Prenalterol

Base Information

• Chemical Name: Prenalterol
• CAS No.: 57526-81-5
• Deprecated CAS: 58165-86-9
• Molecular Formula: C12H19 N O3
• Molecular Weight: 225.288
• European Community (EC) Number: 260-791-5
• UNII: M4G34404CX
• DSSTox Substance ID: DTXSID8023507
• Nikkaji Number: J11.867B
• Wikipedia: Prenalterol
• Wikidata: Q7240518
• NCI Thesaurus Code: C174691
• Pharos Ligand ID: SGM2TV732TQ8
• Metabolomics Workbench ID: 67746
• ChEMBL ID: CHEMBL1160714
• Mol file: 57526-81-5.mol

Synonyms:A Ba C 50,005;A-Ba-C-50,005;ABaC50,005;H-133-22;H-80-62;H13322;H8062;Hydrochloride, Prenalterol;KWD-2033;KWD2033;Prenalterol;Prenalterol Hydrochloride

Chemical Property of Prenalterol

Chemical Property:

• Vapor Pressure: 4.86E-07mmHg at 25°C
• Melting Point: 127-128°
• Boiling Point: 397.7°Cat760mmHg
• PKA: pKa 9.5 (Uncertain);10.0 (Uncertain)
• Flash Point: 194.3°C
• PSA: 61.72000
• Density: 1.118g/cm³
• LogP: 1.52080
• Storage Temp.: 2-8°C
• Solubility.: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 225.13649347
• Heavy Atom Count: 16
• Complexity: 179

Purity/Quality:

98%Min ^*data from raw suppliers

Prenalterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=C(C=C1)O)O
• Isomeric SMILES: CC(C)NC[C@@H](COC1=CC=C(C=C1)O)O
• Uses: Prenalterol is a β1-adrenergic agonist. Prenalterol is used as an cardiotonic. Prenalterol is a β1-adrenergic agonist and used as an cardiotonic (1,2,3).

Technology Process of Prenalterol

There total 24 articles about Prenalterol 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: 92.3%

(2S)-1-<4-(benzyloxy)phenoxy>-3-<(1-methylethyl)amino>-2-propanol (57526-82-6) → prenalterol (57526-81-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 0.666667h; under 760 Torr; Ambient temperature;

DOI:10.1021/jm00365a004

Reference yield: 89.0%

isopropylamine (75-31-0) + (S)-4-(2,3-epoxypropoxy)phenol (730984-83-5) → prenalterol (57526-81-5)

Guidance literature:

With water; Reflux;

DOI:10.1016/j.mencom.2019.03.028

Reference yield:

(S)-N-isopropyl-2,3-O-isopropylidene-D-glyceraldimine (86955-00-2) → prenalterol (57526-81-5)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂ / 10percent Pd/C / 760 Torr / Ambient temperature

2: 95 percent / triethylamine / CH₂Cl₂ / 0.5 h / 10 - 15 °C

3: 84.6 percent / Dowex₅₀W-8x ion-exchange resin (H⁺ form / aq. ethanol / 1.5 h / Heating

4: 264 g / benzoic acid / 0.5 h

5: 268 g / trimethylchlorosilane / CH₂Cl₂ / 0.75 h / Heating

6: 182 g / aq. NaOH / methanol / 0.5 h / 15 °C

7: 92 percent / Na, MeOH / 16 h / Heating

8: POCl₃ / toluene / 1.5 h / Ambient temperature

9: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1.5 h / 80 °C

10: 92.3 percent / H₂ / 10percent Pd/C / methanol / 0.67 h / 760 Torr / Ambient temperature

With methanol; sodium hydroxide; chloro-trimethyl-silane; Dowex₅₀W-8x ion-exchange resin (H⁺ form; hydrogen; sodium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; benzoic acid; trichlorophosphate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; toluene;

DOI:10.1021/jm00365a004

upstream raw materials:

(2S)-1-<4-(benzyloxy)phenoxy>-3-<(1-methylethyl)amino>-2-propanol

4-Benzyloxyphenol

(S)-5-hydroxymethyl-3-(methylethyl)oxazolidinone

(S)-3-isopropyl-5-p-toluenesulfonyloxymethyl-oxazolidin-2-one

Downstream raw materials:

(S)-1-(4-{12-[4-((S)-2-Hydroxy-3-isopropylamino-propoxy)-phenoxy]-dodecyloxy}-phenoxy)-3-isopropylamino-propan-2-ol

(S)-1-(4-{14-[4-((S)-2-Hydroxy-3-isopropylamino-propoxy)-phenoxy]-tetradecyloxy}-phenoxy)-3-isopropylamino-propan-2-ol

(S)-1-[4-(2-{2-[4-((S)-2-Hydroxy-3-isopropylamino-propoxy)-phenoxy]-ethoxy}-ethoxy)-phenoxy]-3-isopropylamino-propan-2-ol

(S)-1-(4-{2-[2-(2-{2-[4-((S)-2-Hydroxy-3-isopropylamino-propoxy)-phenoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-phenoxy)-3-isopropylamino-propan-2-ol

Refernces

• 1、 -. "METHODS FOR DIAGNOSING, MONITORING AND TREATING NEUROLOGICAL DISEASES AND DISORDERS". . . Retrieved 2020/01/08.
• 2、 -. "Substituted (10H-phenothiazin-10-L)-propyl-1-piperazines". . . Retrieved 2008/06/13.