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Table 2 names some of the specific intermediates unique to this work. A solution of compound C102 (200 mg 0.73 mmol) in DCM (3.6 mL) was treated with Et Step 4. The mixture was stirred for about 15 min at about 25 °C, then cooled to about 0 °C and treated with NFSI (12.1 g, 38 mmol).

The heteroaryl can be optionally substituted, as appropriate, by 1 to 5 suitable substituents as defined herein such as fluoro, chloro, deutero, cyano, trifluoromethyl, (C The term "heteroaryl" also includes fused ring systems having one or two rings wherein such rings may be fused, wherein fused is as defined above. Typically, a compound of the invention is administered in an amount effective to treat a condition as described herein. A mixture of DCM (1 mL) and TFA (1 mL) was added and the mixture was kept at about 25 °C for about 2 h. It was then concentrated to dryness to provide the title compound L97. Yield: 2.6 g (61 %).

Cxxiv Scheme 6 illustrates a method for the preparation of compounds of Formula A. lo[1 ,2- cloxazol-5(3H)-one (C127). Synthesis of 6-methoxy-4-oxo-3,4-dihvdroquinazoline-7-carbonitrile (C17). The reactants A were prepared as described in this specification. This process was repeated twice more, after which the filter cake was washed with MTBE (0.5 L) and dried under vacuum at about 60 °C to provide the title compound C11 . Preparation 45: (1 R,4S,5S,6S)-6-fluoro-4-(hvdroxymethyl)-3-azabicyclor3.1.Olhe The reaction mixture was maintained for about 10 minutes at about -78 °C, then allowed to warm to about 25 °C for about 25 minutes. Preparation 51 : (1 S,4S,5R)-1-fluoro-4-(hvdroxymethyl)-3-azabicyclor3.1.0lhexan

Upon drying, 250 g of compound C6 was obtained. The aqueous phase was extracted with EtOAc, and the combined EtOAc extracts were dried over Na Step 4. Yield 1.1 g (38%). High performance liquid preparative chromatography using a 0.1 % trifluoroacetic acid in water with acetonitrile gradient on a Phenomenex Luna phenyl-hexyl column was utilized to isolate compounds from the above preparation. Preparation 50: (1 R,4S,5S)-4-(hvdroxymethyl)-5-methyl-3-azabicyclor3.1.01hexan Synthesis of (3R,7aS)-6-hvdroxy-3-(4-methoxyphenyl)tetrahvdropyrrolo[1 ,2-cloxazol- 5(3H)-one (C40). The invention also provides for pharmaceutical compositions comprising the compounds, methods of using the compounds, combination therapies utilizing the compounds and other therapeutic agents and methods of preparing the compounds. , sterile injectable aqueous or oleaginous suspensions) may be formulated according to the known art using suitable dispersing, wetting agents, and/or suspending agents. For use in medicine, the salts of the compounds of this invention are nontoxic "pharmaceutically acceptable salts." A suspension of 1- benzyl 5-methyl (5S)-2-oxoimidazolidine-1 ,5-dicarboxylate (CAS 168399-08-4, 325 mg, 1.2 mmol) and 10% Pd/C (33 mg) in MeOH (4.7 mL) was shaken under a hydrogen atmosphere at about 25 °C for about 5.5 h. The mixture was filtered and concentrated to afford the title compound C145. Step 2: Synthesis of (1 S.3aS.6aR)-di-tert-butyl 1 -(((tert-butyldimethylsilyl)oxy)methyl)-3- oxotetrahvdropyrrolo[3,4-clpyrrole-2,5(1 H,3H)-dicarboxylate (C149). Products were generally dried under vacuum before being carried on to further reactions or submitted for biological testing.

30. A solution of compound C41 (430 mg, 1.6 mmol) in AcOH (8 mL) and water (2 mL) was stirred at about 75 °C for about 30 min. Alternatively, pharmaceutically acceptable salts are suitable for medical applications because of their greater aqueous solubility relative to the parent compound. et al. Yield 38 mg (86%) Synthesis of (5S)-3-fluoro-5-(hvdroxymethyl)pyrrolidin-2-one (L2). Formulation of drugs is discussed in, for example, Hoover, John E., Remington's Pharmaceutical Sciences, Mack Publishing Co., Easton, Pennsylvania, 1975; Liberman et al., Eds. A solution of compound C105 (578 mg, 1.7 mmol) in THF (15 mL) was treated with tert-butyllithium solution (1.7 M, 1.32 mL) at about - 78 °C. This method provides for the alkylation of a compound of Formula A with a compound of Formula B (wherein the R Scheme 3 illustrates a method for the preparation of compounds of Formula A, wherein Y = N and X = CH, as illustrated above. The reaction mixture was heated at about 90 °C for about 45 min. 7. Female C57/BL6 mice, 8 to 10 weeks old, are orally administered either vehicle or formulated IRAK-4 compound 1 hour prior to the challenge. 1.0lhexan-2- one (L80). After stirring for about 10 minutes, the solution was cooled to about -70 °C, and a solution of compound C54 (235 g, 1.17 mol) in THF (588 ml.)

This dosing regimen was optimized to achieve robust skin inflammation in mice as measured by increased ear thickness. The reaction was extracted with EtOAc and the combined EtOAc extracts were washed with brine, dried over MgS0 Step 1. DAST (0.41 mL, 2.9 mmol) was added dropwise to a solution of compound C81 (0.51 g, 2.2 mmol) in DCM (20 mL) at about -78 °C. The mixture was then cooled to about 25 °C and concentrated under reduced pressure. The mixture of compound C22 and and methyl 6-isopropoxy-4-oxo-1 ,4-dihydroquinoline-5- carboxylate (31 1 g, 1.19 mol) was added to THF (1.55 L) and water (1.55 L).
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