3-[(dimethylamino)methyl]aniline

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:; See reaction.notes.procedure_details.

Procedure: 3-[(3,4-Dimethoxy-benzoylamino)-methyl]-benzoic acid (40 mg, 0.127 mmol), prepared as described in Example 8, was combined with EDC (38.3 mg, 0.2 mmol) and HOBt (24.3 mg, 0.18 mmol) in a reaction vial, and DMF (1 mL) was added followed by N-methylmorpholine (0.025 mL, 0.22 mmol). The resulting mixture was agitated for 1 h, then 3-dimethylaminomethyl-phenylamine (25.5 mg, 0.17 mmol) was added as a solution in DMF (0.5 mL), and the resulting mixture was agitated overnight. The product was purified directly by preparative HPLC using an acetonitrile/water/formic acid gradient providing the title compound as a formate salt (40 mg, 70% yield), MS analysis electrospray, 448 (M+H). was added the resulting mixture was agitated overnight The product was purified directly by preparative HPLC

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

Procedure: Using 1,2-dihydro-2-methyl-1-oxo-4-phenyl-3-isoquinoline acetic acid, diphenylphosphoryl azide and 3-(dimethylaminomethyl)aniline, the reaction was carried out by substantially the same procedure as in Method B of Example 1, followed by treatment of the product with hydrogen chloride in ethyl acetate to give the title compound as a white powdery product. NMR (200 MHz,DMSO-d6) ppm: 2.67(3H,s), 2.69(3H,s), 3.64(3H,s), 4.17(4H,m), 6.9-7.2(4H,m), 7.3-7.7(9H,m), 8.32(1H,m), 9.09(1H,bs)

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

Procedure: Using 1,2-dihydro-2-methyl-1-oxo-4-phenyl-3-isoquinoline acetic acid, diphenylphosphoryl azide and 3-(dimethylaminomethyl)aniline, the reaction was carried out by substantially the same procedure as in Method B of Example 1, followed by treatment of the product with hydrogen chloride in ethyl acetate to give the title compound as a white powdery product. NMR (200 MHz,DMSO-d6) ppm: 2.67(3H,s), 2.69(3H,s), 3.64(3H,s), 4.17(4H,m), 6.9-7.2(4H,m), 7.3-7.7(9H,m), 8.32(1H,m), 9.09(1H,bs)

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

Procedure: The title compound is prepared as described in Example 152A but using 3-dimethylaminomethyl-phenylamine, 6-chloro-pyrimidin-4-ylamine, and stirring the reaction mixture for 2 h at 150° C. The crude product is purified by trituration in diethyl ether followed by silica gel column chromatography (DCM/MeOH+1% NH3aq, 92:8) of the resulting beige solid to afford the title compound as a white solid. ESI-MS: 242.1 [MH]−; tR=0.95 min (purity: 100%, gradient J); TLC: Rf=0.11 (DCM/MeOH+1% NH3aq, 92:8). The title compound is prepared The crude product is purified by trituration in diethyl ether

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

Procedure: The title compound is prepared as described in Example 152A but using 3-dimethylaminomethyl-phenylamine, 6-chloro-pyrimidin-4-ylamine, and stirring the reaction mixture for 2 h at 150° C. The crude product is purified by trituration in diethyl ether followed by silica gel column chromatography (DCM/MeOH+1% NH3aq, 92:8) of the resulting beige solid to afford the title compound as a white solid. ESI-MS: 242.1 [MH]−; tR=0.95 min (purity: 100%, gradient J); TLC: Rf=0.11 (DCM/MeOH+1% NH3aq, 92:8). The title compound is prepared The crude product is purified by trituration in diethyl ether

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound is prepared as described in Example 143A but using 3-dimethylaminomethyl-phenylamine (334 mg, 2.20 mmol, 1 eq.), (6-chloro-pyrimidin-4-yl)-ethyl-amine (Example 143B) and stirring the reaction mixture for 3 h at 160° C. Purification of the crude product by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1) followed by trituration of the resulting solid in diethyl ether, affords 335 mg of the title compound as a beige solid: ESI-MS: 272.1 [MH]+; tR=1.18 min (purity: 100%, gradient J); TLC: Rf=0.16 (DCM/MeOH+1% NH3aq, 9:1). The title compound is prepared Purification of the crude product by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1)

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound is prepared as described in Example 143A but using 3-dimethylaminomethyl-phenylamine (334 mg, 2.20 mmol, 1 eq.), (6-chloro-pyrimidin-4-yl)-ethyl-amine (Example 143B) and stirring the reaction mixture for 3 h at 160° C. Purification of the crude product by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1) followed by trituration of the resulting solid in diethyl ether, affords 335 mg of the title compound as a beige solid: ESI-MS: 272.1 [MH]+; tR=1.18 min (purity: 100%, gradient J); TLC: Rf=0.16 (DCM/MeOH+1% NH3aq, 9:1). The title compound is prepared Purification of the crude product by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1)