Acetic Acid → HCID 70999680, compound

HRID 1878564Notes

Reaction equation

HRID 1878564 reaction equation
[N:1]1([C:7]2[N:12]3[N:13]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:15]=[C:11]3[N:10]=[C:9]([NH:22][NH2:23])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:24][C:25]1([CH3:34])[CH2:29][C:28]2[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=2[O:26]1.[C:35](O)(=O)C.O>C(O)C>[CH3:24][C:25]1([CH3:34])[CH2:29][C:28]2[CH:30]=[CH:31][CH:32]=[C:33]([CH:35]=[N:23][NH:22][C:9]3[CH:8]=[C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[N:12]4[N:13]=[C:14]([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)[CH:15]=[C:11]4[N:10]=3)[C:27]=2[O:26]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 806402,3-Dihydro-2,2-dimethylbenzofuranHCID 70867226HCID 70867226, compound

Product 1

HCID 70999680HCID 70999680, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-morpholin-4-yl-2-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl-hydrazine (20 mg, 0.065 mM) in absolute ethanol (2.0 mL), there were added 2,2-dimethyl-2,3-dihydro-benzofuran (17 mg, 0.097 mM) and acetic acid (2.0 μL) and the mixture was stirred at room temperature for 3 hours. Water was added to the mixture, the mixture was then extracted with ethyl acetate and then the resulting organic phase was washed with a saturated aqueous common salt solution. After the drying of the organic phase over anhydrous magnesium sulfate, the organic phase was concentrated under reduced pressure. The resulting residue was purified by the NH-silica gel column chromatography (ethyl acetate:hexane=1:2) to thus give the title compound (18 mg, yield: 60%).

Workup

  1. extractionthe mixture was then extracted with ethyl acetate
  2. washthe resulting organic phase was washed with a saturated aqueous common salt solution
  3. dry with materialAfter the drying of the organic phase over anhydrous magnesium sulfate
  4. concentrationthe organic phase was concentrated under reduced pressure
  5. customThe resulting residue was purified by the NH-silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-26b9acfcefbb4d81884e3c4d3e3e762d
Source dataset
uspto-grants-2012_11
Patent number
US08314098B2

Reaction notes

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