N,2,2-trimethylpropan-1-amine

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:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-(6-chloro-5-cyano-3-fluoro-pyridin-2-ylamino)-N-methoxy-4-methyl-benzamide (55.6 mg, 0.166 mmol), N-methyl-neopentylamine (70 mg, 0.511 mmol), diisopropylethylamine (0.1 mL) and potassium fluoride (12 mg) in DMSO (1 mL) was heated to 150° C. overnight. The product (3.9 mg, 5.9%) was isolated after purification by HPLC. C21H26FN5O2 MS m/e=400 (M+H).

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-(6-chloro-5-cyano-3-fluoro-pyridin-2-ylamino)-N-methoxy-4-methyl-benzamide (55.6 mg, 0.166 mmol), N-methyl-neopentylamine (70 mg, 0.511 mmol), diisopropylethylamine (0.1 mL) and potassium fluoride (12 mg) in DMSO (1 mL) was heated to 150° C. overnight. The product (3.9 mg, 5.9%) was isolated after purification by HPLC. C21H26FN5O2 MS m/e=400 (M+H).

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Methyl neopentyl amine (0.781 g, 5.68 mmol) and 3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid (1.37 g, 4.73 mmol) were combined in DME (13 mL). DIPEA (3.47 mL, 19.87 mmol) and BOP-CI (2.53 g, 9.93 mmol) were added. The mixture was stirred at 60° C. for 1 h. The reaction mixture was diluted with EtOAc (50 mL) and washed with aqueous 1M KHSO4 (3×20 mL), aqueous saturated NaHCO3 (3×20 mL) and brine (2×20 mL) before drying on Na2SO4 and concentration in vacuo to give an oil. The product was dissolved by heating in i-Pr2O and left to cool for 16 h. A solid had formed which was filtered off and washed with i-Pr2O (2×5 mL) to give a light yellow solid. The filtrate was combined with the residue and purified using column chromatography (silica, gradient heptane/EtOAc 95:5−>7:3) to give the desired product (604 mg, 34%) as a yellow solid. The mother liquor was concentrated in vacuo and triturated with heptane to give another batch of the desired product (271 mg, 15%) as a white solid. washed with aqueous 1M KHSO4 (3×20 mL), aqueous saturated NaHCO3 (3×20 mL) and brine (2×20 mL) before drying on Na2SO4 and concentration in vacuo to give an oil The product was dissolved left to cool for 16 h A solid had formed which was filtered off washed with i-Pr2O (2×5 mL) to give a light yellow solid purified

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:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-(6-chloro-5-cyano-3-fluoro-pyridin-2-ylamino)-N-methoxy-4-methyl-benzamide (55.6 mg, 0.166 mmol), N-methyl-neopentylamine (70 mg, 0.511 mmol), diisopropylethylamine (0.1 mL) and potassium fluoride (12 mg) in DMSO (1 mL) was heated to 150° C. overnight. The product (3.9 mg, 5.9%) was isolated after purification by HPLC. C21H26FN5O2 MS m/e=400 (M+H).