Methanesulfonic Acid → HCID 86647663, compound

HRID 1798713Notes

Reaction equation

HRID 1798713 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][C:7]1([CH3:36])[O:11][C:10]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][N:29]=3)=[CH:22][CH:21]=2)[C:8]1=[O:35]>C(Cl)Cl.C(OCC)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][C:7]1([CH3:36])[O:11][C:10]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][N:29]=3)=[CH:22][CH:21]=2)[C:8]1=[O:35]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 66644052HCID 66644052, compound

Product 1

HCID 86647663HCID 86647663, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (36 mg, 0.3 mmol) was added to a solution of 4-(5,5-dimethyl-3-(4-((5-methylpyridin-2-yl)methoxy)phenyl)-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile (150 mg, 0.3 mmol) in DCM (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 4-(5,5-dimethyl-3-(4-((5-methylpyridin-2-yl)methoxy)phenyl)-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile methanesulfonate (120 mg, 67.0%) as a white solid. 1H NMR: 200 MHz, DMSO-d6: δ 8.5 (s, 1H), 7.6 (d, 1H), 7.55 (d, 2H), 7.4 (d, 1H), 7.2 (d, 2H), 7.1 (d, 2H), 7.0 (d, 2H), 5.2 (s, 2H), 2.35 (s, 3H), 2.3 (s, 3H), 1.45 (s, 6H). HPLC: (98.3%, 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-c29c342393304d04bbb5e4e73c487406
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

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