HCID 86610046, compound → HCID 86610045, compound

HRID 352341Notes

Reaction equation

HRID 352341 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][O:10][CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[NH:21][CH:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][NH:30]C(=O)OC(C)(C)C)[CH2:24][CH2:23]2)[CH:5]=[CH:4][CH:3]=1>CC(O)C.Br.C(O)(=O)C>[NH2:30][CH2:29][CH2:28][N:25]1[CH2:24][CH2:23][CH:22]([NH:21][C:13]2[N:12]([CH2:11][O:10][CH2:9][CH2:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=3)[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=2)[CH2:27][CH2:26]1

Participants

4

Reactant 1

HCID 86610046HCID 86610046, compound

Product 1

HCID 86610045HCID 86610045, compoundYield 18.7%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

A mixture of compound (7) (0.0026 mol) in 2-propanol (30 ml) and HBr/acetic acid (2 ml) was stirred and refluxed for 90 minutes and then cooled. The solvent was evaporated. The residue was taken up in CH2Cl2 and H2O. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent. CH2Cl2/(CH3OH/NH3) 90/10). The pure fractions were collected and the solvent was evaporated. The residue was suspended in diisopropyl ether. The precipitate was filtered off and dried. This fraction was purified again by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 90/10). The pure fractions were collected and the solvent was evaporated. The residue was suspended in diisopropyl ether. The precipitate was filtered off and dried, yielding 0.23 g of (±)-N-[1-(2-aminoethyl)-4-piperidinyl]-1-[(6-bromo-2-pyridinyl)ethoxymethyl]-1H-benzimidazol-2-amine (compound 9).

Workup

  1. temperaturerefluxed for 90 minutes
  2. temperaturecooled
  3. customThe solvent was evaporated
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent. CH2Cl2/(CH3OH/NH3) 90/10)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. filtrationThe precipitate was filtered off
  12. customdried
  13. customThis fraction was purified again by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 90/10)
  14. customThe pure fractions were collected
  15. customthe solvent was evaporated
  16. filtrationThe precipitate was filtered off
  17. customdried

Sources & evidence

ORD record
ord-5a03f7003ca04ed086b60c8fc76fad1c
Source dataset
uspto-grants-2004_06
Patent number
US06747028B1

Reaction notes

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