Hydrochloric Acid → HCID 178461926, compound

HRID 243355Notes

Reaction equation

HRID 243355 reaction equation
Cl.[Br:2][C:3]1[C:8]2[N:9]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:10]([C@@H:12]([NH:14][C:15]3[N:23]=[CH:22][N:21]=[C:20]4[C:16]=3[N:17]=[CH:18][N:19]4C3CCCCO3)[CH3:13])=[N:11][C:7]=2[CH:6]=[CH:5][C:4]=1[F:36]>O1CCOCC1.CO>[Br:2][C:3]1[C:8]2[N:9]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:10]([C@@H:12]([NH:14][C:15]3[N:23]=[CH:22][N:21]=[C:20]4[C:16]=3[N:17]=[CH:18][NH:19]4)[CH3:13])=[N:11][C:7]=2[CH:6]=[CH:5][C:4]=1[F:36]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68157939[(S)-1-(7-Bromo-6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine

Product 1

HCID 178461926HCID 178461926, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

4N HCl in dioxane (0.5 mL) was added to a solution of [(S)-1-(7-bromo-6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine (128 mg, 0.24 mmol) in MeOH (3 mL) and the mixture stirred at RT for 30 min. The volatiles were removed in vacuo and the resulting residue purified by HPLC (Phenomenex Gemini 5 μm C18 on a 25 min gradient 10-90% 0.1% HCO2H in acetonitrile/water) to afford 178 (88 mg, 81%). LCMS (Method K): RT 3.82 min [M+H]+ 451.9/453.8. 1H NMR (DMSO-d6, 400 MHz): δ 8.19-7.86 (3H, m), 7.70 (1H, dd, J=8.75, 4.59 Hz), 7.64-7.33 (5H, m), 7.26 (1H, t, J=9.22 Hz), 5.22 (1H, s), 1.56 (3H, d, J=6.87 Hz)

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue purified by HPLC (Phenomenex Gemini 5 μm C18 on a 25 min gradient 10-90% 0.1% HCO2H in acetonitrile/water)

Sources & evidence

ORD record
ord-e5fe0017f6924555822c5e2db2f35408
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…