(1R)-trans-4-[N-Boc-1-aminoethyl]-N-4-pyridinyl-cyclohexanecarboxamide

Base Information

• Chemical Name: (1R)-trans-4-[N-Boc-1-aminoethyl]-N-4-pyridinyl-cyclohexanecarboxamide
• CAS No.: 671816-04-9
• Molecular Formula: C19H29N3O3
• Molecular Weight: 347.458
• Mol file: 671816-04-9.mol

Synonyms:(1R)-trans-4-[N-Boc-1-aminoethyl]-N-4-pyridinyl-cyclohexanecarboxamide;trans-tert-butyl (R)-1-[4-(pyridin-4-ylcarbamoyl)cyclohexyl]ethylcarbamate;[(1R)-1-[trans-4-[(4-Pyridinylamino)carbonyl]cyclohexyl]ethyl]carbamic Acid 1,1-Dimethylethyl Ester;(R)-trans-4-[N'-(tert-butyloxycarbonyl)ethan-1'-amino]-N-(4''-pyridyl)cyclohexanecarboxamide;

Chemical Property of (1R)-trans-4-[N-Boc-1-aminoethyl]-N-4-pyridinyl-cyclohexanecarboxamide

Chemical Property:

• Melting Point: 90-92°C
• Boiling Point: 547.3±20.0 °C(Predicted)
• PKA: 12.50±0.46(Predicted)
• PSA: 87.04000
• Density: 1.125±0.06 g/cm3(Predicted)
• LogP: 3.36600
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

NLT 98% ^*data from raw suppliers

(1R)-trans-4-[N-Boc-1-aminoethyl]-N-4-pyridinyl-cyclohexanecarboxamide(~90%R) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Protected Y-27632, a Rho kinase inhibitor (ROCK) for the treatment of ischemia-reperfusion disorders.

Technology Process of (1R)-trans-4-[N-Boc-1-aminoethyl]-N-4-pyridinyl-cyclohexanecarboxamide

There total 24 articles about (1R)-trans-4-[N-Boc-1-aminoethyl]-N-4-pyridinyl-cyclohexanecarboxamide 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: 97.0%

4-aminopyridine (504-24-5) + (1R,4r)-4-((R)-1-((tert-butoxycarbonyl)amino)ethyl)cyclohexanecarboxylic acid (671815-99-9) → trans-tert-butyl (R)-1-[4-(pyridin-4-ylcarbamoyl)cyclohexyl]ethylcarbamate (671816-04-9)

Guidance literature:

With 2-chloro-1-methyl-pyridinium iodide; triethylamine; In dichloromethane; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1039/c1ob05332a

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → trans-tert-butyl (R)-1-[4-(pyridin-4-ylcarbamoyl)cyclohexyl]ethylcarbamate (671816-04-9)

Guidance literature:

Multi-step reaction with 4 steps

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

2: TBAF / tetrahydrofuran / 0 °C

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

4: TBTU; DIEA / dimethylformamide / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; sodium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; phosphate buffer; In tetrahydrofuran; 1,2-dimethoxyethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmcl.2004.07.025

Reference yield:

trans-[4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-methanol (141836-50-2) → trans-tert-butyl (R)-1-[4-(pyridin-4-ylcarbamoyl)cyclohexyl]ethylcarbamate (671816-04-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / PCC / CH₂Cl₂

2: MgSO₄ / CH₂Cl₂

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

4: HCO₂NH₄; Pd/C / methanol / Heating

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

6: TBAF / tetrahydrofuran / 0 °C

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

8: TBTU; DIEA / dimethylformamide / 20 °C

With 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; 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:

4-aminopyridine

di-tert-butyl dicarbonate

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

4-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexane carbaldehyde

Downstream raw materials:

R-(+)-trans-4-(1-aminoethyl)-N-(4-pyridyl)-cyclohexanecarboxamide

(R)-(+)-trans-N-(4-pyridyl)-4-(1-aminoethyl)cyclohexanecarboxamide dihydrochloride

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