(6-Methylpyridin-2-yl)thiourea → N-(6-methylpyridin-2-yl)-5,6-dihydro-4H-thiazolo[4,5-e]indazol-2-amine

HRID 2366497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366497
Br[CH:2]1[CH2:10][CH2:9][C:8]2[N:7](S(C3C=CC(C)=CC=3)(=O)=O)[N:6]=[CH:5][C:4]=2[C:3]1=O.[CH3:22][C:23]1[N:28]=[C:27]([NH:29][C:30]([NH2:32])=[S:31])[CH:26]=[CH:25][CH:24]=1>CCO.Cl>[CH3:22][C:23]1[N:28]=[C:27]([NH:29][C:30]2[S:31][C:2]3[CH2:10][CH2:9][C:8]4[NH:7][N:6]=[CH:5][C:4]=4[C:3]=3[N:32]=2)[CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 2

HCID 685983(6-Methylpyridin-2-yl)thioureaHCID 674593295-bromo-1-tosyl-6,7-dihydro-1H-indazol-4(5H)-one

Produkt 1

HCID 46836497N-(6-methylpyridin-2-yl)-5,6-dihydro-4H-thiazolo[4,5-e]indazol-2-amineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

According to Scheme 3 Step 4: A solution of 5-bromo-1-tosyl-6,7-dihydro-1H-indazol-4(5H)-one (0.90 mmol, 331 mg) and of 1-(6-methylpyridin-2-yl)thiourea (0.90 mmol, 150 mg) in EtOH (10 mL) and HCl (35%, 1 mL) was stirred at 80° C. for 5 hours. The reaction was quenched with the addition of a saturated solution of NaHCO3 at room temperature until pH=8. The aqueous phase was extracted with DCM. The organic phase was dried over Na2SO4 and concentrated. The crude residue was washed with Et2O and dried to yield N-(6-methylpyridin-2-yl)-5,6-dihydro-4H-thiazolo[4,5-e]indazol-2-amine (0.78 mmol, 220 mg, 87%) as a white solid.

Aufarbeitung

  1. customThe reaction was quenched with the addition of a saturated solution of NaHCO3 at room temperature until pH=8
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. washThe crude residue was washed with Et2O
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d25b034159644174bbb31df687b8094b
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697744B2

Notizen zur Reaktion

Wird geladen…