tert-butyl N-[(3-aminophenyl)methyl]carbamate

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: A mixture of 102.1 g (600 mmol) of 3,3-bis-methylmercapto-2-cyano-acrylonitrile, 133.3 g (600 mmol) of 3-(N-Boc-aminomethyl)-aniline (WO 93/00095) and 1100 ml of methanol is heated under reflux for 6.5 hours and then concentrated by evaporation in vacuo. Crystallization of the residue from ethyl acetate, filtration and washing the filtration residue with ethyl acetate yield 3-[3-(N-Boc-aminomethyl)-phenylamino]-2-cyano-3-methylmercapto-acrylonitrile; m.p. 150-151° C. is heated under reflux for 6.5 hours concentrated by evaporation in vacuo Crystallization of the residue from ethyl acetate, filtration washing the filtration residue with ethyl acetate

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

Procedure: A mixture of 102.1 g (600 mmol) of 3,3-bis-methylmercapto-2-cyano-acrylonitrile, 133.3 g (600 mmol) of 3-(N-Boc-aminomethyl)-aniline (WO 93/00095) and 1100 ml of methanol is heated under reflux for 6.5 hours and then concentrated by evaporation in vacuo. Crystallization of the residue from ethyl acetate, filtration and washing the filtration residue with ethyl acetate yield 3-[3-(N-Boc-aminomethyl)-phenylamino]-2-cyano-3-methylmercapto-acrylonitrile; m.p. 150-151° C. is heated under reflux for 6.5 hours concentrated by evaporation in vacuo Crystallization of the residue from ethyl acetate, filtration washing the filtration residue with ethyl acetate

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

Procedure: To a solution of N-(t-butyloxycarbonyl)-3-nitrobenzylamine (13.8 g, 54.7 mmol) in dimethylformamide (200 mL) was added tin(II) chloride dihydrate (74.1 g, 328 mmol) and the reaction was stirred at room temperature for 48 hours. The dimethylformamide was removed under vacuum. The residue was resuspended in dichloromethane (300 ml), washed with brine (200 mL), filtered through a celite pad, and the solvent removed to provide 12.2 g of the title compound. (100%). The dimethylformamide was removed under vacuum washed with brine (200 mL) filtered through a celite pad the solvent removed

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

Procedure: N-{3-[(t-Butoxycarbonylamino)methyl]phenyl}2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide was prepared from 2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1 ′-biphenyl-4-carboxylic acid and 3-[(t-butoxycarbonylamino)-methyl]aniline using method J. NMR; δH [2H6]—DMSO 10.34,(1H, b), 8.06,(2H, d), 7.91,(1H, dd), 7.79,(1H, d), 7.70,(1H, s), 7.66,(1H, d), 7.59-7.56,(3H, m), 7.41,(1H, t), 7.29,(1H, t), 6.98,(1H, d), 4.14,(2H, d), 2.57,(3H, s), 2.34,(3H, s), 1.40,(9H, s). LCMS; retention time 3.59 min, [M-H]− 497.

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

Procedure: Prepared analogously to Example 9 from 1-benzoyl-3-(1-chloro-1-phenyl-methylidene)-2-indolinone and 3-tert.butoxycarbonylaminomethyl-aniline in triethylamine.

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: N-{3-[(t-Butoxycarbonylamino)methyl]phenyl}2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide was prepared from 2′-methyl-5′-(5-methyl-1,3,4-oxadiazol-2-yl)-1,1 ′-biphenyl-4-carboxylic acid and 3-[(t-butoxycarbonylamino)-methyl]aniline using method J. NMR; δH [2H6]—DMSO 10.34,(1H, b), 8.06,(2H, d), 7.91,(1H, dd), 7.79,(1H, d), 7.70,(1H, s), 7.66,(1H, d), 7.59-7.56,(3H, m), 7.41,(1H, t), 7.29,(1H, t), 6.98,(1H, d), 4.14,(2H, d), 2.57,(3H, s), 2.34,(3H, s), 1.40,(9H, s). LCMS; retention time 3.59 min, [M-H]− 497.