dicyclopropylmethanamine

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: 9.2 g of β-chloroethyl isothiocyanate dissolved in 20 ml tetrahydrofuran are added dropwise to a solution of 9 g of dicyclopropylmethylamine in 70 ml tetrahydrofuran. The reaction mixture is kept at a temperature of from 0° to +5° C. during the addition, then maintained at room temperature for 2 hours. The solvent is evaporated to dryness and the residue, consisting essentially of N-(1,1-dicyclopropylmethyl) N'-(β-chloroethyl) thiourea, is recovered and used without any further purification for the next step of the synthesis. The reaction mixture is kept at a temperature of from 0° to +5° C. during the addition The solvent is evaporated to dryness is recovered used without any further purification for the next step of the synthesis

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

Procedure: A solution made from 13.4 g of dicyclopropylmethylamine in 30 ml tetrahydrofuran is added dropwise to a solution of 13 g of β-chloroetyl isocyanate in 15 ml tetrahydrofuran while maintaining the inner temperature from 0° to +5° C. Then, the reaction mixture is kept at room temperature for 15 hours. Afterwards, the solution is evaporated to dryness and the dry residue, weighing 26.5 g, is used as such for the next step of the synthesis. For analytical purpose, a sample of the raw urea is recrystallised from acetonitrile. The N-(dicyclopropylmethyl) N-(β-chloroethyl) urea occurs as white crystals melting at 103°-104° C. with decomposition. while maintaining the inner temperature from 0° to +5° C Afterwards, the solution is evaporated to dryness such for the next step of the synthesis For analytical purpose, a sample of the raw urea is recrystallised from acetonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred slurry of 1,7-dichloro-5H-pyrido[4,3-b]indole-4-carbonitrile (16 g, 61 mmol) in dioxane (122 mL) was added dicyclopropylmethanamine (17 g, 153 mmol). The reaction mixture was heated to 135° C. for 1 d, cooled to room temperature, and concentrated. The residue was diluted with EtOAc and water. The aqueous layer was extracted with EtOAc (×3). The combined organics were washed with brine, dried (sodium sulfate), concentrated, and purified by flash chromatography to give the title compound. LRMS (APCI) calc'd for (C19H17ClN4) [M+H]+, 337.1. found 337.1. cooled to room temperature concentrated The residue was diluted with EtOAc and water The aqueous layer was extracted with EtOAc (×3) The combined organics were washed with brine dried (sodium sulfate) concentrated purified by flash chromatography

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

Procedure: N-Dicyclopropylmethyl-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 dicyclopropylmethylamine using method I.

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

Procedure: 9.2 g of β-chloroethyl isothiocyanate dissolved in 20 ml tetrahydrofuran are added dropwise to a solution of 9 g of dicyclopropylmethylamine in 70 ml tetrahydrofuran. The reaction mixture is kept at a temperature of from 0° to +5° C. during the addition, then maintained at room temperature for 2 hours. The solvent is evaporated to dryness and the residue, consisting essentially of N-(1,1-dicyclopropylmethyl) N'-(β-chloroethyl) thiourea, is recovered and used without any further purification for the next step of the synthesis. The reaction mixture is kept at a temperature of from 0° to +5° C. during the addition The solvent is evaporated to dryness is recovered used without any further purification for the next step of the synthesis

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

Procedure: A solution made from 13.4 g of dicyclopropylmethylamine in 30 ml tetrahydrofuran is added dropwise to a solution of 13 g of β-chloroetyl isocyanate in 15 ml tetrahydrofuran while maintaining the inner temperature from 0° to +5° C. Then, the reaction mixture is kept at room temperature for 15 hours. Afterwards, the solution is evaporated to dryness and the dry residue, weighing 26.5 g, is used as such for the next step of the synthesis. For analytical purpose, a sample of the raw urea is recrystallised from acetonitrile. The N-(dicyclopropylmethyl) N-(β-chloroethyl) urea occurs as white crystals melting at 103°-104° C. with decomposition. while maintaining the inner temperature from 0° to +5° C Afterwards, the solution is evaporated to dryness such for the next step of the synthesis For analytical purpose, a sample of the raw urea is recrystallised from acetonitrile