. washwashed with brine
  4. dry with materialdried with anhydrous Na2SO4
  5. customThe upper clear liquid was decanted
  6. concentrationconcentrated with silica gel
  7. customthe solid mixture was chromatographed
  8. wash(eluted from DCM to MeOH-DCM 1:15)
  9. customThe product fractions were collected
  10. concentrationconcentrated
  11. customThe solid residue was triturated with EtOAc-Hex (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-23b537517f624047ab6905b106169cff
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09233968B1

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