Methanesulfonic Acid → 4-(4-(imidazo[1,2-b]pyridazin-6-ylmethoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonate

HRID 1798698Notes

Reaction equation

HRID 1798698 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1[CH:7]=[CH:8][N:9]2[C:14]=1[CH:13]=[CH:12][C:11]([CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]3[C:24](=[O:38])[C:25]([CH3:37])([CH3:36])[O:26][C:27]=3[C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)=[CH:19][CH:18]=1)=[N:10]2>C(Cl)Cl.C(OCC)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1[CH:7]=[CH:8][N:9]2[C:14]=1[CH:13]=[CH:12][C:11]([CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]3[C:24](=[O:38])[C:25]([CH3:36])([CH3:37])[O:26][C:27]=3[C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)=[CH:21][CH:22]=1)=[N:10]2

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 497789784-(4-(imidazo[1,2-b]pyridazin-6-ylmethoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one

Product 1

HCID 866476574-(4-(imidazo[1,2-b]pyridazin-6-ylmethoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonateYield 89.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (54 mg, 0.5 mmol) was added to a solution of compound 4-(4-(imidazo[1,2-b]pyridazin-6-ylmethoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (250 mg, 0.5 mmol) in DCM (2 ml) and diethyl ether (20 mL) at RT under an atmosphere of nitrogen. The reaction mixture was stirred at RT for 4 h upon which the mixture was filtered and the solids were washed with 20% DCM in diethyl ether and dried in vacuo to afford 4-(4-(imidazo[1,2-b]pyridazin-6-ylmethoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonate (240 mg, 80.0%) as an off-white solid. 1H NMR: 200 MHz, DMSO-d6: δ 8.55 (s, 1H), 8.35 (d, 1H), 78.1 (s, 1H), 7.65 (d, 2H), 7.4 (d, 1H), 7.2 (d, 2H), 7.1 (d, 2H), 7.0 (d, 2H), 5.35 (s, 2H), 3.9 (s, 3H), 2.35 (s, 3H), 1.45 (s, 6H). HPLC: (98.3%, Condition-A).

Workup

  1. filtrationwas filtered
  2. washthe solids were washed with 20% DCM in diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-2de46783154f4e4b875a29c2f64b8446
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

Loading…