Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 25069654, compound

HRID 876688Notes

Reaction equation

HRID 876688 reaction equation
CO[C:3](=[O:18])[C:4]([C:9]1[S:10][C:11]([C:14]([F:17])([F:16])[F:15])=[N:12][N:13]=1)=[CH:5][N:6](C)C.[NH:19]([C:21]1[CH:26]=[C:25]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[N:24]=[CH:23][N:22]=1)N.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.CC[O-].[Na+].C[O-].[Na+]>C(O)C.CO>[N:27]1([C:25]2[N:24]=[CH:23][N:22]=[C:21]([N:19]3[C:3](=[O:18])[C:4]([C:9]4[S:10][C:11]([C:14]([F:15])([F:16])[F:17])=[N:12][N:13]=4)=[CH:5][NH:6]3)[CH:26]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

8

Reactant 5

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 2723922Sodium ethoxideHCID 10942334Sodium MethoxideHCID 441403054-Hydrazinyl-6-(piperidin-1-yl)pyrimidineHCID 674565093-(Dimethylamino)-2-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]acrylic acid methyl ester

Product 1

HCID 25069654HCID 25069654, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

240 mg (854 μmol) of the compound from Example 2A, 150 mg (776 mmol) of the compound from Example 8A and 18 mg (78 mmol) camphor-10-sulfonic acid are dissolved in 3 ml anhydrous ethanol and the mixture is heated under reflux overnight. After cooling, 64 mg (931 mmol) sodium ethylate are added and the mixture is further stirred overnight at RT. The precipitate formed is filtered off with suction, washed with ethanol and diethyl ether and dried. The filtrate is concentrated and the residue is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient). The two intermediate product fractions obtained in this way are suspended together in 5 ml methanol, 15 mg (278 μmol) sodium methylate are added and the mixture is heated under reflux overnight. After cooling, the reaction mixture is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient) and 26 mg (8% of th.) of the title compound are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. customThe precipitate formed
  5. filtrationis filtered off with suction
  6. washwashed with ethanol and diethyl ether
  7. customdried
  8. concentrationThe filtrate is concentrated
  9. customthe residue is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)
  10. customThe two intermediate product fractions obtained in this way
  11. temperaturethe mixture is heated
  12. temperatureunder reflux overnight
  13. temperatureAfter cooling
  14. customthe reaction mixture is purified by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient) and 26 mg (8% of th.) of the title compound
  15. customare obtained

Sources & evidence

ORD record
ord-767e5735fb52400892e9234aa418626e
Source dataset
uspto-grants-2015_03
Patent number
US08987261B2

Reaction notes

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