Ibutamoren mesylate

Base Information

• Chemical Name: Ibutamoren mesylate
• CAS No.: 159752-10-0
• Deprecated CAS: 214962-40-0
• Molecular Formula: CH₄O₃S*C₂₇H₃₆N₄O₅S
• Molecular Weight: 624.78
• UNII: R90JB6QJ2B
• DSSTox Substance ID: DTXSID50936168
• Wikidata: Q27287984
• NCI Thesaurus Code: C97489
• RXCUI: 1805437
• ChEMBL ID: CHEMBL2105872
• Mol file: 159752-10-0.mol

Synonyms:ibutamoren mesylate;L 163,191;L 163191;L-163,191;L-163191;MK 0677;MK-0677;MK-677

Chemical Property of Ibutamoren mesylate

Chemical Property:

• Boiling Point: 868.9 °C at 760 mmHg
• Flash Point: 479.3 °C
• PSA: 196.66000
• LogP: 4.97440
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble5mg/mL, clear
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 624.22875659
• Heavy Atom Count: 42
• Complexity: 1010

Purity/Quality:

98% ^*data from raw suppliers

MK-677 ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C(=O)NC(COCC1=CC=CC=C1)C(=O)N2CCC3(CC2)CN(C4=CC=CC=C34)S(=O)(=O)C)N.CS(=O)(=O)O
• Isomeric SMILES: CC(C)(C(=O)N[C@H](COCC1=CC=CC=C1)C(=O)N2CCC3(CC2)CN(C4=CC=CC=C34)S(=O)(=O)C)N.CS(=O)(=O)O
• Recent ClinicalTrials: Growth Hormone Secretagogue MK-0677's Effect on Lean Body Mass in Chronic Kidney Disease Stage 4/5 Subjects
• Recent EU Clinical Trials: An Open-Label, Multicenter, Phase 2 Study to Evaluate Growth and Safety of LUM-201 Following 12 Months of Daily rhGH Treatment in Children with Idiopathic Growth Hormone Deficiency who have Previously Completed the LUM-201-01 Trial
• Description: MK-677?(also known as ibutamoren),?promotes the secretion of the growth hormone (GH)?and?increases insulin-like growth factor 1 (IGF-1). Ibutamoren increases growth hormone levels by mimicking the action of the hormone?ghrelin?and binding to one of the ghrelin receptors (GHSR) in the brain. Activated GHSR stimulates growth hormone release from the brain. Clinical studies describe only the effects ibutamoren has on?appetite and as expected, like ghrelin, ibutamoren increases it. GHSR is found in brain regions that control appetite, pleasure, mood, biological rhythms, memory, and cognition.
• Uses: Growth hormone releasing factor.MK-677 is a potent, non-peptide ghrelin receptor agonist.

Technology Process of Ibutamoren mesylate

There total 27 articles about Ibutamoren mesylate 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:

isonipecotic acid (498-94-2) → MK-677 (191487-52-2,214962-40-0,159752-10-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 97 percent / K₂CO₃ / H₂O / 58 h / 22 °C

2: (COCl)2 / toluene; dimethylformamide / 16 h / 18 °C

3: 94 percent / H₂, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr

4: 99 percent / TFA / CH₂Cl₂ / 17 h / 35 °C

5: NaBH₄ / toluene / 0.5 h / -2 °C

6: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C

7: 93 percent / H₂ / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr

8: DCC, HOBt / H₂O; various solvent(s) / 5 h / Ambient temperature

9: MsOH / ethanol / 7.5 h / 35 - 40 °C

10: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature

11: MsOH / ethanol / 35 - 40 °C

12: ethanol; ethyl acetate / 55 °C

With sodium tetrahydroborate; oxalyl dichloride; methanesulfonic acid; methyl-phenyl-thioether; hydrogen; potassium carbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(97)00359-1

Reference yield:

N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde (138163-08-3) → MK-677 (191487-52-2,214962-40-0,159752-10-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 99 percent / TFA / CH₂Cl₂ / 17 h / 35 °C

2: NaBH₄ / toluene / 0.5 h / -2 °C

3: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C

4: 93 percent / H₂ / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr

5: DCC, HOBt / H₂O; various solvent(s) / 5 h / Ambient temperature

6: MsOH / ethanol / 7.5 h / 35 - 40 °C

7: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature

8: MsOH / ethanol / 35 - 40 °C

9: ethanol; ethyl acetate / 55 °C

With sodium tetrahydroborate; methanesulfonic acid; hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1016/S0040-4020(97)00359-1

Reference yield:

benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate (167484-18-6) → MK-677 (191487-52-2,214962-40-0,159752-10-0)

Guidance literature:

Multi-step reaction with 7 steps

1: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C

2: 93 percent / H₂ / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr

3: DCC, HOBt / H₂O; various solvent(s) / 5 h / Ambient temperature

4: MsOH / ethanol / 7.5 h / 35 - 40 °C

5: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature

6: MsOH / ethanol / 35 - 40 °C

7: ethanol; ethyl acetate / 55 °C

With methanesulfonic acid; hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; ethyl acetate;

DOI:10.1016/S0040-4020(97)00359-1

upstream raw materials:

isonipecotic acid

N-Boc-D-serine(Bzl)-OH

benzyl bromide

1-benzyloxycarbonylpiperidine-4-carboxylic acid

Refernces

• 1、 Qi, Xian Liang,Yang, Er Qun,Zhang, Jun Tao,Wang, Tao,Cao, Xiao Ping. "A facile synthesis of the spiroindoline-based growth hormone secretagogue, MK-677". . p. 661 - 664. Retrieved 2012/07/03.
• 2、 Maligres, Peter E.,Houpis, Ioannis,Rossen, Kai,Molina, Audrey,Sager, Jess,Upadhyay, Veena,Wells, Kenneth M.,Reamer, Robert A.,Lynch, Joseph E.,Askin, David,Volante,Reider, Paul J.,Houghton, Peter. "Synthesis of the orally active spiroindoline-based Growth Hormone Secretagogue, MK-677". . p. 10983 - 10992. Retrieved 2007/10/03.