Y-27632 dihydrochloride

Base Information

• Chemical Name: Y-27632 dihydrochloride
• CAS No.: 129830-38-2
• Molecular Formula: C14H23Cl2N3O
• Molecular Weight: 320.25792
• Hs Code.: 29333990
• European Community (EC) Number: 813-428-5
• UNII: Q9828II7F3
• DSSTox Substance ID: DTXSID3042635
• Wikidata: Q27287129
• ChEMBL ID: CHEMBL536267,CHEMBL1605605
• Mol file: 129830-38-2.mol

Synonyms:N-(4-pyridyl)-4-(1-aminoethyl)cyclohexanecarboxamide;Y 27632;Y 27632, (4(R)-trans)-isomer;Y 27632, (4(S)-trans)-isomer;Y 27632, (trans)-isomer;Y 27632, dihydrochloride, (4(R)-trans)-isomer;Y-27632;Y27632

Chemical Property of Y-27632 dihydrochloride

Chemical Property:

• Melting Point: 258℃
• PSA: 68.01000
• LogP: 4.55100
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble14mg/mL
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 319.1218178
• Heavy Atom Count: 20
• Complexity: 268

Purity/Quality:

98.0%Min ^*data from raw suppliers

Y 27632 Dihydrochloride ≥98%(HPLC)Containsapprox.1.4%water. ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C1CCC(CC1)C(=O)NC2=CC=NC=C2)N.Cl.Cl
• Isomeric SMILES: C[C@H](C1CCC(CC1)C(=O)NC2=CC=NC=C2)N.Cl.Cl
• Description: Y-27632 dihydrochloride (129830-38-2) is a specific inhibitor of ROCK family kinases.1 Enhances stem cell survival and proliferation in culture.2 Y-27632 dihydrochloride significantly improves freeze/thaw survival rate for human embryonic stem cells without influencing morphology, karyotype, cell surface markers, or differentiation potential.3
• Uses: A cell permeable inhibitor of ROCK-1 and ROCK-2 Y-27632 dihydrochloride has been used:as a medium supplement in pancreatic ductal adenocarcinoma organoid culturein the inhibition of Ras homolog gene family (Rho) kinase in mouse embryonic stem cellsin the inhibition of Rho-associated protein kinase (ROCK) in human embryonic stem cells and human induced pluripotent stem cells (iPSCs)

Technology Process of Y-27632 dihydrochloride

There total 30 articles about Y-27632 dihydrochloride 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: 95.0%

trans-tert-butyl (R)-1-[4-(pyridin-4-ylcarbamoyl)cyclohexyl]ethylcarbamate (671816-04-9) → (R)-(+)-trans-N-(4-pyridyl)-4-(1-aminoethyl)cyclohexanecarboxamide dihydrochloride (129830-38-2)

Guidance literature:

With hydrogenchloride; In diethyl ether; dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c1ob05332a

Reference yield:

(S)-trans-4-[N'-(tert-butyloxycarbonyl)ethan-1'-amino]-N-(4''-pyridyl)cyclohexanecarboxamide (671816-05-0) → (-)-Y-27632 (129830-38-2)

Guidance literature:

With hydrogenchloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2004.07.025

Reference yield:

bis-1,4-(hydroxymethyl)cyclohexane (105-08-8) → (R)-(+)-trans-N-(4-pyridyl)-4-(1-aminoethyl)cyclohexanecarboxamide dihydrochloride (129830-38-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 61 percent / Et₃N; DMAP

2: 80 percent / PCC / CH₂Cl₂

3: MgSO₄ / CH₂Cl₂

4: CuI; BF₃*Et₂O / tetrahydrofuran / -65 - -30 °C

5: HCO₂NH₄; Pd/C / methanol / Heating

6: aq. NaHCO₃; Na₂CO₃ / 1,2-dimethoxy-ethane

7: TBAF / tetrahydrofuran / 0 °C

8: TEMPO; NaClO₂; NaOCl / aq. phosphate buffer / acetonitrile / 35 °C

9: TBTU; DIEA / dimethylformamide / 20 °C

10: HCl(g) / CH₂Cl₂ / 0 - 20 °C

With hydrogenchloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; palladium on activated charcoal; copper(l) iodide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; ammonium formate; sodium hydrogencarbonate; sodium carbonate; magnesium sulfate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; phosphate buffer; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmcl.2004.07.025

upstream raw materials:

trans-tert-butyl (R)-1-[4-(pyridin-4-ylcarbamoyl)cyclohexyl]ethylcarbamate

4-aminopyridine

bis-1,4-(hydroxymethyl)cyclohexane

trans-[4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-methanol

Refernces

• 1、 Gingras, Karine,Avedissian, Hovsep,Thouin, Eryk,Boulanger, Véronique,Essagian, Charles,McKerracher, Lisa,Lubell, William D.. "Synthesis and evaluation of 4-(1-aminoalkyl)-N-(4-pyridyl) cyclohexanecarboxamides as Rho kinase inhibitors and neurite outgrowth promoters". . p. 4931 - 4934. Retrieved 2007/10/03.