Sulfuric Acid → 6-[1-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-vinyl]-quinoline

反応式

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[CH:19][CH:18]=[CH:17]4)(O)[CH3:12])=[CH:9][N:10]=2)[N:7]=1.S(=O)(=O)(O)O.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[CH:19][CH:18]=[CH:17]4)=[CH2:12])=[CH:9][N:10]=2)[N:7]=1

参加物

実験手順

(rac)-1-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-1-quinolin-6-yl-ethanol (Stage 154.1, 50 mg, 0.154 mmol) was dissolved in acetic acid >99% (0.150 mL) and sulfuric acid conc. 98% (0.050 mL) and the mixture was heated to reflux for 1 h. After cooling down to rt, ice water was added. The mixture was basified with NaOH 1 N and extracted with EtOAc twice. Combined organic layers were washed with brine and dried on Na2SO4. After evaporation of the solvent the crude was purified by preparative HPLC with acetonitrile/water (with 0.1% TFA) to afford the title compound as a yellow solid (tR 1.10 min (conditions 1), (MH+=307).