Sodium Bicarbonate → HCID 59516937, compound

HRID 1698611Notes

Reaction equation

HRID 1698611 reaction equation
F[B-](F)(F)F.[CH3:6][O+](C)C.[F:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=1[CH:21]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[N:36]=[C:35]([CH3:37])[O:34][N:33]=2)=[CH:28][CH:27]=1)[C:22]([NH2:24])=[S:23].C(=O)([O-])O.[Na+]>ClCCl>[CH3:6][S:23][C:22](=[NH:24])[CH:21]([C:12]1[CH:13]=[C:14]([O:19][CH3:20])[C:15]([O:17][CH3:18])=[CH:16][C:11]=1[F:10])[NH:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[N:36]=[C:35]([CH3:37])[O:34][N:33]=2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 59517007HCID 59517007, compound

Product 1

HCID 59516937HCID 59516937, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

After adding 3.62 g of trimethyloxonium tetrafluoroborate (hereinafter, “Me3O+BR4−”) to a solution of 8.59 g of 2-(2-fluoro-4,5-dimethoxyphenyl)-2-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]thioacetamide in 400 ml of dichloromethane under a nitrogen atmosphere, the mixture was stirred at room temperature for 15 hours. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture and extraction was performed with dichloromethane. After washing the organic layer with saturated brine, it was dried over anhydrous sodium sulfate. The desiccating agent was filtered, and the filtrate was concentrated under reduced pressure to give the title compound (8.89 g, crude product) as an oil.

Workup

  1. washAfter washing the organic layer with saturated brine, it
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. filtrationThe desiccating agent was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9267fed7f4fc4d16880268a171939428
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

Loading…