tert-butyl 4-[N-[7-chloro-3-methyl-2-morpholinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Base Information

• Chemical Name: tert-butyl 4-[N-[7-chloro-3-methyl-2-morpholinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate
• CAS No.: 289686-93-7
• Molecular Formula: C₂₉H₃₃ClN₄O₄
• Molecular Weight: 537.058
• Mol file: 289686-93-7.mol

Synonyms:tert-butyl 4-[N-[7-chloro-3-methyl-2-morpholinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Chemical Property of tert-butyl 4-[N-[7-chloro-3-methyl-2-morpholinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-[N-[7-chloro-3-methyl-2-morpholinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

There total 19 articles about tert-butyl 4-[N-[7-chloro-3-methyl-2-morpholinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate 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: 82.0%

morpholine (110-91-8,99108-56-2) + tert-butyl 4-[N-[7-chloro-2-methanesulfonyloxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289686-89-1) → tert-butyl 4-[N-[7-chloro-3-methyl-2-morpholinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289686-93-7)

Guidance literature:

In dichloromethane; at 20 ℃;

DOI:10.1021/jm011081s

Reference yield:

3-chloro-p-toluidine (95-74-9,827571-80-2) → tert-butyl 4-[N-[7-chloro-3-methyl-2-morpholinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289686-93-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 86 percent / pyridine / ethyl acetate / 18 h / 20 °C

2: 48 percent / glacial AcOH; Br₂ / 1.5 h / 15 °C

3: 94 percent / AcOH; conc. HCl / 24 h / 118 °C

4: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C

5: 93 percent / aq. KOH; H₂O₂ / 2 h / 130 °C

6: 97 percent / tetrahydrofuran / 6 h / 20 °C

7: 90 percent / DMAP / 3 h / 80 °C

8: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C

9: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C

10: 76 percent / 48percent aq. HBr / 7 h / 120 °C

11: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

12: 51 percent / NBS; dibenzoyl peroxide / CCl₄ / 3.83 h / 85 °C / Irradiation

13: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C

14: 80 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C

15: 94 percent / Et₃N / CH₂Cl₂ / 0.92 h

16: 82 percent / CH₂Cl₂ / 20 °C

With pyridine; 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; N-Bromosuccinimide; dihydrogen peroxide; bromine; acetic acid; triethylamine; dibenzoyl peroxide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm011081s

Reference yield:

2-bromo-5-chloro-4-methylaniline (102170-52-5) → tert-butyl 4-[N-[7-chloro-3-methyl-2-morpholinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (289686-93-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 6.52 g / N-methylpyrrolidinone / 2 h / 163 °C

2: 93 percent / aq. KOH; H₂O₂ / 2 h / 130 °C

3: 97 percent / tetrahydrofuran / 6 h / 20 °C

4: 90 percent / DMAP / 3 h / 80 °C

5: 90 percent / pyridine / dimethylformamide / 2 h / 20 °C

6: 0.230 g / methanol; tetrahydrofuran / 26 h / 20 °C

7: 76 percent / 48percent aq. HBr / 7 h / 120 °C

8: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

9: 51 percent / NBS; dibenzoyl peroxide / CCl₄ / 3.83 h / 85 °C / Irradiation

10: 73 percent / 2,6-lutidine / dimethylformamide / 5.5 h / 120 °C

11: 80 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C

12: 94 percent / Et₃N / CH₂Cl₂ / 0.92 h

13: 82 percent / CH₂Cl₂ / 20 °C

With pyridine; 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; dmap; potassium hydroxide; sodium hydroxide; N-Bromosuccinimide; dihydrogen peroxide; triethylamine; dibenzoyl peroxide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm011081s

upstream raw materials:

morpholine

tert-butyl 4-[N-[7-chloro-2-methanesulfonyloxymethyl-3-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate

N-(3-chloro-4-methylphenyl)acetamide

2-bromo-5-chloro-4-methylaniline

Refernces

• 1、 Bavetsias,Skelton,Yafai,Mitchell,Wilson,Allan,Jackman. "The design and synthesis of water-soluble analogues of CB30865, a quinazolin-4-one-based antitumor agent". . p. 3692 - 3702. Retrieved 2007/10/03.