Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 25074375, compound

HRID 242268Notes

Reaction equation

HRID 242268 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[N:26]=[CH:25][N:24]=[C:23]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH:22]=1)N.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CO>[N:27]1([C:23]2[N:24]=[CH:25][N:26]=[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:22]=2)[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 13393622(6-Morpholin-4-ylpyrimidin-4-yl)hydrazineHCID 674565093-(Dimethylamino)-2-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]acrylic acid methyl ester

Product 1

HCID 25074375HCID 25074375, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.43 g (8.62 mmol) of the compound from Example 2A, 1.53 g of the compound from Example 16A and 182 mg (784 μmol) camphor-10-sulfonic acid are dissolved in 35 ml anhydrous methanol and the mixture is heated under reflux overnight. After cooling, the mixture is concentrated, the residue is taken up again in 325 ml methanol, 0.5 ml (8.62 mmol) of a 25% strength methanolic sodium methylate solution is added and the mixture is heated again under reflux overnight. After cooling, the precipitate formed is filtered off with suction, washed with diethyl ether and suspended in a little water, an excess of 1 M hydrochloric acid is added and the suspension is concentrated again. The residue is washed with water and diethyl ether and dried. 1.34 g (43% of th.) of the title compound are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. concentrationthe mixture is concentrated
  5. addition0.5 ml (8.62 mmol) of a 25% strength methanolic sodium methylate solution is added
  6. temperaturethe mixture is heated again
  7. temperatureunder reflux overnight
  8. temperatureAfter cooling
  9. customthe precipitate formed
  10. filtrationis filtered off with suction
  11. washwashed with diethyl ether
  12. additionan excess of 1 M hydrochloric acid is added
  13. concentrationthe suspension is concentrated again
  14. washThe residue is washed with water and diethyl ether
  15. customdried

Sources & evidence

ORD record
ord-bfcc0c9cffb745b4a338f86bf5ef153a
Source dataset
uspto-grants-2014_02
Patent number
US08653111B2

Reaction notes

Loading…