Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 66743755, compound

HRID 2364108Notes

Reaction equation

HRID 2364108 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].[C:16]1([NH:22][CH:23]2[CH2:32][CH2:31][C:26]3(OCCO3)[CH2:25][CH2:24]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.[O-]S([O-])(=O)=O.[Mg+2].C([O-])(O)=O.[Na+]>CCOC(C)=O.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:26]3([CH2:25][CH2:24][CH:23]([NH:22][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:32][CH2:31]3)[NH:1][C:2]=2[CH:6]=1

Participants

8

Reactant 5

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 11379291HCID 11379291, compoundHCID 667430133-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide

Product 1

HCID 66743755HCID 66743755, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-amino-5-(5-methyl-1H-pyrazol-4-yl)thiophene-2-carboxamide (146 mg, 0.66 mmol), N-phenyl-1,4-dioxaspiro [4.5]decan-8-amine (169 mg, 0.723 mmol), CSA (183 mg, 0.788 mmol), MgSO4 (158 mg, 1.31 mmol) and DMA (1 mL) was stirred at 100° C. for 1 h. EtOAc and saturated aqueous NaHCO3 were added to quench the reaction. The organic materials were extracted with EtOAc/THF. The combined extracts were dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, NH, 95:5 hexane/EtOAc to EtOAc then to 95:5 EtOAc/MeOH), then crystallized from 2-propanol/heptane to give the title compound (41 mg, 16%) as a yellow solid:

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe organic materials were extracted with EtOAc/THF
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. customAfter removal of the solvent at reduced pressure
  7. customthe residue was purified by column chromatography (Purif, NH, 95:5 hexane/EtOAc to EtOAc
  8. customto 95:5 EtOAc/MeOH), then crystallized from 2-propanol/heptane

Sources & evidence

ORD record
ord-8f847d9b16af436892278421bfdbb602
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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