Methanesulfonic Acid → 4-(4-((6-chloroimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonate

HRID 1798721Notes

Reaction equation

HRID 1798721 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[C:14]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[C:25](=[O:39])[C:26]([CH3:38])([CH3:37])[O:27][C:28]=4[C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=4)=[CH:20][CH:19]=3)[N:15]=2)[CH:12]=1>C(Cl)Cl.C(OCC)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[C:14]([CH2:16][O:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]4[C:25](=[O:39])[C:26]([CH3:37])([CH3:38])[O:27][C:28]=4[C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=4)=[CH:22][CH:23]=3)[N:15]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 497796644-(4-((6-chloroimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)-5-(4-methoxy phenyl)-2,2-dimethylfuran-3(2H)-one

Product 1

HCID 866476664-(4-((6-chloroimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonateYield 84.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (53.1 mg, 0.5 mmol) was added to a solution of compound 4-(4-((6-chloroimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (250 g, 0.5 mmol) in DCM (2.5 ml) and diethyl ether (50 mL) at RT under an atmosphere of nitrogen. The reaction mixture was stirred at RT for 4 h upon which the solids were collected by filtration, washed with 20% DCM in diethyl ether and dried in vacuo to afford 4-(4-((6-chloroimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonate (240 mg, 82%) as a white solid. 1H NMR: 500 MHz, DMSO-d6: δ 8.8 (s, 1H), 8.3 (s, 1H), 8.0 (s, 1H), 7.6 (d, 2H), 7.4 (d, 1H), 7.15 (d, 2H), 7.1 (d, 2H), 7.0 (d, 2H) 5.35 (s, 2H), 3.8 (s, 3H), 2.3 (s, 3H), 1.4 (s, 6H), HPLC: (99.3%, Condition-A).

Workup

  1. filtrationwere collected by filtration
  2. washwashed with 20% DCM in diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e77ef035209f4d54b7362a014c0124bc
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

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