L-Tyrosine → HCID 18007097, compound

HRID 988079Notes

Reaction equation

HRID 988079 reaction equation
Cl[C:2]1[C:3]2[N:4]([CH:16]=[N:17][CH:18]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=2.N1C2C3N=CC=NC=3C=CC=2N=C1.N[C@H](C(O)=O)CC1C=CC(O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[Cl:51][C:52]1[CH:57]=[CH:56][CH:55]=[C:54]([CH3:58])[C:53]=1[OH:59]>CN(C=O)C>[Cl:51][C:52]1[CH:57]=[CH:56][CH:55]=[C:54]([CH3:58])[C:53]=1[O:59][C:2]1[C:3]2[N:4]([CH:16]=[N:17][CH:18]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=2

Participants

7

Reactant 5

HCID 6057L-TyrosineHCID 68982-Chloro-6-methylphenolHCID 11430Potassium CarbonateHCID 18007103HCID 18007103, compoundHCID 178420739HCID 178420739, compound

Product 1

HCID 18007097HCID 18007097, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  1. customprepared
  2. temperatureUpon cooling
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b3a5184be5034201b5e1161771141bf6
Source dataset
uspto-grants-2003_10
Patent number
US06635626B1

Reaction notes

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