2(1H)-Isoquinolinecarboxylic acid, 7-[[4-(ethoxycarbonyl)-1-(4-pyridinyl)-4-piperidinyl]methoxy]-3,4-dihydro- , phenylmethyl ester

Base Information

• Chemical Name: 2(1H)-Isoquinolinecarboxylic acid, 7-[[4-(ethoxycarbonyl)-1-(4-pyridinyl)-4-piperidinyl]methoxy]-3,4-dihydro- , phenylmethyl ester
• CAS No.: 832088-74-1
• Molecular Formula: C31H35N3O5
• Molecular Weight: 529.636
• Mol file: 832088-74-1.mol

Synonyms:

Chemical Property of 2(1H)-Isoquinolinecarboxylic acid, 7-[[4-(ethoxycarbonyl)-1-(4-pyridinyl)-4-piperidinyl]methoxy]-3,4-dihydro- , phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2(1H)-Isoquinolinecarboxylic acid, 7-[[4-(ethoxycarbonyl)-1-(4-pyridinyl)-4-piperidinyl]methoxy]-3,4-dihydro- , phenylmethyl ester

There total 6 articles about 2(1H)-Isoquinolinecarboxylic acid, 7-[[4-(ethoxycarbonyl)-1-(4-pyridinyl)-4-piperidinyl]methoxy]-3,4-dihydro- , phenylmethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester (121912-29-6) + 7-chloromethoxy-3,4-dihydro-1H-isoquinolin-2-carboxylate benzyl ester (247132-42-9) → benzyl 7-[4-ethoxycarbonyl-1-(pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinolin-2-carboxylate (832088-74-1)

Guidance literature:

1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at 20 ℃; for 5.5h;

7-chloromethoxy-3,4-dihydro-1H-isoquinolin-2-carboxylate benzyl ester; In tetrahydrofuran; at -70 - 20 ℃;

DOI:10.1021/jm058160e

Reference yield:

7-methoxyisoquinoline (39989-39-4) → benzyl 7-[4-ethoxycarbonyl-1-(pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinolin-2-carboxylate (832088-74-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: H₂; AcOH / PtO₂ / 3 h / 2280 Torr

2.1: aq. HBr / 3 h / Heating

3.1: aq. NaOH / tetrahydrofuran / 20 °C

4.1: NaH / dimethylformamide / 0.5 h / 0 °C

4.2: 89 percent / dimethylformamide / 12 h / 20 °C

5.1: SO₂Cl₂ / CH₂Cl₂ / 1 h / 0 °C

6.1: LDA / tetrahydrofuran / 5.5 h / 20 °C

6.2: 92 percent / tetrahydrofuran / -70 - 20 °C

With sodium hydroxide; sulfuryl dichloride; hydrogen bromide; hydrogen; sodium hydride; acetic acid; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm058160e

Reference yield:

7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid benzyl ester (247132-40-7) → benzyl 7-[4-ethoxycarbonyl-1-(pyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinolin-2-carboxylate (832088-74-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 89 percent / dimethylformamide / 12 h / 20 °C

2.1: SO₂Cl₂ / CH₂Cl₂ / 1 h / 0 °C

3.1: LDA / tetrahydrofuran / 5.5 h / 20 °C

3.2: 92 percent / tetrahydrofuran / -70 - 20 °C

With sulfuryl dichloride; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm058160e

upstream raw materials:

1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester

7-chloromethoxy-3,4-dihydro-1H-isoquinolin-2-carboxylate benzyl ester

7-methoxyisoquinoline

7-methoxy-1,2,3,4-tetrahydroisoquinoline

Refernces

• 1、 Ueno, Hiroshi,Yokota, Katsuyuki,Hoshi, Jun-Ichi,Yasue, Katsutaka,Hayashi, Mikio,Uchida, Itsuo,Aisaka, Kazuo,Hase, Yasunori,Katoh, Susumu,Cho, Hidetsura. "Discovery of novel tetrahydroisoquinoline derivatives as potent and selective factor Xa inhibitors". . p. 185 - 189. Retrieved 2007/10/03.