2-amino-6-methylbenzamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A mixture of 2-amino-6-methylbenzamide (UK Patent Application No 1,276,359; 5.49 g, 0.0365 mol), 2-ethoxybenzoyl chloride (7.67 g, 0.0415 mol) and pyridine (100 ml) was stirred at room temperature for 20 hours. The solvent was then removed by evaporation under vacuum and the residue dissolved in dichioromethane (200 ml). The solution was washed with saturated aqueous sodium carbonate solution (200 ml) and the aqueous phase back-extracted with further dichioromethane (2×100 ml). The organic solutions were combined, washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml), then dried (Na2SO4) and evaporated under vacuum to give the title compound, which recrystallized from ethyl acetate as a colourless solid (6.86g, 63%), m.p. 166-168° C. The solvent was then removed by evaporation under vacuum the residue dissolved in dichioromethane (200 ml) The solution was washed with saturated aqueous sodium carbonate solution (200 ml) the aqueous phase back-extracted with further dichioromethane (2×100 ml) washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml) dried (Na2SO4) evaporated under vacuum

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

Procedure: A mixture of 2-amino-6-methylbenzamide (UK Patent Application No 1,276,359; 5.49 g, 0.0365 mol), 2-ethoxybenzoyl chloride (7.67 g, 0.0415 mol) and pyridine (100 ml) was stirred at room temperature for 20 hours. The solvent was then removed by evaporation under vacuum and the residue dissolved in dichloromethane (200 ml). The solution was washed with saturated aqueous sodium carbonate solution (200 ml) and the aqueous phase back-extracted with further dichloromethane (2×100 ml). The organic solutions were combined, washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml), then dried (Na2SO4) and evaporated under vacuum to give the title compound, which recrystallized from ethyl acetate as a colorless solid (6.86 g, 63%), m.p. 166°-168° C. Found: C,68.28; H,5.97; N,9.42. C17H18N2O3 requires C;68.44; H,6.08; N,9.39%. The solvent was then removed by evaporation under vacuum the residue dissolved in dichloromethane (200 ml) The solution was washed with saturated aqueous sodium carbonate solution (200 ml) the aqueous phase back-extracted with further dichloromethane (2×100 ml) washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml) dried (Na2SO4) evaporated under vacuum

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 9.6 g of 6-methylanthranilamide and 12.6 g of 2-bromo-4,5-dimethylthiazole were stirred for 12 hours at 150° C. After working up in the conventional manner there was obtained 11.9 g (81%) of the above compound; m.p. 278°-280° C.

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: While stirring, 22.5 g of 6-methylanthranilamide was added to 18 g of 2-chlorothiazole. The reaction mixture was heated over a 20-minute period to 140° C. and stirred for 4 hours. Water was added to the reaction mixture, and a pH of 10 was set by adding 25% strength ammonia solution. Working up in the conventional manner gave 22.3 g (69%) of compound 3; m.p. 148°-150° C. stirred for 4 hours

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

Procedure: Using General Protocol II and starting with 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (2.79 g, 8.2 mmol) and 2-amino-6-methylbenzamide (0.830 g, 5.46 mmol), 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-methylbenzamide was isolated as a yellow solid (0.960 g, 38% yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.32 (s, 3 H), 2.36 (s, 3 H), 6.49 (s, 1 H), 7.18-7.24 (m, 2 H), 7.30 (s, 1 H), 7.44-7.47 (m, 4 H), 7.56 (d, J=4.03 Hz, 1 H), 7.95 (d, J=8.43 Hz, 2 H).

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

Procedure: To a solution of 2-amino-6-methylbenzamide (1.28 g, 8.52 mmol) and triethylamine (1.03 g, 10.2 mmol) in THF (30 mL) was added dropwise ethyl chloroglyoxylate (1.28 g, 9.38 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hr, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was suspended in diisopropyl ether-ethanol, and the insoluble material was collected by filtration to give ethyl ((2-(aminocarbonyl)-3-methylphenyl)amino)(oxo)acetate as a white powder (1.85 g, 87%). cooling extracted with ethyl acetate The organic layer was washed with saturated brine dried over sodium sulfate concentrated under reduced pressure the insoluble material was collected by filtration

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

Procedure: A mixture of 2-amino-6-methylbenzamide (UK Patent Application No 1,276,359; 5.49 g, 0.0365 mol), 2-ethoxybenzoyl chloride (7.67 g, 0.0415 mol) and pyridine (100 ml) was stirred at room temperature for 20 hours. The solvent was then removed by evaporation under vacuum and the residue dissolved in dichioromethane (200 ml). The solution was washed with saturated aqueous sodium carbonate solution (200 ml) and the aqueous phase back-extracted with further dichioromethane (2×100 ml). The organic solutions were combined, washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml), then dried (Na2SO4) and evaporated under vacuum to give the title compound, which recrystallized from ethyl acetate as a colourless solid (6.86g, 63%), m.p. 166-168° C. The solvent was then removed by evaporation under vacuum the residue dissolved in dichioromethane (200 ml) The solution was washed with saturated aqueous sodium carbonate solution (200 ml) the aqueous phase back-extracted with further dichioromethane (2×100 ml) washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml) dried (Na2SO4) evaporated under vacuum

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

Procedure: A mixture of 2-amino-6-methylbenzamide (UK Patent Application No 1,276,359; 5.49 g, 0.0365 mol), 2-ethoxybenzoyl chloride (7.67 g, 0.0415 mol) and pyridine (100 ml) was stirred at room temperature for 20 hours. The solvent was then removed by evaporation under vacuum and the residue dissolved in dichloromethane (200 ml). The solution was washed with saturated aqueous sodium carbonate solution (200 ml) and the aqueous phase back-extracted with further dichloromethane (2×100 ml). The organic solutions were combined, washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml), then dried (Na2SO4) and evaporated under vacuum to give the title compound, which recrystallized from ethyl acetate as a colorless solid (6.86 g, 63%), m.p. 166°-168° C. Found: C,68.28; H,5.97; N,9.42. C17H18N2O3 requires C;68.44; H,6.08; N,9.39%. The solvent was then removed by evaporation under vacuum the residue dissolved in dichloromethane (200 ml) The solution was washed with saturated aqueous sodium carbonate solution (200 ml) the aqueous phase back-extracted with further dichloromethane (2×100 ml) washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml) dried (Na2SO4) evaporated under vacuum

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

Procedure: A mixture of 2-amino-6-methylbenzamide (UK Patent Application No 1,276,359; 5.49 g, 0.0365 mol), 2-ethoxybenzoyl chloride (7.67 g, 0.0415 mol) and pyridine (100 ml) was stirred at room temperature for 20 hours. The solvent was then removed by evaporation under vacuum and the residue dissolved in dichloromethane (200 ml). The solution was washed with saturated aqueous sodium carbonate solution (200 ml) and the aqueous phase back-extracted with further dichloromethane (2×100 ml). The organic solutions were combined, washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml), then dried (Na2SO4) and evaporated under vacuum to give the title compound, which recrystallized from ethyl acetate as a colorless solid (6.86 g, 63%), m.p. 166°-168° C. Found: C,68.28; H,5.97; N,9.42. C17H18N2O3 requires C;68.44; H,6.08; N,9.39%. The solvent was then removed by evaporation under vacuum the residue dissolved in dichloromethane (200 ml) The solution was washed with saturated aqueous sodium carbonate solution (200 ml) the aqueous phase back-extracted with further dichloromethane (2×100 ml) washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml) dried (Na2SO4) evaporated under vacuum