1-((S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propyl)-3-((S)-1-(thiophen-3-yl)propan-2-yl)urea

Base Information

• Chemical Name: 1-((S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propyl)-3-((S)-1-(thiophen-3-yl)propan-2-yl)urea
• CAS No.: 1997387-43-5
• Molecular Formula: C₁₉H₂₇N₃O₂S
• Molecular Weight: 361.508
• Mol file: 1997387-43-5.mol

Synonyms:

Chemical Property of 1-((S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propyl)-3-((S)-1-(thiophen-3-yl)propan-2-yl)urea

Chemical Property:

• Boiling Point: 583.8±50.0 °C(Predicted)
• PKA: 10.06±0.15(Predicted)
• Density: 1.169±0.06 g/cm3(Predicted)

Purity/Quality:

99%+, ^*data from raw suppliers

PZM21 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: PZM21 is a potent Gi activator with exceptional selectivity for μOR and minimal β-arrestin-2 recruitment. PZM21 is an experimental opioid analgesic drug that is being researched for the treatment of pain. It is a functionally selective μ-opioid receptor agonist which produces μ-opioid receptor mediated G protein signaling, with potency and efficacy similar to morphine, but with less β-arrestin 2 recruitment. In tests on mice, PZM21 was slightly less potent than morphine or TRV130 as an analgesic, but also had significantly reduced adverse effects, with less constipation than morphine, and very little respiratory depression, even at high doses.

Technology Process of 1-((S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propyl)-3-((S)-1-(thiophen-3-yl)propan-2-yl)urea

There total 40 articles about 1-((S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propyl)-3-((S)-1-(thiophen-3-yl)propan-2-yl)urea 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: 71.0%

methanol (67-56-1) + 3-[(2S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propyl]-1-(4-methylbenzenesulfonyl)-1-[(2S)-1-(thiophen-3-yl)propan-2-yl]urea → 1-[(2S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propyl]-3-[(2S)-1-(thiophen-3-yl)propan-2-yl]urea (1997387-43-5) + C13H20N2O3 + 4-methyl-N-[(2S)-1-(thiophen-3-yl)propan-2-yl]benzene-1-sulfonamide

Guidance literature:

With magnesium; at 20 ℃; for 1h; Sonication;

DOI:10.1002/ejoc.201800517

Reference yield: 60.0%

(S)-4-[3-amino-2-(dimethylamino)propyl]phenol dihydrochloride (2007916-74-5) + (2S)-1-(thiophen-3-yl)propan-2-amine hydrochloride → 1-[(2S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propyl]-3-[(2S)-1-(thiophen-3-yl)propan-2-yl]urea (1997387-43-5)

Guidance literature:

(2S)-1-(thiophen-3-yl)propan-2-amine hydrochloride; With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; In acetonitrile; at 20 ℃; for 0.25h;

(S)-4-[3-amino-2-(dimethylamino)propyl]phenol dihydrochloride; In acetonitrile; at 20 ℃; for 16h; Solvent; Reagent/catalyst;

DOI:10.1002/ejoc.201800517

Reference yield:

4-nitrophenyl (RS)-[1-(thiophen-3-yl)propan-2-yl]carbamate + (S)-4-[3-amino-2-(dimethylamino)propyl]phenol dihydrochloride (2007916-74-5) → 1-[(S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propyl]-3-((R)-1-(thiophen-3-yl)propan-2-yl)urea (1997387-43-5) + 1-[(2S)-2-(dimethylamino)-3-(4-hydroxyphenyl)propyl]-3-[(2S)-1-(thiophen-3-yl)propan-2-yl]urea (1997387-43-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 20h; Overall yield = 70 %; Overall yield = 100 mg; Inert atmosphere;

upstream raw materials:

3-thiophene carboxaldehyde

(E)-3-(2-nitroprop-1-en-1-yl)thiophene

(S)-4-[3-amino-2-(dimethylamino)propyl]phenol dihydrochloride

(RS)-1-(thiophen-3-yl)propan-2-amine hydrochloride

Refernces

• 1、 Perrey, David,Zhang, Dehui,Nguyen, Thuy,Carroll, F. Ivy,Ko, Mei-Chuan,Zhang, Yanan. "Synthesis of Enantiopure PZM21: A Biased Agonist of the Mu-Opioid Receptor". . p. 4006 - 4012. Retrieved 2018/07/30.