Hydrogen Bromide → HCID 178420878, compound

HRID 2248807Notes

Reaction equation

HRID 2248807 reaction equation
FC1C=CC(C[N:9]2[C:17]([S:18][CH:19]3[CH2:24][CH2:23][N:22](S(C4C=CC(C)=CC=4)(=O)=O)[CH2:21][CH2:20]3)=[N:16][C:15]3[C:10]2=[N:11][CH:12]=[N:13][CH:14]=3)=CC=1.Br>C(O)(=O)C>[NH:22]1[CH2:23][CH2:24][CH:19]([S:18][C:17]2[NH:9][C:10]3[C:15]([N:16]=2)=[CH:14][N:13]=[CH:12][N:11]=3)[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 19785281HCID 19785281, compound

Product 1

HCID 178420878HCID 178420878, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 24.8 parts of 4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]thio]-1-[(4-methylphenyl)sulfonyl]piperidine and 300 parts of acetic acid, saturated with hydrogen bromide was stirred overnight at room temperature. After evaporation, the residue was taken up in water. The whole was treated with a sodium hydroxide solution and extracted with dichloromethane. The extract was acidified with a hydrochloric acid solution and extracted with water. The aqueous layer was treated with a sodium hydroxide solution and the product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, (95:5 by volume)→trichloromethane and methanol, saturated with ammonia, (90:10 by volume) as eluents. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 3.0 parts (17.4%) of 9-[(4-fluorophenyl)methyl[-8-(4-piperidinylthio)-9H-purine; mp. 113.5° C. (compound 31).

Workup

  1. customAfter evaporation
  2. additionThe whole was treated with a sodium hydroxide solution
  3. extractionextracted with dichloromethane
  4. extractionextracted with water
  5. additionThe aqueous layer was treated with a sodium hydroxide solution
  6. extractionthe product was extracted with dichloromethane
  7. washThe extract was washed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography over silica gel using
  12. additiona mixture of trichloromethane and methanol, (95:5 by volume)→trichloromethane and methanol
  13. customThe pure fractions were collected
  14. customthe eluent was evaporated
  15. customThe residue was crystallized from acetonitrile
  16. filtrationThe product was filtered off
  17. customdried

Sources & evidence

ORD record
ord-8b04de644a9245adb47d790c1ed872cd
Source dataset
uspto-grants-1991_08
Patent number
US05041448

Reaction notes

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