Methanesulfonic Acid → HCID 86647664, compound

HRID 1842433Notes

Reaction equation

HRID 1842433 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][C:17]([CH3:20])([CH3:19])[C:16](=[O:21])[C:15]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[N:31]=[C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[N:33]4[CH:39]=3)=[CH:24][CH:23]=2)=[CH:10][CH:9]=1>C(Cl)Cl.C(OCC)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[O:18][C:17]([CH3:20])([CH3:19])[C:16](=[O:21])[C:15]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[N:31]=[C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[N:33]4[CH:39]=3)=[CH:24][CH:23]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 49779454HCID 49779454, compound

Product 1

HCID 86647664HCID 86647664, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (53.1 mg, 0.5 mmol) was added to a solution of 5-(4-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-f4fb97d375184173835fd8c272d79b83
Source dataset
uspto-grants-2015_02
Patent number
US08946222B2

Reaction notes

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