Methanesulfonic Acid → HCID 86647658, compound

HRID 1798702Notes

Reaction equation

HRID 1798702 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1[C:7]([CH2:15][O:16][C:17]2[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]=2)=[CH:8][N:9]2[C:14]=1[CH:13]=[CH:12][CH:11]=[N:10]2>C(Cl)Cl.C(OCC)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1[C:7]([CH2:15][O:16][C:17]2[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]=2)=[CH:8][N:9]2[C:14]=1[CH:13]=[CH:12][CH:11]=[N:10]2

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 49779046HCID 49779046, compound

Product 1

HCID 86647658HCID 86647658, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (34.8 mg, 0.36 mmol) was added to a solution of compound 4-(4-(imidazo[1,2-b]pyridazin-2-ylmethoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (160 mg, 0.36 mmol) in DCM (3 ml) and diethyl ether (15 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. The solids were dried under vacuo to afford 4-(4-(imidazo[1,2-b]pyridazin-2-ylmethoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonate (110 mg, 56%) as a white solid. 1H NMR: 500 MHz, DMSO-d6: δ 8.45 (s, 1H), 8.4 (s, 1H) 8.15 (d, 1H), 7.55 (d, 2H), 7.25 (d, 1H), 7.15 (d, 2H), 7.1 (d, 2H), 7.0 (d, 2H), 5.25 (s, 2H), 3.8 (s, 3H), 2.35 (s, 3H), 1.25 (s, 6H), HPLC: (98.5%, Condition-A).

Workup

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

Sources & evidence

ORD record
ord-2210d4b14d644b69ab3fc91f3792dbdb
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

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