2-(furan-2-ylmethylsulfanyl)ethanamine

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:70.01; pressure:0.00; stir:

Procedure: Dilution of the aliquot (2 uL) with DMSO (200 uL).

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

Procedure: A solution of silver nitrate (8.25 g) in dimethylformamide (50 ml) was added dropwise to a solution of N-cyano-N'-methylcarbamimidothioic acid, methyl ester (6.1 g), triethylamine (4.8 g) and 2-[[[2-furanyl]methyl]thio]ethanamine (7.8 g) in methanol (150 ml). After 42 hr at 50° the mixture was filtered and the filtrate evaporated. The residue was partitioned between ethyl acetate and water. The organic layers were dried and evaporated to give an oil which yielded crystalline N-cyano-N'-[2-[[[2-furanyl]methyl]thio]ethyl]-N"-methylguanidine (3.9 g) m.p. 78°-82°. After 42 hr at 50° the mixture was filtered the filtrate evaporated The residue was partitioned between ethyl acetate and water The organic layers were dried evaporated to give an oil which

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

Procedure: Prepared in a similar manner as described in example 4 from 4-methoxy-3-methylbenzoic acid and 2-(furan-2-ylmethylthio)ethanamine. Yield 58%. 1H NMR (500 MHz, CDCl3) 2.23 (s, 3H), 2.76 (t, 2H, J=6.37 Hz), 3.59 (q, 2H, J=12.2 Hz), 3.76 (s, 2H), 3.86 (s, 3H), 6.22 (dd, 1H, J=3.49 Hz, J=2.67 Hz), 6.30 (dd, 1H, J=3.04 Hz, J=1.78 Hz), 6.46 (m, 1H, broad), 6.83 (d, 1H, J=8.51 Hz), 7.34 (dd, 1H, J=1.97 Hz, J=1 Hz), 7.56 (d, 1H, J=1.72 Hz), 7.61 (dd, 1H, J=8.53 Hz, J=2.25 Hz). MS (M+H, 306). Prepared in a similar manner

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: 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 2-(furfurylthio)ethylamine of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 399 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.92 (1H, br. s.) 10.46 (1H, s) 8.29 (1H, t, J=5.71 Hz) 8.06 (1H, d, J=6.05 Hz) 7.84 (1H, d, J=5.37 Hz) 7.56 (1H, td, J=1.10, 0.54 Hz) 7.44 (1H, d, J=5.37 Hz) 7.38 (1H, dd, J=3.51, 1.76 Hz) 6.80 (1H, d, J=6.15 Hz) 6.57 (1H, d, J=3.32 Hz) 6.36 (1H, dd, J=3.17, 1.90 Hz) 6.28 (1H, dd, J=3.22, 0.59 Hz) 3.78 (2H, s) 3.36-3.44 (2H, m) 2.59 (2H, dd, J=7.96, 6.20 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 2-(furfurylthio)ethylamine of 1-BOC-3-aminopyrrolidine. LCMS (ESI) 399 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.92 (1H, br. s.) 10.46 (1H, s) 8.29 (1H, t, J=5.71 Hz) 8.06 (1H, d, J=6.05 Hz) 7.84 (1H, d, J=5.37 Hz) 7.56 (1H, td, J=1.10, 0.54 Hz) 7.44 (1H, d, J=5.37 Hz) 7.38 (1H, dd, J=3.51, 1.76 Hz) 6.80 (1H, d, J=6.15 Hz) 6.57 (1H, d, J=3.32 Hz) 6.36 (1H, dd, J=3.17, 1.90 Hz) 6.28 (1H, dd, J=3.22, 0.59 Hz) 3.78 (2H, s) 3.36-3.44 (2H, m) 2.59 (2H, dd, J=7.96, 6.20 Hz)

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

Procedure: A solution of silver nitrate (8.25 g) in dimethylformamide (50 ml) was added dropwise to a solution of N-cyano-N'-methylcarbamimidothioic acid, methyl ester (6.1 g), triethylamine (4.8 g) and 2-[[[2-furanyl]methyl]thio]ethanamine (7.8 g) in methanol (150 ml). After 42 hr at 50° the mixture was filtered and the filtrate evaporated. The residue was partitioned between ethyl acetate and water. The organic layers were dried and evaporated to give an oil which yielded crystalline N-cyano-N'-[2-[[[2-furanyl]methyl]thio]ethyl]-N"-methylguanidine (3.9 g) m.p. 78°-82°. After 42 hr at 50° the mixture was filtered the filtrate evaporated The residue was partitioned between ethyl acetate and water The organic layers were dried evaporated to give an oil which

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

Procedure: A solution of silver nitrate (8.25 g) in dimethylformamide (50 ml) was added dropwise to a solution of N-cyano-N'-methylcarbamimidothioic acid, methyl ester (6.1 g), triethylamine (4.8 g) and 2-[[[2-furanyl]methyl]thio]ethanamine (7.8 g) in methanol (150 ml). After 42 hr at 50° the mixture was filtered and the filtrate evaporated. The residue was partitioned between ethyl acetate and water. The organic layers were dried and evaporated to give an oil which yielded crystalline N-cyano-N'-[2-[[[2-furanyl]methyl]thio]ethyl]-N"-methylguanidine (3.9 g) m.p. 78°-82°. After 42 hr at 50° the mixture was filtered the filtrate evaporated The residue was partitioned between ethyl acetate and water The organic layers were dried evaporated to give an oil which