Tert-butyl 4-(aminomethyl)-2,5-dimethylphenylcarbamate

Base Information

• Chemical Name: Tert-butyl 4-(aminomethyl)-2,5-dimethylphenylcarbamate
• CAS No.: 187163-72-0
• Molecular Formula: C12H19N3O2
• Molecular Weight: 237.302
• DSSTox Substance ID: DTXSID60700579
• Wikidata: Q82631997
• Mol file: 187163-72-0.mol

Synonyms:tert-butyl N-[4-(aminomethyl)-2,5-dimethylphenyl]carbamate;TERT-BUTYL 4-(AMINOMETHYL)-2,5-DIMETHYLPHENYLCARBAMATE;DTXSID60700579;AKOS015966435;A905060;tert-Butyl [4-(aminomethyl)-2,5-dimethylphenyl]carbamate

Chemical Property of Tert-butyl 4-(aminomethyl)-2,5-dimethylphenylcarbamate

Chemical Property:

• Vapor Pressure: 0.000228mmHg at 25°C
• Boiling Point: 325.6oC at 760 mmHg
• Flash Point: 150.7oC
• PSA: 64.35000
• Density: 1.083g/cm3
• LogP: 3.88240
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 250.168127949
• Heavy Atom Count: 18
• Complexity: 286

Purity/Quality:

99.3% ^*data from raw suppliers

tert-Butyl 5-(aminomethyl)-6-methylpyridin-2-ylcarbamate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1NC(=O)OC(C)(C)C)C)CN

Technology Process of Tert-butyl 4-(aminomethyl)-2,5-dimethylphenylcarbamate

There total 3 articles about Tert-butyl 4-(aminomethyl)-2,5-dimethylphenylcarbamate 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: 69.0%

2-tert-butoxycarbonylamino-5-cyano-6-methylpyridine (187163-71-9) → 2-tert-butoxycarbonylamino-5-aminomethyl-6-methyl-pyridine (187163-72-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 60h; under 3102.89 Torr;

DOI:10.1021/jm980368v

Reference yield:

5-bromo-6-methyl-pyridin-2-ylamine (42753-71-9) → 2-tert-butoxycarbonylamino-5-aminomethyl-6-methyl-pyridine (187163-72-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / dimethylformamide / 4 h / Heating

2: 84 percent / Et₃N, DMAP / CH₂Cl₂

3: 69 percent / H₂ / Pd/C / acetic acid / 60 h / 3102.89 Torr

With dmap; hydrogen; triethylamine; palladium on activated charcoal; In dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jm980368v

Reference yield:

2-amino-5-cyano-6-methylpyridine (183428-90-2) → 2-tert-butoxycarbonylamino-5-aminomethyl-6-methyl-pyridine (187163-72-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Et₃N, DMAP / CH₂Cl₂

2: 69 percent / H₂ / Pd/C / acetic acid / 60 h / 3102.89 Torr

With dmap; hydrogen; triethylamine; palladium on activated charcoal; In dichloromethane; acetic acid;

DOI:10.1021/jm980368v

upstream raw materials:

2-tert-butoxycarbonylamino-5-cyano-6-methylpyridine

5-bromo-6-methyl-pyridin-2-ylamine

2-amino-5-cyano-6-methylpyridine

Downstream raw materials:

2-(3-{[2,2-difluoro-2-(4-fluoronaphthyl)ethyl]amino}-6-chloro-2-fluorophenyl)-N-({6-[(tert-butoxy)carbonylamino]-2-methyl(3-pyridyl)}methyl)acetamide

2-{3-[(2,2-Difluoro-2-phenylethyl)amino]-6-chloro-2-fluorophenyl}-N-({6-[(tert-butoxy)carbonylamino]-2-methyl(3-pyridyl)}methyl) acetamide

3-(2-phenethylamino)-5-chloro-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)pyrazinone

3-benzyloxycarbonylamino-6-methyl-1-(2-tert-butoxycarbonylamino-6-methyl-5-methylenecarboxamidomethylpyridinyl)-2-pyridinone

Refernces

• 1、 Sanderson, Philip E. J.,Lyle, Terry A.,Cutrona, Kellie J.,Dyer, Dona L.,Dorsey, Bruce D.,McDonough, Colleen M.,Naylor-Olsen, Adel M.,Chen, I.-Wu,Chen, Zhongguo,Cook, Jacquelynn J.,Cooper, Carolyn M.,Gardell, Stephen J.,Hare, Timothy R.,Krueger, Julie A.,Lewis, S. Dale,Lin, Jiunn H.,Lucas Jr., Bobby J.,Lyle, Elizabeth A.,Lynch Jr., Joseph J.,Stranieri, Maria T.,Vastag, Kari,Yan, Youwei,Shafer, Jules A.,Vacca, Joseph P.. "Efficacious, orally bioavailable thrombin inhibitors based on 3- aminopyridinone or 3-aminopyrazinone acetamide peptidomimetic templates". . p. 4466 - 4474. Retrieved 2007/10/03.