Hydrochloric Acid → HCID 178463570, compound

HRID 243356Notes

Reaction equation

HRID 243356 reaction equation
Cl.[Cl: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>[Cl: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]([CH: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 68157935HCID 68157935, compound

Product 1

HCID 178463570HCID 178463570, compoundYield 69.2%

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-chloro-6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine (166 mg, 0.34 mmol) in MeOH (5 mL) and the mixture was stirred at RT for 1 h. The volatiles were removed in vacuo and the resulting residue was purified by HPLC (Phenomenex Gemini 5 μm C18 on a 25 min gradient 10-90%, 0.1% HCO2H in acetonitrile/water) to afford 179 (96 mg, 69%). LCMS (Method K): RT 3.80 min [M+H]+ 408.0/409.9/411.08. 1H NMR (DMSO-d6, 400 MHz): δ 8.22-7.83 (3H, m), 7.69-7.34 (6H, m), 7.33-7.24 (1H, t, J=9.50 Hz), 5.25 (1H, s), 1.56 (3H, d, J=6.88 Hz)

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue was 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-43fe6d1464e64124958251dae4d2669e
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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