Sodium Carbonate → HCID 25098000, compound

HRID 1962940Notes

Reaction equation

HRID 1962940 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[N:8]=[CH:7][C:6]([C:9]#[C:10][C:11](=O)[CH3:12])=[CH:5][CH:4]=1.C([O-])(=O)C.[C:20]([NH:24][S:25]([C:28]1[CH:29]=[C:30]([C:34]2[N:39]=[C:38]([C:40]([NH2:42])=[NH2+:41])[CH:37]=[CH:36][CH:35]=2)[CH:31]=[CH:32][CH:33]=1)(=[O:27])=[O:26])([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[C:20]([NH:24][S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]2[CH:35]=[CH:36][CH:37]=[C:38]([C:40]3[N:42]=[C:11]([CH3:12])[CH:10]=[C:9]([C:6]4[CH:7]=[N:8][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:4][CH:5]=4)[N:41]=3)[N:39]=2)[CH:29]=1)(=[O:27])=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 67393385HCID 67393385, compoundHCID 67393589HCID 67393589, compound

Product 1

HCID 25098000HCID 25098000, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Condensation reaction: The above described 4-(6-trifluoromethyl-pyridin-3-yl)-but-3-yn-2-one (53 mg, 0.25 mmol), 6-(3-tert-butylsulfamoyl-phenyl)-pyridine-2-carboxamidinium acetate (Example 26, amidine part, steps 1 to 4) (118 mg, 0.3 mmol) and sodium carbonate (64 mg, 0.6 mmol) were dissolved in acetonitrile (2 ml) and treated by microwave irradiation at 120° C. for 60 min. The reaction mixture was extracted with ethyl acetate and water, the organic layers were combined, dried over MgSO4, filtered and the solvents were evaporated to give a crude product, which was purified by flash chromatography with n-heptane and ethyl acetate to give the title compound as a light brown foam (100 mg, 76%). MS (ISP) 528.2 [(M+H)+].

Workup

  1. customCondensation reaction
  2. additiontreated by microwave irradiation at 120° C. for 60 min
  3. extractionThe reaction mixture was extracted with ethyl acetate and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were evaporated
  7. customto give a crude product, which
  8. customwas purified by flash chromatography with n-heptane and ethyl acetate

Sources & evidence

ORD record
ord-921e912da890446c90d82b3d666c1bc8
Source dataset
uspto-grants-2013_04
Patent number
US08415380B2

Reaction notes

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