(+)-(3'S,4S)-1-Benzyl-3-pyrrolidinyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

Base Information

• Chemical Name: (+)-(3'S,4S)-1-Benzyl-3-pyrrolidinyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
• CAS No.: 104713-75-9
• Molecular Formula: C27H29N3O6
• Molecular Weight: 491.544
• UNII: 2VBY96ASWJ
• Wikipedia: Barnidipine,Mepirodipine
• Wikidata: Q925327
• NCI Thesaurus Code: C73024
• Pharos Ligand ID: XY1VP2HUH899
• Metabolomics Workbench ID: 152260
• ChEMBL ID: CHEMBL2103761,CHEMBL2110040
• Mol file: 104713-75-9.mol

Synonyms:3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl(3S)-1-(phenylmethyl)-3-pyrrolidinyl ester, (4S)- (9CI);3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-,methyl 1-(phenylmethyl)-3-pyrrolidinyl ester, [S-(R*,R*)]-;Barnidipine;Hypoca;Mepirodipine;

Chemical Property of (+)-(3'S,4S)-1-Benzyl-3-pyrrolidinyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

Chemical Property:

• Vapor Pressure: 4.94E-15mmHg at 25°C
• Melting Point: 137-139°
• Refractive Index: 1.628
• Boiling Point: 614.5 °C at 760 mmHg
• PKA: 7.62±0.40(Predicted)
• Flash Point: 325.4 °C
• PSA: 113.69000
• Density: 1.31 g/cm³
• LogP: 4.61020
• Storage Temp.: 2-8°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 491.20563565
• Heavy Atom Count: 36
• Complexity: 917

Purity/Quality:

99% ^*data from raw suppliers

(S)-3-((S)-1-Benzylpyrrolidin-3-yl)-5-methyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(C(=C(N1)C)C(=O)OC2CCN(C2)CC3=CC=CC=C3)C4=CC(=CC=C4)[N+](=O)[O-])C(=O)OC
• Isomeric SMILES: CC1=C([C@@H](C(=C(N1)C)C(=O)O[C@H]2CCN(C2)CC3=CC=CC=C3)C4=CC(=CC=C4)[N+](=O)[O-])C(=O)OC
• Recent EU Clinical Trials: A RANDOMISED, DOUBLE-BLIND STUDY TO COMPARE THE EFFECT ON SYMPATHETIC ACTIVITY AND HEMODYNAMIC PROFILE OF BARNIDIPINE AND AMLODIPINE IN PATIENTS WITH MILD TO MODERATE ESSENTIAL HYPERTENSION.
• Therapeutic Function: Coronary vasodilator

Technology Process of (+)-(3'S,4S)-1-Benzyl-3-pyrrolidinyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

There total 18 articles about (+)-(3'S,4S)-1-Benzyl-3-pyrrolidinyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 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:

(R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (76093-33-9) + (S)-N-benzyl-3-hydroxypyrrolidine (101385-90-4) → barnidipine (104713-75-9)

Guidance literature:

at 50 ℃;

Reference yield:

(3S)-1-benzyl-3-hydroxypyrrolidine-2,5-dione (101469-91-4) → barnidipine (104713-75-9)

Guidance literature:

Multi-step reaction with 4 steps

1: boron trifluoride etherate, sodium borohydride / bis-(2-methoxy-ethyl) ether / 15 h / 100 °C

2: 1 h / 70 - 80 °C

3: 4.91 g / propan-2-ol / 8 h / Heating

With sodium tetrahydroborate; boron trifluoride diethyl etherate; In diethylene glycol dimethyl ether; isopropyl alcohol;

DOI:10.1021/jm00162a013

Reference yield:

benzylamine (100-46-9) → barnidipine (104713-75-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / ethanol / Heating

2: boron trifluoride etherate, sodium borohydride / bis-(2-methoxy-ethyl) ether / 15 h / 100 °C

3: 1 h / 70 - 80 °C

4: 4.91 g / propan-2-ol / 8 h / Heating

With sodium tetrahydroborate; boron trifluoride diethyl etherate; In ethanol; diethylene glycol dimethyl ether; isopropyl alcohol;

DOI:10.1021/jm00162a013

upstream raw materials:

(3RS)-1-benzyl-3-pyrrolidinyl methyl (4RS)2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride

1-benzyl-3-acetoacetyloxypyrrolidine

3-nitro-benzaldehyde

(+/-)-1-benzyl-3-pyrrolidinyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Downstream raw materials:

3-(R)-1-benzylpyrrolidin-3-yl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

[14C]-Barnidipine hydrochloride

2,6-Dimethyl-4-(3-nitro-phenyl)-pyridine-3,5-dicarboxylic acid 3-((S)-1-benzyl-pyrrolidin-3-yl) ester 5-methyl ester

Refernces

• 1、 Cheng, Zhi-Gang,Dai, Xu-Yong,Li, Li-Wei,Wan, Qiong,Ma, Xiang,Xiang, Guang-Ya. "Synthesis and characterization of impurities of barnidipine hydrochloride, an antihypertensive drug substance". . p. 1344 - 1352. Retrieved 2014/02/14.
• 2、 -. "ANTIHYPERTENSIVE THERAPY". . . Retrieved 2009/09/08.