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

HRID 69196Notes

Reaction equation

HRID 69196 reaction equation
[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

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 87523391(Rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-quinolin-6-yl-ethanol

Product 1

HCID 579174536-[1-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-vinyl]-quinoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(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).

Workup

  1. temperatureto reflux for 1 h
  2. extractionextracted with EtOAc twice
  3. washCombined organic layers were washed with brine
  4. customdried on Na2SO4
  5. customAfter evaporation of the solvent the crude
  6. customwas purified by preparative HPLC with acetonitrile/water (with 0.1% TFA)

Sources & evidence

ORD record
ord-f623bcd22abb4f858215235b2e9e0bff
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

Loading…