2-amino-N-propan-2-ylbenzamide

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

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

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

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

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

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

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

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vessel was charged with 2,4-dichloro-5-methylpyrimidine (5.0 g, 28 mmol), 2-amino-N-(1-methyethyl)benzamide (5.46 g, 34.3 mmol), di-isopropyl-ethylamine (7.0 mL, 42 mmol) and 2-(methyloxy)ethanol (30 mL) and sealed and heated with stirring at 130° C. for 36 hours. The reaction was cooled to room temperature and 50 mL water was added dropwise to afford a milky white solution, which was heated to 100° C. to induce precipitation. The solution was cooled and the solid collected by filtration. The collected solid was washed successively with water (2×50 mL) and hexane (3×50 mL). After drying, a white solid was collected (6.56 g, 77% yield) and identified as 2-[(2-chloro-5-methyl-4-pyrimidinyl)amino]-N-(1-methyethyl)benzamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.51 (1H, s) 8.56-8.63 (2H, m) 8.15 (1H, s) 7.81 (1H, dd, J=7.83, 1.52 Hz) 7.58 (1H, dd, J=15.66, 1.52 Hz) 7.17 (1H, dd, J=15.28, 1.14 Hz) 4.13 (1H, dd, J=14.02, 6.69 Hz) 2.18 (3H, s) 1.18 (6H, d, J=6.57 Hz). sealed heated The reaction was cooled to room temperature to afford a milky white solution, which was heated to 100° C. precipitation The solution was cooled the solid collected by filtration The collected solid was washed successively with water (2×50 mL) and hexane (3×50 mL) After drying a white solid was collected (6.56 g, 77% yield)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A round-bottomed flask was charged with 2,4,5-trichloropyrimidine (2.0 g, 6.8 mmol), 2-amino-N-(1-methylethyl)benzamide (1.2 g, 7.1 mmol), di-isopropyl-ethylamine (1.4 mL, 8.1 mmol) and 30 mL isopropanol. The flask was fitted with a reflux condenser and the reaction was heated to reflux and stirred for 18 h. A white solid appeared in the reaction mixture. The reaction was cooled to 0° C. and filtered and solid was washed with diethyl ether to afford 2-[(2,5-dichloro-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide (2.0 g, 90%) The flask was fitted with a reflux condenser the reaction was heated to reflux filtered solid was washed with diethyl ether

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

Procedure: A round-bottomed flask was charged with isatoic anhydride (5.0 g, 0.030 mol) and 30 mL water. Isopropylamine (4.64 mL, 0.049 mol) was added slowly to the reaction mixture. The product precipitated from the reaction mixture. After 1 h, the reaction mixture was filtered and washed with water to give 4.12 g (71% yield) of a white solid The product precipitated from the reaction mixture the reaction mixture was filtered washed with water

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

Procedure: 2-Amino-N-isopropylbenzamide (prepared from isopropylamine and isatoic anhydride, using the methods described in Example 17) and CMI were reacted using conditions described in the general procedure for CMI coupling to give 2-[(4,5-dihydro-1H-imidazol-2-ylmethyl)amino]-N-isopropylbenzamide. were reacted

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A vessel was charged with 2,4-dichloro-5-methylpyrimidine (5.0 g, 28 mmol), 2-amino-N-(1-methylethyl)benzamide (5.46 g, 34.3 mmol), di-isopropyl-ethylamine (7.0 mL, 42 mmol) and 2-(methyloxy)ethanol (30 mL) and sealed and heated with stirring at 130° C. for 36 hours. The reaction was cooled to room temperature and 50 mL water was added dropwise to afford a milky white solution, which was heated to 100° C. to induce precipitation. The solution was cooled and the solid collected by filtration. The collected solid was washed successively with water (2×50 mL) and hexane (3×50 mL). After drying, a white solid was collected (6.56 g, 77% yield) and identified as 2-[(2-chloro-5-methyl-4-pyrimidinyl)amino]-N-(1-methylethyl)benzamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.51 (1H, s) 8.56-8.63 (2H, m) 8.15 (1H, s) 7.81 (1H, dd, J=7.83, 1.52 Hz) 7.58 (1H, dd, J=15.66, 1.52 Hz) 7.17 (1H, dd, J=15.28, 1.14 Hz) 4.13 (1H, dd, J=14.02, 6.69 Hz) 2.18 (3H, s) 1.18 (6H, d, J=6.57 Hz). sealed heated The reaction was cooled to room temperature to afford a milky white solution, which was heated to 100° C. precipitation The solution was cooled the solid collected by filtration The collected solid was washed successively with water (2×50 mL) and hexane (3×50 mL) After drying a white solid was collected (6.56 g, 77% yield)