Hydrochloric Acid → HCID 58405374, compound

HRID 44893Notes

Reaction equation

HRID 44893 reaction equation
Cl.[CH2:2]([CH:4]1[N:13]([C:14]2[CH:15]=[N:16][N:17](COCC[Si](C)(C)C)[CH:18]=2)[C:12]2[N:11]=[C:10]([N:27]3[CH:31]=[CH:30][N:29]=[C:28]3[C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[N:9]=[CH:8][C:7]=2[N:6]([CH3:39])[C:5]1=[O:40])[CH3:3]>O1CCOCC1.CO>[CH2:2]([CH:4]1[N:13]([C:14]2[CH:15]=[N:16][NH:17][CH:18]=2)[C:12]2[N:11]=[C:10]([N:27]3[CH:31]=[CH:30][N:29]=[C:28]3[C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[N:9]=[CH:8][C:7]=2[N:6]([CH3:39])[C:5]1=[O:40])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58405596HCID 58405596, compound

Product 1

HCID 58405374HCID 58405374, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

HCl (2 mL of a 4 N solution in dioxane) was added to a solution of 7-ethyl-2-(2-(4-fluorophenyl)-1H-imidazol-1-yl)-5-methyl-8-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)-7,8-dihydropteridin-6(5H)-one (Example 342, 49 mg, 0.0893 mmol) in 2 mL of methanol and the resulting solution was stirred at 60° C. for 2 hours. The mixture was concentrated under vacuum and purified by HPLC to give the title compound. 1H-NMR (CDCl3, 400 MHz): δ: 7.90 (s, 1H), 7.75 (s, 1H), 7.50-7.54 (m, 3H), 7.35 (s, 2H), 7.03-7.07 (m, 2H), 4.59-4.61 (m, 1H), 3.46 (s, 3H), 1.98-2.03 (m, 1H), 1.77-1.84 (m, 1H), 0.84 (t, 3H, J=7.4 Hz); LCMS: 418.9 m/z (M+H)+; ret. Time: 3.98 min (Analytical Method C).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-64c73ff091e041909d98f1de3a3ba6cd
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

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