Ethanol → HCID 178513112, compound

HRID 1021328Notes

Reaction equation

HRID 1021328 reaction equation
[C:1]([NH:4][C:5](=[O:32])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:21]=[N:22][C:23]([O:26]C(C)(C)C)=[CH:24][CH:25]=3)[CH2:16][CH2:15]2)[C:9]=1[F:31])(=[NH:3])[NH2:2].C(O)(C(F)(F)F)=O.CCO.[C:43]([OH:52])(=[O:51])[C@@H:44]([C@H:46]([C:48]([OH:50])=[O:49])[OH:47])[OH:45]>ClCCl>[C:48]([C@@H:46]([C@H:44]([C:43]([OH:52])=[O:51])[OH:45])[OH:47])([OH:50])=[O:49].[C:1]([NH:4][C:5](=[O:32])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23](=[O:26])[NH:22][CH:21]=3)[CH2:16][CH2:15]2)[C:9]=1[F:31])(=[NH:2])[NH2:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 6422Trifluoroacetic acidHCID 444305L-Tartaric acidHCID 178450190HCID 178450190, compound

Product 1

HCID 178513112HCID 178513112, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[4-(6 tert-Butoxypyridin-3-yl)piperazin-1-yl]-2-fluorobenzyl carbamimidoylcarbamate (132 mg) was dissolved in dichloromethane (3.4 ml), and TFA (508 mg) was added thereto, followed by stirring at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, the residue was mixed with CHCl3/MeOH, and basic silica gel was added thereto, followed by concentrating under reduced pressure. The residue was purified by basic silica gel column chromatography (CHCl3/MeOH). The purified product thus obtained was mixed with EtOH (5 ml), and L-tartaric acid (41.0 mg) were added thereto, followed by stirring at 80° C. for 1 hour, and then stirring at room temperature for 1 hour. The solid was collected by filtration, washed with EtOH, and then dried at 50° C. under reduced pressure to obtain 2-fluoro-3-[4-(6-oxo-1,6-dihydropyridin-3-yl)piperazin-1-yl]benzyl carbamimidoylcarbamate L-tartrate (125 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was mixed with CHCl3/MeOH, and basic silica gel
  3. additionwas added
  4. concentrationby concentrating under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (CHCl3/MeOH)
  6. customThe purified product thus obtained
  7. additionwere added
  8. stirringby stirring at 80° C. for 1 hour
  9. stirringstirring at room temperature for 1 hour
  10. filtrationThe solid was collected by filtration
  11. washwashed with EtOH
  12. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-81246bc924d04de3a1a13cde0afe30a7
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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