3-hydroxynaphthalene-2-carboxamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetic anhydride (19.2 ml, 200 mmol) was added to a solution of 18 (29.95 g, 160 mmol) in pyridine (32 ml, 400 mmol) and the mixture was maintained at room temperature for 30 minutes. The solid was filtered off, washed with acetone and dried (MgSO4), generating 27.06 g (74%) of 19 as pale yellow crystals, mp 201°-202° C. (lit. 203°-205° C.). The solid was filtered off washed with acetone dried (MgSO4) 27.06 g (74%) of 19 as pale yellow crystals, mp 201°-202° C. (lit. 203°-205° C.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetic anhydride (19.2 ml, 200 mmol) was added to a solution of 18 (29.95 g, 160 mmol) in pyridine (32 ml, 400 mmol) and the mixture was maintained at room temperature for 30 minutes. The solid was filtered off, washed with acetone and dried (MgSO4), generating 27.06 g (74%) of 19 as pale yellow crystals, mp 201°-202° C. (lit. 203°-205° C.). The solid was filtered off washed with acetone dried (MgSO4) 27.06 g (74%) of 19 as pale yellow crystals, mp 201°-202° C. (lit. 203°-205° C.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetic anhydride (19.2 ml, 200 mmol) was added to a solution of 18 (29.95 g, 160 mmol) in pyridine (32 ml, 400 mmol) and the mixture was maintained at room temperature for 30 minutes. The solid was filtered off, washed with acetone and dried (MgSO4), generating 27.06 g (74%) of 19 as pale yellow crystals, mp 201°-202° C. (lit. 203°-205° C.). The solid was filtered off washed with acetone dried (MgSO4) 27.06 g (74%) of 19 as pale yellow crystals, mp 201°-202° C. (lit. 203°-205° C.)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 26 mg (0.083 mmol) of N-[4,8-dimethoxyquinoline-2-yl)carbonyl]-4-piperidone (prepared as described in Example 44), 15.5 mg (0.083 mmol) of 3-hydroxy-2-naphthalenecarboxamide, and 0.020 mL of morpholine in a mixture of 0.2 mL of toluene and 0.6 mL of methanol is refluxed for 20 hr. The reaction mixture is diluted with ethyl acetate, and washed with water, brine, and dried over Na2SO4. After solvent removal by rotoevaporation, the crude product is purified by preparative TLC to give 11 mg (0.023 mmol, 27% yield) of 1′-[4,8-dimethoxyquinoline-2-yl)carbonyl]spiro[2H-naphtho[2,3-e]-1,3-oxazin-2,4′-piperidin]-4-(3H)-one (Compound 159): 1H NMR (DMSO-d6): δ 3.95 (s, 3H), 4.07 (s, 3H), 7.20 (s, 1H), 7.23 (d, 1H), 7.44 (d of d, 1H), 7.55 (m, 3H), 7.67 (d, 1H), 8.04 (d, 1H), 8.46 (s, 1H), and 9.09 ppm (s, 1H). MS m/z: 484.0 (M+H)+, 506.0 (M+Na)+. is refluxed for 20 hr washed with water, brine dried over Na2SO4 After solvent removal by rotoevaporation the crude product is purified by preparative TLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetic anhydride (19.2 ml, 200 mmol) was added to a solution of 18 (29.95 g, 160 mmol) in pyridine (32 ml, 400 mmol) and the mixture was maintained at room temperature for 30 minutes. The solid was filtered off, washed with acetone and dried (MgSO4), generating 27.06 g (74%) of 19 as pale yellow crystals, mp 201°-202° C. (lit. 203°-205° C.). The solid was filtered off washed with acetone dried (MgSO4) 27.06 g (74%) of 19 as pale yellow crystals, mp 201°-202° C. (lit. 203°-205° C.)