QUINAPRIL RELATED COMPOUND A (50 MG) (ETHYL[3S-[2(R*),3A,11A BETA]]-1,3,4,6,11,11A-HEXAHYDRO-3-METHYL-1,4-DIOXO-ALPHA-(2-PHENY-LETHYL)-2H-PYRAZINO[1,2-B]ISOQUINOLINE-2-ACETATE)

Base Information

• Chemical Name: QUINAPRIL RELATED COMPOUND A (50 MG) (ETHYL[3S-[2(R*),3A,11A BETA]]-1,3,4,6,11,11A-HEXAHYDRO-3-METHYL-1,4-DIOXO-ALPHA-(2-PHENY-LETHYL)-2H-PYRAZINO[1,2-B]ISOQUINOLINE-2-ACETATE)
• CAS No.: 103733-49-9
• Molecular Formula: C25H28 N2 O4
• Molecular Weight: 420.508
• Hs Code.: 2933997500
• Mol file: 103733-49-9.mol

Synonyms:2H-Pyrazino[1,2-b]isoquinoline-2-aceticacid, 1,3,4,6,11,11a-hexahydro-3-methyl-1,4-dioxo-a-(2-phenylethyl)-, ethyl ester, [3S-[2(R*),3a,11ab]]-; PD 109488

Chemical Property of QUINAPRIL RELATED COMPOUND A (50 MG) (ETHYL[3S-[2(R*),3A,11A BETA]]-1,3,4,6,11,11A-HEXAHYDRO-3-METHYL-1,4-DIOXO-ALPHA-(2-PHENY-LETHYL)-2H-PYRAZINO[1,2-B]ISOQUINOLINE-2-ACETATE)

Chemical Property:

• Vapor Pressure: 1.68E-16mmHg at 25°C
• Boiling Point: 644.5°C at 760 mmHg
• PKA: -1.13±0.40(Predicted)
• Flash Point: 343.6°C
• PSA: 66.92000
• Density: 1.25g/cm³
• LogP: 2.61090

Purity/Quality:

98%Min ^*data from raw suppliers

QuinaprilDiketopiperazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Quinapril derivative. ACE inhibitor Quinapril Diketopiperazine (Quinapril EP Impurity D) is a Quinapril derivative. ACE inhibitor.

Technology Process of QUINAPRIL RELATED COMPOUND A (50 MG) (ETHYL[3S-[2(R*),3A,11A BETA]]-1,3,4,6,11,11A-HEXAHYDRO-3-METHYL-1,4-DIOXO-ALPHA-(2-PHENY-LETHYL)-2H-PYRAZINO[1,2-B]ISOQUINOLINE-2-ACETATE)

There total 6 articles about QUINAPRIL RELATED COMPOUND A (50 MG) (ETHYL[3S-[2(R*),3A,11A BETA]]-1,3,4,6,11,11A-HEXAHYDRO-3-METHYL-1,4-DIOXO-ALPHA-(2-PHENY-LETHYL)-2H-PYRAZINO[1,2-B]ISOQUINOLINE-2-ACETATE) 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: 80.0%

quinapril (85441-61-8,82768-84-1) → <3S-<2(R*),3α,11aβ>>-1,3,4,6,11,11a-hexahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)-2H-pyrazino<1,2-b>isoquinoline-2-acetic acid, ethyl ester (103733-49-9)

Guidance literature:

With acetic acid; In toluene; at 95 ℃; for 0.5h;

DOI:10.1021/jm00160a026

Reference yield:

quinapril hydrochloride (82586-55-8) → quinapril (85441-61-8,82768-84-1) + <3S-<2(R*),3α,11aβ>>-1,3,4,6,11,11a-hexahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)-2H-pyrazino<1,2-b>isoquinoline-2-acetic acid, ethyl ester (103733-49-9)

Guidance literature:

With citric acid; at 80 ℃; pH=2.60; Further Variations:; pH-values; Kinetics;

DOI:10.1023/A:1013695030082

Reference yield:

(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1,1-dimethylethyl ester (77497-74-6,189094-06-2,82716-91-4) → <3S-<2(R*),3α,11aβ>>-1,3,4,6,11,11a-hexahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)-2H-pyrazino<1,2-b>isoquinoline-2-acetic acid, ethyl ester (103733-49-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / Et₃N, DCC, 1-hydroxybenzotriazole / tetrahydrofuran / Ambient temperature

2: TFA / 1 h / Ambient temperature

3: 80 percent / AcOH / toluene / 0.5 h / 95 °C

With benzotriazol-1-ol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; toluene;

DOI:10.1021/jm00160a026

upstream raw materials:

quinapril

quinapril hydrochloride

L-Tic-OH

(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1,1-dimethylethyl ester

Refernces

• 1、 Klutchko,Blankley,Fleming,Hinkley,Werner,Nordin,Holmes,Hoefle,Cohen,Essenburg. "Synthesis of novel angiotensin converting enzyme inhibitor quinapril and related compounds. A divergence of structure-activity relationships for non-sulfhydryl and sulfhydryl types". . p. 1953 - 1961. Retrieved 2007/10/02.