Ammonia → 3-Bromo-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-8-ylamine

HRID 449035Notes

Reaction equation

HRID 449035 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10](Cl)[C:5]2=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[N:3]=1.[NH3:25].CC(O)C>>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH2:25])[C:5]2=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[N:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 3776IsopropanolHCID 866360333-Bromo-8-chloro-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazine

Product 1

HCID 669155513-Bromo-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-8-ylamine

Procedure

3-Bromo-8-chloro-1-(4-phenoxy-phenyl)-imidazo[1,5-a]pyrazine (2.05 g, 5.0 mmol) and NH3 in iPrOH (9 M, 20 mL, 180 mmol) in a bomb apparatus were heated at 110° C. for 24 h. Cooled to rt., and evaporated. The residue was dissolved in EtOAc (20 mL), washed with water (10 mL) and dried (Na2SO4). Evaporation of solvent gave a residue, which was triturated with diisopropyl ether (30 mL). 1H NMR (DMSO-d6, 400 MHz), δ 6.23 (bs, 2H), 7.09-7.19 (m, 6H), 7.39-7.43 (m, 3H), 7.58 (d, J=8.4 Hz, 2H).

Workup

  1. custom, and evaporated
  2. dissolutionThe residue was dissolved in EtOAc (20 mL)
  3. washwashed with water (10 mL)
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of solvent
  6. customgave a residue, which
  7. customwas triturated with diisopropyl ether (30 mL)

Sources & evidence

ORD record
ord-d932dee7004741b891528a8362fb0664
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

Loading…