6-Chloro-3-hydrazinylpyridazin-4-amine → 6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-amine

HRID 873974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 873974
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH2:9])=[C:4]([NH2:10])[CH:3]=1.[C:11]([O-])(=O)[CH3:12].[K+]>CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]2[N:6]([C:11]([CH3:12])=[N:9][N:8]=2)[N:7]=1

Komponenten

4

Edukt 2

HCID 2500056-Chloro-3-hydrazinylpyridazin-4-amineHCID 517044Potassium Acetate

Produkt 1

HCID 717568126-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-8-amineAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A MW vial was charged with 6-chloro-3-hydrazinylpyridazin-4-amine (Step 112.2) (475 mg, 2.98 mmol) and potassium acetate (467 mg, 4.76 mmol) in AcOH (5 mL). The MW vial was sealed and the resulting mixture was heated up and stirred at 170° C. for 4 hr. The reaction was cooled down to RT and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (NH3 1%/CH2Cl2/MeOH 1-3%) to afford the title product (450 mg, 2.451 mmol, 82% yield). tR: 2.32 min (HPLC 1); tR: 0.55 min (LC-MS 2); ESI-MS: 184 [M+H]+ (LC-MS 2); ESI-MS: 182 [M−H]− (LC-MS 2); Rf=0.45 (CH2Cl2/MeOH 9:1).

Aufarbeitung

  1. customThe MW vial was sealed
  2. temperaturethe resulting mixture was heated up
  3. temperatureThe reaction was cooled down to RT
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel column chromatography (NH3 1%/CH2Cl2/MeOH 1-3%)

Quellen und Nachweise

ORD-Eintrag
ord-768931d1870a45dea662c9381940b6b9
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975417B2

Notizen zur Reaktion

Wird geladen…