2(1H)-Isoquinolinecarboxylic acid, 3-[[[(1R)-1-[(4-chlorophenyl)methyl]-2-[4-(2-formylphenyl)-1-piperazinyl]- 2-oxoethyl]amino]carbonyl]-3,4-dihydro-, 1,1-dimethylethyl ester, (3R)-

Base Information

• Chemical Name: 2(1H)-Isoquinolinecarboxylic acid, 3-[[[(1R)-1-[(4-chlorophenyl)methyl]-2-[4-(2-formylphenyl)-1-piperazinyl]- 2-oxoethyl]amino]carbonyl]-3,4-dihydro-, 1,1-dimethylethyl ester, (3R)-
• CAS No.: 748808-82-4
• Molecular Formula: C35H39ClN4O5
• Molecular Weight: 631.171
• Mol file: 748808-82-4.mol

Synonyms:

Chemical Property of 2(1H)-Isoquinolinecarboxylic acid, 3-[[[(1R)-1-[(4-chlorophenyl)methyl]-2-[4-(2-formylphenyl)-1-piperazinyl]- 2-oxoethyl]amino]carbonyl]-3,4-dihydro-, 1,1-dimethylethyl ester, (3R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2(1H)-Isoquinolinecarboxylic acid, 3-[[[(1R)-1-[(4-chlorophenyl)methyl]-2-[4-(2-formylphenyl)-1-piperazinyl]- 2-oxoethyl]amino]carbonyl]-3,4-dihydro-, 1,1-dimethylethyl ester, (3R)-

There total 2 articles about 2(1H)-Isoquinolinecarboxylic acid, 3-[[[(1R)-1-[(4-chlorophenyl)methyl]-2-[4-(2-formylphenyl)-1-piperazinyl]- 2-oxoethyl]amino]carbonyl]-3,4-dihydro-, 1,1-dimethylethyl ester, (3R)- 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: 90.0%

2-(Piperazin-1-yl)benzaldehyde (736991-52-9) + (N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanine (252008-71-2) → 4-{(2R)-[(3R)-1,2,3,4-tetrahydroisoquinolinylcarboxamido]-3-(4-chlorophenyl)propionyl}-1-[2-formylphenyl]piperazine (748808-82-4)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine;

DOI:10.1016/j.bmcl.2004.06.059

Reference yield:

2-Fluorobenzaldehyde (446-52-6) → 4-{(2R)-[(3R)-1,2,3,4-tetrahydroisoquinolinylcarboxamido]-3-(4-chlorophenyl)propionyl}-1-[2-formylphenyl]piperazine (748808-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / potassium carbonate / dimethylformamide / 8 h / 150 °C

2: trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

3: 415 mg / diisopropylethylamine; HBTU / dimethylformamide / 6 h / 40 °C

With potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm049278i

Reference yield: 33.0%

trifluoroacetic acid (76-05-1) + 4-{(2R)-[(3R)-1,2,3,4-tetrahydroisoquinolinylcarboxamido]-3-(4-chlorophenyl)propionyl}-1-[2-formylphenyl]piperazine (748808-82-4) → 4-{(2R)-[(3R)-1,2,3,4-tetrahydroisoquinolinylcarboxamido]-3-(4-chlorophenyl)propionyl}-1-[2-(aminomethyl)phenyl]piperazine trifluoroacetate

Guidance literature:

4-{(2R)-[(3R)-1,2,3,4-tetrahydroisoquinolinylcarboxamido]-3-(4-chlorophenyl)propionyl}-1-[2-formylphenyl]piperazine; With ammonia; In methanol; for 24h;

With sodium tetrahydroborate; In methanol;

trifluoroacetic acid; In dichloromethane; for 0.25h;

DOI:10.1021/jm049278i

upstream raw materials:

2-(Piperazin-1-yl)benzaldehyde

(N-tert-butoxycarbonyl-D-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-4-chloro-D-phenylalanine

2-Fluorobenzaldehyde

Refernces

• 1、 Chen, Chen,Pontillo, Joseph,Fleck, Beth A.,Gao, Yinghong,Wen, Jenny,Tran, Joe A.,Tucci, Fabio C.,Marinkovic, Dragan,Foster, Alan C.,Saunders, John. "4-{(2R-[3-Aminopropionylamido]-3-(2,4-dichlorophenyl)propionyl} -1-{2-[(2-thienyl)ethylaminomethyl]phenyl}piperazine as a potent and selective melanocortin-4 receptor antagonist - Design, synthesis, and characterization". . p. 6821 - 6830. Retrieved 2007/10/03.