2-[di(propan-2-yl)amino]ethanol

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

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

Procedure: 1-(Benzo[d][1,3]dioxol-5-yl)-N-(5-((2-(diisopropylamino)ethoxy)(2-methoxyphenyl)methyl)pyridin-2-yl)cyclopropanecarboxamide was prepared from 1-(benzo[d][1,3]dioxol-5-yl)-N-(5-(hydroxy(2-methoxyphenyl)methyl)pyridin-2-yl)cyclopropanecarboxamide and 2-(diisopropylamino)ethanol in a manner analogous to that of 1-(benzo[d][1,3]dioxol-5-yl)-N-(5-((3-hydroxypropoxy)(2-methoxyphenyl)methyl)pyridin-2-yl)cyclopropanecarboxamide.

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

Procedure: Treatment of 4-benzyloxy-5,7-dichloroquinoline-2-carboxylic acid (1 g, Example 33b) with thionyl chloride (10 ml) followed by 2-(diisopropylamino)ethanol (1.63 ml) as described in Example 33c gave 2-diisopropylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.85 g). δ (360 MHz, DMSO-d6) 0.98 (12H, 2d, CH3), 2.77 (2H, t, CH2N), 3.01 (2H, m, C-H), 4.27 (2H, t, CO2CH2), 5.49 (2H, s, OCH2), 7.38 (1H, d, p-ArH), 7.44 (2H, t, m-ArH), 7.58 (2H, d, o-ArH), 7.72 (1H, s, 3-H), 7.81 (1H, d, 6-H) and 8.21 (1H, d, 8-H).

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 27.6 g (190 mmole) of 2-(diisopropylamino)ethanol, 6.83 g (81 mmole) of sodium bicarbonate, and 1.3 mL (70 mmole) of deionized water at room temperature was added 5.0 g (27 mmole) of cyanuric chloride. The temperature of the solution was raised to 30° C. and stirred for 1 hour at which time the evolution of carbon dioxide ceased. The temperature of the solution was raised to 45° C. and stirring was continued overnight. After cooling, the mixture was filtered, and the solids rinsed with methylene chloride. The combined filtrates were concentrated in vacuo to 6 g of 2-chloro-4,6-di-(2-(diisopropylamino)ethoxy)-1,3,5-triazine as a liquid. The temperature of the solution was raised to 45° C. After cooling the mixture was filtered the solids rinsed with methylene chloride The combined filtrates were concentrated in vacuo to 6 g of 2-chloro-4,6-di-(2-(diisopropylamino)ethoxy)-1,3,5-triazine as a liquid

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 27.6 g (190 mmole) of 2-(diisopropylamino)ethanol, 6.83 g (81 mmole) of sodium bicarbonate, and 1.3 mL (70 mmole) of deionized water at room temperature was added 5.0 g (27 mmole) of cyanuric chloride. The temperature of the solution was raised to 30° C. and stirred for 1 hour at which time the evolution of carbon dioxide ceased. The temperature of the solution was raised to 45° C. and stirring was continued overnight. After cooling, the mixture was filtered, and the solids rinsed with methylene chloride. The combined filtrates were concentrated in vacuo to 6 g of 2-chloro-4,6-di-(2-(diisopropylamino)ethoxy)-1,3,5-triazine as a liquid. The temperature of the solution was raised to 45° C. After cooling the mixture was filtered the solids rinsed with methylene chloride The combined filtrates were concentrated in vacuo to 6 g of 2-chloro-4,6-di-(2-(diisopropylamino)ethoxy)-1,3,5-triazine as a liquid

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

Procedure: 1-(Benzo[d][1,3]dioxol-5-yl)-N-(5-((2-(diisopropylamino)ethoxy)(2-methoxyphenyl)methyl)pyridin-2-yl)cyclopropanecarboxamide was prepared from 1-(benzo[d][1,3]dioxol-5-yl)-N-(5-(hydroxy(2-methoxyphenyl)methyl)pyridin-2-yl)cyclopropanecarboxamide and 2-(diisopropylamino)ethanol in a manner analogous to that of 1-(benzo[d][1,3]dioxol-5-yl)-N-(5-((3-hydroxypropoxy)(2-methoxyphenyl)methyl)pyridin-2-yl)cyclopropanecarboxamide.

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

Procedure: Treatment of 4-benzyloxy-5,7-dichloroquinoline-2-carboxylic acid (1 g, Example 33b) with thionyl chloride (10 ml) followed by 2-(diisopropylamino)ethanol (1.63 ml) as described in Example 33c gave 2-diisopropylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.85 g). δ (360 MHz, DMSO-d6) 0.98 (12H, 2d, CH3), 2.77 (2H, t, CH2N), 3.01 (2H, m, C-H), 4.27 (2H, t, CO2CH2), 5.49 (2H, s, OCH2), 7.38 (1H, d, p-ArH), 7.44 (2H, t, m-ArH), 7.58 (2H, d, o-ArH), 7.72 (1H, s, 3-H), 7.81 (1H, d, 6-H) and 8.21 (1H, d, 8-H).

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

Procedure: Treatment of 4-benzyloxy-5,7-dichloroquinoline-2-carboxylic acid (1 g, Example 33b) with thionyl chloride (10 ml) followed by 2-(diisopropylamino)ethanol (1.63 ml) as described in Example 33c gave 2-diisopropylaminoethyl 4-benzyloxy-5,7-dichloroquinoline-2-carboxylate (0.85 g). δ (360 MHz, DMSO-d6) 0.98 (12H, 2d, CH3), 2.77 (2H, t, CH2N), 3.01 (2H, m, C-H), 4.27 (2H, t, CO2CH2), 5.49 (2H, s, OCH2), 7.38 (1H, d, p-ArH), 7.44 (2H, t, m-ArH), 7.58 (2H, d, o-ArH), 7.72 (1H, s, 3-H), 7.81 (1H, d, 6-H) and 8.21 (1H, d, 8-H).

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 27.6 g (190 mmole) of 2-(diisopropylamino)ethanol, 6.83 g (81 mmole) of sodium bicarbonate, and 1.3 mL (70 mmole) of deionized water at room temperature was added 5.0 g (27 mmole) of cyanuric chloride. The temperature of the solution was raised to 30° C. and stirred for 1 hour at which time the evolution of carbon dioxide ceased. The temperature of the solution was raised to 45° C. and stirring was continued overnight. After cooling, the mixture was filtered, and the solids rinsed with methylene chloride. The combined filtrates were concentrated in vacuo to 6 g of 2-chloro-4,6-di-(2-(diisopropylamino)ethoxy)-1,3,5-triazine as a liquid. The temperature of the solution was raised to 45° C. After cooling the mixture was filtered the solids rinsed with methylene chloride The combined filtrates were concentrated in vacuo to 6 g of 2-chloro-4,6-di-(2-(diisopropylamino)ethoxy)-1,3,5-triazine as a liquid

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

Procedure: 2-Diisopropylaminoethyl Tributylstannyl Ether is prepared from 89.4 gm (0.15 mole) bis(tributyltin) oxide and 43.5 gm (0.30 mole) 2-diisopropylaminoethanol in 200 ml benzene. This is stirred and heated to reflux in a system that contains a Dean-Starke tube. After refluxing for 23 hours a total of 2.6 ml of water (theory 2.7 ml) had collected in the Dean-Starke tube. Solvent is stripped off on a rotating evaporator to provide 134.3 gm of orange liquid. This is fractionated at reduced pressure with collection at 147°-155° C. at 0.4 mm of 87.6 gm of straw liquid (Percent theory - 73). Infrared spectral analysis shows this liquid to be the desired ether. heated to reflux in a system that had collected in the Dean-Starke tube Solvent is stripped off on a rotating evaporator

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

Procedure: 1-(Benzo[d][1,3]dioxol-5-yl)-N-(5-((2-(diisopropylamino)ethoxy)(2-methoxyphenyl)methyl)pyridin-2-yl)cyclopropanecarboxamide was prepared from 1-(benzo[d][1,3]dioxol-5-yl)-N-(5-(hydroxy(2-methoxyphenyl)methyl)pyridin-2-yl)cyclopropanecarboxamide and 2-(diisopropylamino)ethanol in a manner analogous to that of 1-(benzo[d][1,3]dioxol-5-yl)-N-(5-(3-hydroxypropoxy)(2-methoxyphenyl)methyl)pyridin-2-yl)cyclopropanecarboxamide.

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

Procedure: 2-Diisopropylaminoethyl Tributylstannyl Ether is prepared from 89.4 gm (0.15 mole) bis(tributyltin) oxide and 43.5 gm (0.30 mole) 2-diisopropylaminoethanol in 200 ml benzene. This is stirred and heated to reflux in a system that contains a Dean-Starke tube. After refluxing for 23 hours a total of 2.6 ml of water (theory 2.7 ml) had collected in the Dean-Starke tube. Solvent is stripped off on a rotating evaporator to provide 134.3 gm of orange liquid. This is fractionated at reduced pressure with collection at 147°-155° C. at 0.4 mm of 87.6 gm of straw liquid (Percent theory - 73). Infrared spectral analysis shows this liquid to be the desired ether. heated to reflux in a system that had collected in the Dean-Starke tube Solvent is stripped off on a rotating evaporator