N'-methylpropane-1,3-diamine

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 5-benzoyl-2-nitrobenzaldehyde (0.0058 mol) in THF (100 ml) was hydrogenated with 10% Pd/C (1 g) as a catalyst in the presence of 4% thiophene solution (1 mL). After uptake of H2 (3 equiv), the mixture was put in an autoclave. N-cyclohexyl, N-methyl-propane-1,3-diamine (0.01 mol) and CaH2 (0.5 g) were added and the mixture was reacted under 10 atm of CO2 and 50 atm of H2 at 50° C. for 16 hours. When the reaction was complete, the mixture was purified over silica gel on a glass filter (eluent: 90:10 CH2Cl2:(CH3OH:NH3)). The product fractions were collected and the solvent was evaporated to yield the title compound as a residue. the mixture was purified over silica gel on a glass filter (eluent: 90:10 CH2Cl2:(CH3OH:NH3)) The product fractions were collected the solvent was evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 75.0 g (0.87 mol) of pivalaldehyde are added dropwise to a solution of 76.7 g (0.87 mol) of 3-methylaminopropylamine in 200 ml of dry cyclohexane. After the addition, the solution is heated under reflux in a water separator for 3 hours. The solvent is then removed in a rotary evaporator and the residue is distilled. Boiling point: 69° C./67 mbar After the addition the solution is heated The solvent is then removed in a rotary evaporator the residue is distilled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of toluene and 4,4 dipropylcyclohexane 1 carboxy 1 acetic acid anhydride (1 equivalent) was added 3 methylaminopropylamine (1.05 equivalents). The reaction mixture was heated at reflux using a Dean Stark trap. Following collection of water (1 equivalent), the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was used without further purification. The reaction mixture was heated at reflux concentrated under reduced pressure The residue was used without further purification

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of N-methyl-1,3-diaminopropane (37.6 mL, 312 mmol) and sulfamide (10.0 g, 104 mmol) were heated at reflux for 16 hr. The solvent was evaporated in vacuo and the residue was purified by chromatography (SiO2, EtOAc/CH2Cl2: 1:1) to afford the title compound as an oil. at reflux for 16 hr The solvent was evaporated in vacuo the residue was purified by chromatography (SiO2, EtOAc/CH2Cl2: 1:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of N-methyl-1,3-diaminopropane (37.6 mL, 312 mmol) and sulfamide (10.0 g, 104 mmol) were heated at reflux for 16 hr. The solvent was evaporated in vacuo and the residue was purified by chromatography (SiO2, EtOAc/CH2Cl2: 1:1) to afford the title compound as an oil. at reflux for 16 hr The solvent was evaporated in vacuo the residue was purified by chromatography (SiO2, EtOAc/CH2Cl2: 1:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl trifluoroacetate [383-63-1] (7.5 mL, 62.9 mmol) was slowly added to an ambient temperature solution of N1-methylpropane-1,3-diamine [6291-84-5] (6.5 mL, 62.8 mmol) in anhydrous THF (100 mL) then allowed to stir, under N2 blanket for 17 h. The reaction solution was then evaporated to provide 12.3 g of clear colorless liquid. LRMS (ESI) m/z 185.1 [(M+H)]+, calc'd for C6H11F3N2O: 184.16. The reaction solution was then evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl trifluoroacetate [383-63-1] (7.5 mL, 62.9 mmol) was slowly added to an ambient temperature solution of N1-methylpropane-1,3-diamine [6291-84-5] (6.5 mL, 62.8 mmol) in anhydrous THF (100 mL) then allowed to stir, under N2 blanket for 17 h. The reaction solution was then evaporated to provide 12.3 g of clear colorless liquid. LRMS (ESI) m/z 185.1 [(M+H)]+, calc'd for C6H11F3N2O: 184.16. The reaction solution was then evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared from [4-carbamoyl-3-(2,3,6-trifluoro-4-methyl-benzyloxy)-isothiazol-5-yl]-carbamic acid phenyl ester and N-methyl-propane-1,3-diamine by the procedure analogous to Example 1. MS (APCl, m/z): 432 [M+H]+.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared from [4-carbamoyl-3-(2,3,6-trifluoro-4-methyl-benzyloxy)-isothiazol-5-yl]-carbamic acid phenyl ester and N-methyl-propane-1,3-diamine by the procedure analogous to Example 1. MS (APCl, m/z): 432 [M+H]+.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared from [4-carbamoyl-3-(2,3,6-trifluoro-4-methyl-benzyloxy)-isothiazol-5-yl]-carbamic acid phenyl ester and N-methyl-propane-1,3-diamine by the procedure analogous to Example 1. MS (APCl, m/z): 432 [M+H]+.

反応条件: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-Methyl-1,3-diaminopropane (50 g, 0.56 mol) was dissolved in 200 mL acetonitrile followed by addition of ethyl trifluoroacetate (154 ml, 1.28 mol). The reaction mixture was stirred overnight at 85° C. The solvent was then removed in vacuo to yield the depicted product as a brown oil (101 g, 98.5%). The solvent was then removed in vacuo