Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | L-Tyrosine | HCID 6057 | — |
| Reactant | 2-Chloro-6-methylphenol | HCID 6898 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 18007103 | HCID 18007103 | — |
| Reactant | HCID 178420739 | HCID 178420739 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18007097 | HCID 18007097 | — |
Reaction Steps
A mixture of 4-chloro-7,8-dimethoxyimidazo[1,5-a]quinoxaline, prepared as described in U.S. application Ser. No. 09/097,338, “Imidazoquinoxaline Protein Tyrosine Kinase Inhibitors,” filed by Joel C. Barrish et al. concurrently herewith (Attorney Docket No. QA202b) (20 mg, 0.076 mmol), potassium carbonate (52 mg, 0.38 mmol) and 2-chloro-6-methylphenol (13 mg, 0.091 mmol) in 0.5 mL of dry DMF was heated at 80° C. overnight. Upon cooling, the solvent was removed under reduced pressure and the residue was purified by preparative HPLC to give 9.0 mg of the title compound as a tan solid. HPLC Ret. time=4.075 min (HPLC Conditions: 0% B to 100% B; 4 minute gradient; 2 minute hold; 4 mL/min.; 254 nm; YMC S5 C18 Rapid Resolution column 4.6×50 mm; A: 90% H2O−10% MeOH−0.2% H3PO4; B: 10% H2O−90% MeOH−0.2% H3PO4).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06635626B1 |
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| Source dataset | uspto-grants-2003_10 |
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| ORD ID | ord-b3a5184be5034201b5e1161771141bf6 |
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| Source note | uspto-grants-2003_10 |
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