methyl N-(2-chloroacetyl)carbamate → N-[7-[3-[(methylamino)carbonyl]phenyl]imidazo[1,2-b]pyridazin-2-yl]carbamic acid methyl ester

HRID 1097309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097309
[NH2:1][CH:2]1[NH:7][N:6]=[CH:5][C:4]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([NH:13][CH3:14])=[O:12])=[CH:3]1.Cl[CH2:19][C:20]([NH:22][C:23](=[O:26])[O:24][CH3:25])=O>CN(C=O)C>[CH3:25][O:24][C:23](=[O:26])[NH:22][C:20]1[N:1]=[C:2]2[CH:3]=[C:4]([C:8]3[CH:17]=[CH:16][CH:15]=[C:10]([C:11](=[O:12])[NH:13][CH3:14])[CH:9]=3)[CH:5]=[N:6][N:7]2[CH:19]=1

Komponenten

4

Edukt 2

HCID 518783methyl N-(2-chloroacetyl)carbamateHCID 594434953-(6-Amino-1,6-dihydro-pyridazin-4-yl)-N-methyl-benzamide

Produkt 1

HCID 59443506N-[7-[3-[(methylamino)carbonyl]phenyl]imidazo[1,2-b]pyridazin-2-yl]carbamic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

3-(6-Amino-1,6-dihydro-pyridazin-4-yl)-N-methyl-benzamide (Intermediate A—Step E) (1 eq, 2.74 mmol, 735 mg) is added to a solution of methyl (chloroacetyl)carbamate (1.2 eq, 3.28 mmol, 498 mg) in DMF (30 ml) and the reaction mixture is stirred at 110° C. for 7.5 h. The solvent is then removed in vacuo and the product is purified by flash column chromatography eluting with 9:1 DCM/MeOH to afford [7-(3-Methylcarbamoyl-phenyl)-imidazo-[1,2-b]-pyridazin -2-yl]-carbamic acid methyl ester as a green solid; [M+H]+=326

Aufarbeitung

  1. customThe solvent is then removed in vacuo
  2. customthe product is purified by flash column chromatography
  3. washeluting with 9:1 DCM/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-1ed9606eb601431ca3f0f2cdd94a0461
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143253B2

Notizen zur Reaktion

Wird geladen…