Pyridine → HCID 9801397, compound

HRID 2307847Notes

Reaction equation

HRID 2307847 reaction equation
NOS(O)(=O)=O.C[N:8](C)[C:9](=[N:11][C:12]([C:14]1[CH:15]=[N:16][C:17]([N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[CH2:22][CH2:21]2)=[CH:18][CH:19]=1)=[S:13])[CH3:10].N1C=CC=CC=1>CO.C(O)C>[CH3:10][C:9]1[N:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=4)[CH2:22][CH2:21]3)=[N:16][CH:15]=2)[S:13][N:8]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 76284hydroxylamine-O-sulfonic acidHCID 12146677HCID 12146677, compound

Product 1

HCID 9801397HCID 9801397, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of hydroxylamine-O-sulfonic acid (0.011 mol) in methanol (15 ml) was added at once to a mixture of intermediate 5 (0.01 mol) and pyridine (0.02 mol) in ethanol (40 ml). The mixture was stirred at room temperature for 90 minutes. The solvent was evaporated. The residue was dissolved in DCM, washed with water and an aqueous NaOH 0.1N solution, dried, filtered and the solvent was evaporated. The residue was taken up in methanol, filtered off and dried. The residue was taken up in acetonitrile (100 ml). The mixture was stirred and boiled until complete dissolution and then allowed to crystallize out. The precipitate was filtered off and dried, yielding 1.4 g (35%) of 1-[5-(3-methyl-1,2,4-thiadiazol-5-yl)-2-pyridinyl]-4-[3-(trifluoromethyl)-phenyl]piperazine (compound 8).

Workup

  1. additionwas added at
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with water
  5. dry with materialan aqueous NaOH 0.1N solution, dried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. filtrationfiltered off
  9. customdried
  10. stirringThe mixture was stirred
  11. dissolutionboiled until complete dissolution
  12. customto crystallize out
  13. filtrationThe precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-6496cbdeb7114be4b8dab9009863131a
Source dataset
uspto-grants-2004_12
Patent number
US06833369B2

Reaction notes

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