N-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexylmethyl]-2-(2-trifluoromethoxy-phenyl)-acetamide

Base Information

• Chemical Name: N-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexylmethyl]-2-(2-trifluoromethoxy-phenyl)-acetamide
• CAS No.: 509143-10-6
• Molecular Formula: C₂₆H₃₀F₃N₅O₂
• Molecular Weight: 501.552
• Mol file: 509143-10-6.mol

Synonyms:

Chemical Property of N-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexylmethyl]-2-(2-trifluoromethoxy-phenyl)-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexylmethyl]-2-(2-trifluoromethoxy-phenyl)-acetamide

There total 13 articles about N-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexylmethyl]-2-(2-trifluoromethoxy-phenyl)-acetamide 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:

cis-(4-aminomethyl-cyclohexyl)-carbamic acid tert-butyl ester (509143-00-4) → N-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexylmethyl]-2-(2-trifluoromethoxy-phenyl)-acetamide (509143-10-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 25.3 g / triethylamine / CH₂Cl₂ / 16 h / 20 °C

2: 95 percent / hydrogen chloride / ethyl acetate / 3 h / 20 °C

3: 84 percent / propan-2-ol / 168 h / Heating

4: hydrogen / Pd-C / methanol / 60 h / 50 °C

5: 396 mg / iPr₂NEt / CH₂Cl₂ / 5 h / 4 °C

With hydrogenchloride; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; isopropyl alcohol;

DOI:10.1016/j.bmc.2005.12.052

Reference yield:

cis-4-(tert-butoxycarbonylamino)cyclohexanecarboxylic acid methyl ester (364385-64-8) → N-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexylmethyl]-2-(2-trifluoromethoxy-phenyl)-acetamide (509143-10-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 301 g / lithium aluminum hydride / diethyl ether / 2 h / 20 °C

2: 27.5 g / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 60 h / 20 °C

3: hydrazine hydrate / ethanol / 2.25 h / Heating

4: 25.3 g / triethylamine / CH₂Cl₂ / 16 h / 20 °C

5: 95 percent / hydrogen chloride / ethyl acetate / 3 h / 20 °C

6: 84 percent / propan-2-ol / 168 h / Heating

7: hydrogen / Pd-C / methanol / 60 h / 50 °C

8: 396 mg / iPr₂NEt / CH₂Cl₂ / 5 h / 4 °C

With hydrogenchloride; lithium aluminium tetrahydride; hydrogen; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; isopropyl alcohol; toluene;

DOI:10.1016/j.bmc.2005.12.052

Reference yield:

cis-(4-amino-cyclohexylmethyl)-carbamic acid benzyl ester (509142-55-6) → N-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexylmethyl]-2-(2-trifluoromethoxy-phenyl)-acetamide (509143-10-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / propan-2-ol / 168 h / Heating

2: hydrogen / Pd-C / methanol / 60 h / 50 °C

3: 396 mg / iPr₂NEt / CH₂Cl₂ / 5 h / 4 °C

With hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; isopropyl alcohol;

DOI:10.1016/j.bmc.2005.12.052

upstream raw materials:

2-trifluoromethoxyphenylacetyl chloride

N²-[cis-4-(aminomethyl)cyclohexyl]-N⁴,N⁴-dimethylquinazoline-2,4-diamine

2-[2-(trifluoromethoxy)phenyl]acetic acid

cis-(4-aminomethyl-cyclohexyl)-carbamic acid tert-butyl ester