Acetic Acid → HCID 85618866, compound

HRID 1587670Notes

Reaction equation

HRID 1587670 reaction equation
[BrH:1].Cl[C:3]1[N:8]=[C:7]([CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)[CH:6]=[N:5][CH:4]=1.[C:17](=[O:20])([O-:19])[O-].[K+].[K+].[C:23]([OH:26])(=[O:25])C>>[C:23]([OH:26])(=[O:25])[C:17]([OH:19])=[O:20].[Br:1][C:3]1[N:8]=[C:7]([CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)[CH:6]=[N:5][CH:4]=1.[C:23]([OH:26])(=[O:25])[C:17]([OH:19])=[O:20].[C:23]([OH:26])(=[O:25])[C:17]([OH:19])=[O:20].[Br:1][C:3]1[N:8]=[C:7]([CH:9]2[CH:14]3[CH2:15][CH2:16][N:11]([CH2:12][CH2:13]3)[CH2:10]2)[CH:6]=[N:5][CH:4]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 11430Potassium Carbonate2×HCID 132658HCID 132658, compound

Product 1

HCID 85618866HCID 85618866, compound

Procedure

Hydrogen bromide in acetic acid (5.0 mL of a 30% solution) was added to 3-(6-chloropyrazin-2-yl)-1-azabicyclo[2.2.2]octane (613 mg, 2.74 mmol; EPA 327155) and the solution was stirred at room temperature for 3.5 days. The mixture was poured into 0.5M potassium carbonate (75 mL) then further basified with solid potassium carbonate and extracted with dichloromethane (five times). The solvent was evaporated and the residue redissolved in hydrogen bromide/acetic acid (5.0 mL) and left stirring for 14 hours. The mixture was worked up as described above and crude product purified by column chromatography on silica using 10% methanol in dichloromethane containing 1% ammonia to afford the title compound free base (289 mg, 39%) as a colourless oil. The sesquioxalate salt had mp 173°-177° C. (dec) (methanol). MS, m/z 267 for M+ of free base. (Found: C, 41.70; H, 4.29; N, 10.40; Br, 20.32. C11H14BrN3.1.5C2H2O4 requires C, 41.70; H, 4.25; N, 10.42; Br, 19.82%).

Workup

  1. extractionextracted with dichloromethane (five times)
  2. customThe solvent was evaporated
  3. dissolutionthe residue redissolved in hydrogen bromide/acetic acid (5.0 mL)
  4. waitleft
  5. stirringstirring for 14 hours
  6. customcrude product purified by column chromatography on silica using 10% methanol in dichloromethane containing 1% ammonia

Sources & evidence

ORD record
ord-cdd92b6cfce6419cbe26cfb7cf009628
Source dataset
uspto-grants-1993_06
Patent number
US05219849

Reaction notes

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