Methanesulfonic Acid → HCID 86647664, compound

HRID 1798718Notes

Reaction equation

HRID 1798718 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][C:7]1([CH3:31])[C:11](=[O:12])[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[N:22]=[C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]4[CH:30]=3)=[CH:15][CH:14]=2)=[CH:9][O:8]1>C(Cl)Cl.C(OCC)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:9]2[O:8][C:7]([CH3:31])([CH3:6])[C:11](=[O:12])[C:10]=2[C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]3[N:22]=[C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]4[CH:30]=3)=[CH:17][CH:18]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 86647665HCID 86647665, compound

Product 1

HCID 86647664HCID 86647664, compoundYield 174.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (53.1 mg, 0.5 mmol) was added to a solution of 544-methoxyphenyl)-2,2-dimethyl-4-(4-((5-methylimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)furan-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, dried in vacuo to afford 5-(4-methoxyphenyl)-2,2-dimethyl-4-(4-((5-methylimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)furan-3(2H)-one methanesulfonate (240 mg, 82.7%) as white solid: 1H NMR: 500 MHz, DMSO-d6: δ 7.95 (s, 1H), 7.6 (d, 2H), 7.4 (d, 1H), 7.25 (t, 1H), 7.2 (d, 3H), 7.15 (d, 2H), 7.0 (d, 2H), 6.8 (d, 1H), 5.2 (s, 2H), 3.85 (s, 3H), 2.6 (s, 3H), 2.5 (s, 3H), 1.25 (s, 6H), HPLC: (98.4%, Condition-A).

Workup

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

Sources & evidence

ORD record
ord-07281e08218b49929b713fccbafd66ed
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

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