N-(4-aminobutyl)acetamide

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

Procedure: To 8.0 g of 3,4-dihydro-3-(2-chlorophenyl)-6-chlorosulfonyl-2-methyl-4-oxothieno[2,3-d]pyrimidine were added 150 ml of dichloromethane, 3.3 g of 4-acetylaminobutylamine and 5.9 ml of triethylamine, and the mixture was stirred at room temperature for 3 hours. After the reaction mixture was washed with water, the concentrated residue was purified by means of silica gel chromatography to obtain 5.71 g of oily substance, which was crystallized from ethyl acetate-hexane to afford 4.44 g of the title compound, m.p. 203°-206° C. (decomposition). After the reaction mixture was washed with water the concentrated residue was purified by means of silica gel chromatography to obtain 5.71 g of oily substance, which was crystallized from ethyl acetate-hexane

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

Procedure: This compound was prepared in an analogous manner as 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester using N-(4-aminobutyl)acetamide instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 372 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (1H, br. s.) 10.36 (1H, s) 8.11 (1H, t, J=5.56 Hz) 8.02 (1H, d, J=5.47 Hz) 7.77 (2H, d, J=5.47 Hz) 7.48 (1H, d, J=5.47 Hz) 7.31 (1H, dd, J=3.51, 2.54 Hz) 6.82 (1H, d, J=5.47 Hz) 6.43 (1H, dd, J=3.51, 1.95 Hz) 3.19-3.27 (2H, m) 2.96-3.07 (2H, m) 1.77 (3H, s) 1.44-1.59 (2H, m) 1.39 (2H, dd, J=8.40, 6.83 Hz)

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

Procedure: This compound was prepared in an analogous manner as 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester using N-(4-aminobutyl)acetamide instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 372 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (1H, br. s.) 10.36 (1H, s) 8.11 (1H, t, J=5.56 Hz) 8.02 (1H, d, J=5.47 Hz) 7.77 (2H, d, J=5.47 Hz) 7.48 (1H, d, J=5.47 Hz) 7.31 (1H, dd, J=3.51, 2.54 Hz) 6.82 (1H, d, J=5.47 Hz) 6.43 (1H, dd, J=3.51, 1.95 Hz) 3.19-3.27 (2H, m) 2.96-3.07 (2H, m) 1.77 (3H, s) 1.44-1.59 (2H, m) 1.39 (2H, dd, J=8.40, 6.83 Hz)

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

Procedure: To 8.0 g of 3,4-dihydro-3-(2-chlorophenyl)-6-chlorosulfonyl-2-methyl-4-oxothieno[2,3-d]pyrimidine were added 150 ml of dichloromethane, 3.3 g of 4-acetylaminobutylamine and 5.9 ml of triethylamine, and the mixture was stirred at room temperature for 3 hours. After the reaction mixture was washed with water, the concentrated residue was purified by means of silica gel chromatography to obtain 5.71 g of oily substance, which was crystallized from ethyl acetate-hexane to afford 4.44 g of the title compound, m.p. 203°-206° C. (decomposition). After the reaction mixture was washed with water the concentrated residue was purified by means of silica gel chromatography to obtain 5.71 g of oily substance, which was crystallized from ethyl acetate-hexane

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

Procedure: This compound was prepared in an analogous manner as 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester using N-(4-aminobutyl)acetamide instead of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 372 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.52 (1H, br. s.) 10.36 (1H, s) 8.11 (1H, t, J=5.56 Hz) 8.02 (1H, d, J=5.47 Hz) 7.77 (2H, d, J=5.47 Hz) 7.48 (1H, d, J=5.47 Hz) 7.31 (1H, dd, J=3.51, 2.54 Hz) 6.82 (1H, d, J=5.47 Hz) 6.43 (1H, dd, J=3.51, 1.95 Hz) 3.19-3.27 (2H, m) 2.96-3.07 (2H, m) 1.77 (3H, s) 1.44-1.59 (2H, m) 1.39 (2H, dd, J=8.40, 6.83 Hz)