1,2-Dichloroethane → HCID 67451027, Verbindung

HRID 869184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869184
C(C[C:4]1[S:8][C:7]([C:9]2[N:14]=[N:13][C:12]([N:15]([CH2:23][C:24]3([C:28]4[C:33]([F:34])=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:27][CH2:26][CH2:25]3)C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)=[N:6][CH:5]=1)#N.Cl.CN.C1C=CC2N(O)N=[N:44][C:42]=2C=1.C(Cl)CCl.[C:52]([O:55]CC)(=O)[CH3:53]>Cl.CN(C=O)C>[F:34][C:33]1[C:28]([C:24]2([CH2:23][NH:15][C:12]3[N:13]=[N:14][C:9]([C:7]4[S:8][C:4]([CH2:53][C:52]([NH:44][CH3:42])=[O:55])=[CH:5][N:6]=4)=[CH:10][CH:11]=3)[CH2:25][CH2:26][CH2:27]2)=[N:29][CH:30]=[CH:31][CH:32]=1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 68231864HCID 68231864, Verbindung

Produkt 1

HCID 67451027HCID 67451027, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of t-butyl 6-(5-(cyanomethyl)thiazol-2-yl)pyridazin-3-yl((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)carbamate (1 g, 2 mmol) in HCl (30 mL, conc) was heated to 105° C. in a microwave reactor and stirred for 15 min. The reaction was concentrated to give 900 mg (2.3 mmol) of a crude reddish solid. To this solid was added methylamine hydrochloride (183 mg, 2.7 mmol), HOBt (365 mg, 2.7 mmol), EDC (516 mg, 2.7 mmol), DMF (30 mL), and TEA (1.3 mL, 9 mmol). The reaction was stirred at rt overnight. The reaction was then poured into ethyl acetate (200 mL), washed with water (3×100 mL), and the organic layer was separated, dried over Na2SO4, filtered, concentrated, and recrystallized from EtOAc to give 408 mg of 2-(2-(6-((1-(3-Fluoropyridin-2-yl)cyclobutyl)methylamino)pyridazin-3-yl)thiazol-5-yl)-N-methylacetamide as a white solid (M+H=413.3).

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. customto give 900 mg (2.3 mmol) of a crude reddish solid
  3. stirringThe reaction was stirred at rt overnight
  4. washwashed with water (3×100 mL)
  5. customthe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customrecrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-b7690d34ee8a46aa8723bfc402a457ae
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969346B2

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