Sodium Bicarbonate → HCID 58056831, compound

HRID 1256594Notes

Reaction equation

HRID 1256594 reaction equation
[F:1][C:2]1([F:16])[C:10]2[C:5](=[CH:6][C:7]([NH:12][CH3:13])=[C:8]([NH2:11])[CH:9]=2)[C:4]([F:15])([F:14])[O:3]1.O[CH:18]([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)S([O-])(=O)=O.[Na+].C(=O)([O-])O.[Na+]>CN(C=O)C>[F:16][C:2]1([F:1])[C:10]2=[CH:9][C:8]3[N:11]=[C:18]([C:23]4[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=4)[N:12]([CH3:13])[C:7]=3[CH:6]=[C:5]2[C:4]([F:14])([F:15])[O:3]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23695668HCID 23695668, compoundHCID 58056765HCID 58056765, compound

Product 1

HCID 58056831HCID 58056831, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 0.59 g of 1,1,3,3-tetrafluoro-N-methyl-1,3-dihydroisobenzofuran-5,6-diamine, 0.63 g of sodium hydroxy-pyridin-4-yl-methanesulfonate and 5 ml of DMF was stirred for 1 hour while heating at 120° C. After cooling down to room temperature, a saturated sodium hydrogen carbonate aqueous solution was poured, and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.71 g of 5,5,7,7-tetrafluoro-1-methyl-2-(pyridin-4-yl)-5,7-dihydro-1H-furo[3′,4′:4,5]benzo[1,2-d]imidazole (hereinafter, referred to as present active compound 1).

Workup

  1. temperatureAfter cooling down to room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-464630972fde4d3b9e60bfdbde153829
Source dataset
uspto-grants-2013_06
Patent number
US08461181B2

Reaction notes

Loading…