pentan-2-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:25.01; pressure:100.03; stir:

Conditions: temp:25.01; pressure:100.03; stir:

Conditions: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-chloro-8-methoxy-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (40 mg) in ethylene glycol (1.5 mL) was added 2-aminopentane (0.16 mL) and the mixture was heated in a microwave at 170° C. for 2×30 mins. A further portion of 2-aminopentane (0.08 mL) was added and the reaction was heated in a microwave at 180° C. for 30 mins. The mixture was taken up in EtOAc (15 mL) and was washed with water (3×15 mL). The organics were separated, dried over MgSO4, filtered and concentrated in vacuo to give a brown residue. This was taken up in DCM and concentrated in a vacuum oven to give the title compound as a brown solid (18 mg). the reaction was heated in a microwave at 180° C. for 30 mins was washed with water (3×15 mL) The organics were separated dried over MgSO4 filtered concentrated in vacuo to give a brown residue concentrated in a vacuum oven

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

Procedure: A mixture of 3-chloro-6-(methylsulfonyl)-2,4-di-nitrotoluene (10.0 g., 0.034 mole) and 2-aminopentane (6.1 g. 0.07 mole) is refluxed in benzene (75 ml.) for 4 hours. After standing overnight, the mixture is successively washed with dilute hydrochloric acid, water, a 5% aqueous potassium carbonate solution and finally water. The mixture is then dried over magnesium sulfate. Removal of the magnesium sulfate and solvent leaves the desired product as a yellow oil which readily crystallized on cooling. The crude product is recrystallized from ethanol to give 9.5 grams with m.p. 85°-88° C. the mixture is successively washed with dilute hydrochloric acid, water The mixture is then dried over magnesium sulfate Removal of the magnesium sulfate and solvent

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

Procedure: 2-Chlorosulphenylbenzoyl chloride (6 parts, 0.029M) dissolved in diethylether (30 ml) was added dropwise at 0 to 3° C. to a stirred solution of 1-methylbutylamine (7.36 parts, 0.84M ex Aldrich) in diethylether (30 ml). The reactants were stirred for 16 hours whilst allowing the temperature to rise to about 20° C. The ether solution was then screened, washed with water and dried over magnesium sulphate. After evaporation of the ether, the product was obtained as a pale yellow gum (5.5 parts, 86% theory) which gradually solidified on standing. This was recrystallised from hexane. mp=52-54° C. to rise to about 20° C washed with water dried over magnesium sulphate After evaporation of the ether the product was obtained as a pale yellow gum (5.5 parts, 86% theory) which This was recrystallised from hexane

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

Procedure: Following the general procedure of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[(2-methylbutyl)amino]methyl}-2-thienyl)-1H-indole-7-carboxamide, (5-formyl-2-thienyl)boronic acid (50 mg, 0.32 mmol), (1-methylbutyl)amine (29 mg, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 43 mg of crude (5-{[(1-methylbutyl)amino]methyl}-2-thienyl)boronic acid. The crude (5-{[(1-methylbutyl)amino]methyl}-2-thienyl)boronic acid was then reacted with 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (65 mg, 0.157 mmol), K2CO3 (130 mg, 0.942 mmol), and tetrakis(triphenylphosphine)palladium(0) (4 mg, 0.003 mmol) to give 35.2 mg of the title compound (60%). were reacted

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

Procedure: Following the general procedure of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-{[(2-methylbutyl)amino]methyl}-2-thienyl)-1H-indole-7-carboxamide, (5-formyl-2-thienyl)boronic acid (50 mg, 0.32 mmol), (1-methylbutyl)amine (29 mg, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 43 mg of crude (5-{[(1-methylbutyl)amino]methyl}-2-thienyl)boronic acid. The crude (5-{[(1-methylbutyl)amino]methyl}-2-thienyl)boronic acid was then reacted with 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (65 mg, 0.157 mmol), K2CO3 (130 mg, 0.942 mmol), and tetrakis(triphenylphosphine)palladium(0) (4 mg, 0.003 mmol) to give 35.2 mg of the title compound (60%). were reacted

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

Procedure: Following the procedure to make (13), 1-methylbutyl amine was substituted for butyl amine to give the title compound after purification. 1H NMR (500 MHz, DMSO-d6): δ 8.45 (s, 2H), 8.12 (s, 1H), 7.37 (d, 2H), 7.24 (t, 2H), 7.17 (t, 1H), 6.79 (d, 1H), 4.35 (s, 2H), 3.60 (d, 2H), 3.41 (m, 1H), 3.30 (water), 2.89 (d, 2H), 2.48 (DMSO), 1.62 (m, 2H), 1.55 (m, 2H), 1.34-1.19 (m, 6H), 0.96 (d, 3H), 0.80 (t, 3H), 0.62 (m, 4H).

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