2-Indanone → HCID 66743997, compound

HRID 2364096Notes

Reaction equation

HRID 2364096 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[N:9][NH:10][C:11]=2[CH3:12])[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[CH2:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][C:17]1=O.[O-]S([O-])(=O)=O.[Mg+2].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C([O-])(O)=O.[Na+]>CCOC(C)=O.C1COCC1.CC(N(C)C)=O>[CH3:12][C:11]1[NH:10][N:9]=[CH:8][C:7]=1[C:5]1[S:4][C:3]2[C:13](=[O:14])[NH:15][C:17]3([CH2:16][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18]3)[NH:1][C:2]=2[CH:6]=1

Participants

8

Reactant 5

HCID 119832-IndanoneHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 667430133-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide

Product 1

HCID 66743997HCID 66743997, compoundYield 12.5%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene -2-carboxamide (111 mg, 0.50 mmol), 2-indanone (330 mg, 2.50 mmol), MgSO4 (120 mg, 1.00 mmol), CSA (11.6 mg, 0.050 mmol) and DMA (3 mL) was stirred at 80° C. for 1 h. The mixture was poured into saturated aqueous NaHCO3 and 2:1 EtOAc/THF. The organic layer was collected, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, hexane to EtOAc, then to 90:10 EtOAc/MeOH), then triturated with EtOAc, and the precipitate was collected by filtration to afford the title compound (21 mg, 12%) as a beige solid:

Workup

  1. customThe organic layer was collected
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (Purif, silica gel, hexane to EtOAc
  6. customto 90:10 EtOAc/MeOH), then triturated with EtOAc
  7. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-efcfcc97929b4f63be0e947ab51dd6f2
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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