2-benzylsulfanylethanamine

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: 30 grams of ethyl nicotinate and 80 grams of 2-benzylthio ethylamine are heated for 12 hours at 170°-180° C. The ethane liberated during the reaction is removed by means of a Dean Stark apparatus. After cooling, the reaction mixture is dissolved in 400 cc of carbon tetrachloride; by addition of petroleum ether, the N-(2-benzylthioethyl)nicotinamide crystallizes: 47 g. By crystallization in a mixture of carbon tetrachloride and cyclohexane, there are recovered colorless crystals of the above product melting at 79° C. is removed by means of a Dean Stark apparatus After cooling the reaction mixture is dissolved in 400 cc of carbon tetrachloride by addition of petroleum ether the N-(2-benzylthioethyl)nicotinamide crystallizes By crystallization in a mixture of carbon tetrachloride and cyclohexane, there are recovered colorless crystals of the above product melting at 79° C.

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

Procedure: 30 grams of ethyl nicotinate and 80 grams of 2-benzylthio ethylamine are heated for 12 hours at 170°-180° C. The ethane liberated during the reaction is removed by means of a Dean Stark apparatus. After cooling, the reaction mixture is dissolved in 400 cc of carbon tetrachloride; by addition of petroleum ether, the N-(2-benzylthioethyl)nicotinamide crystallizes: 47 g. By crystallization in a mixture of carbon tetrachloride and cyclohexane, there are recovered colorless crystals of the above product melting at 79° C. is removed by means of a Dean Stark apparatus After cooling the reaction mixture is dissolved in 400 cc of carbon tetrachloride by addition of petroleum ether the N-(2-benzylthioethyl)nicotinamide crystallizes By crystallization in a mixture of carbon tetrachloride and cyclohexane, there are recovered colorless crystals of the above product melting at 79° C.

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

Procedure: This compound was prepared in an analogous manner as 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide using 2-(benzylsulfanyl)ethanamine instead of tert-butyl-2-amino ethyl carbamate. LCMS (ESI) 409 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (1H, br. s.) 10.33-10.38 (1H, m) 8.22 (1H, t, J=5.66 Hz) 8.00 (1H, d, J=5.47 Hz) 7.76 (1H, d, J=5.47 Hz) 7.45-7.51 (1H, m) 7.15-7.36 (5H, m) 6.82 (1H, d, J=5.47 Hz) 6.43 (1H, dd, J=3.42, 1.85 Hz) 3.75 (2H, s) 3.35-3.47 (2H, m) 2.51-2.58 (2H, m)

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

Procedure: This compound was prepared in an analogous manner as 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide using 2-(benzylsulfanyl)ethanamine instead of tert-butyl-2-amino ethyl carbamate. LCMS (ESI) 409 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (1H, br. s.) 10.33-10.38 (1H, m) 8.22 (1H, t, J=5.66 Hz) 8.00 (1H, d, J=5.47 Hz) 7.76 (1H, d, J=5.47 Hz) 7.45-7.51 (1H, m) 7.15-7.36 (5H, m) 6.82 (1H, d, J=5.47 Hz) 6.43 (1H, dd, J=3.42, 1.85 Hz) 3.75 (2H, s) 3.35-3.47 (2H, m) 2.51-2.58 (2H, m)

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

Procedure: To a suspension of 0.1 mole cysteamine hydrochloride in 20 mL methanol were added 13.6 mL of 25% ammonia solution, followed by dropwise addition of 0.12 mole benzyl bromide at room temperature. The mixture was stirred for 0.5 h, and the formed precipitate of S-dibenzylcysteamine was collected by filtration. The product was extracted with ether (3×100 mL) and the organic phase was successively washed with brine (2×100 mL), dried over MgSO4 and the solvent evaporated in vacuo. The crude product was essentially pure enough for the next step. It could, however be recrystallized from ethyl acetate. Yield 86%, of white solid. m.p. 85–6° C. NMR (CDCl3) in agreement with the title compound. the formed precipitate of S-dibenzylcysteamine was collected by filtration The product was extracted with ether (3×100 mL) the organic phase was successively washed with brine (2×100 mL) dried over MgSO4 the solvent evaporated in vacuo It could, however be recrystallized from ethyl acetate

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: To a suspension of 0.1 mole cysteamine hydrochloride in 20 mL methanol were added 13.6 mL of 25% ammonia solution, followed by dropwise addition of 0.12 mole benzyl bromide at room temperature. The mixture was stirred for 0.5 h, and the formed precipitate of S-dibenzylcysteamine was collected by filtration. The product was extracted with ether (3×100 mL) and the organic phase was successively washed with brine (2×100 mL), dried over MgSO4 and the solvent evaporated in vacuo. The crude product was essentially pure enough for the next step. It could, however be recrystallized from ethyl acetate. Yield 86%, of white solid. m.p. 85–6° C. NMR (CDCl3) in agreement with the title compound. the formed precipitate of S-dibenzylcysteamine was collected by filtration The product was extracted with ether (3×100 mL) the organic phase was successively washed with brine (2×100 mL) dried over MgSO4 the solvent evaporated in vacuo It could, however be recrystallized from ethyl acetate

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

Procedure: To a suspension of 0.1 mole cysteamine hydrochloride in 20 mL methanol were added 13.6 mL of 25% ammonia solution, followed by dropwise addition of 0.12 mole benzyl bromide at room temperature. The mixture was stirred for 0.5 h, and the formed precipitate of S-dibenzylcysteamine was collected by filtration. The product was extracted with ether (3×100 mL) and the organic phase was successively washed with brine (2×100 mL), dried over MgSO4 and the solvent evaporated in vacuo. The crude product was essentially pure enough for the next step. It could, however be recrystallized from ethyl acetate. Yield 86%, of white solid. m.p. 85–6° C. NMR (CDCl3) in agreement with the title compound. the formed precipitate of S-dibenzylcysteamine was collected by filtration The product was extracted with ether (3×100 mL) the organic phase was successively washed with brine (2×100 mL) dried over MgSO4 the solvent evaporated in vacuo It could, however be recrystallized from ethyl acetate