N²-[4-[N-[[3,4-dihydro-2,7-dimethyl-4-oxo-3-[(pivaloyloxy)methyl]-6-quinazolinyl]methyl]-N-prop-2-ynylamino]-2-fluorobenzoyl]-N⁵-(methanesulfonyl)-L-glutamine

Base Information

• Chemical Name: N²-[4-[N-[[3,4-dihydro-2,7-dimethyl-4-oxo-3-[(pivaloyloxy)methyl]-6-quinazolinyl]methyl]-N-prop-2-ynylamino]-2-fluorobenzoyl]-N⁵-(methanesulfonyl)-L-glutamine
• CAS No.: 247904-31-0
• Molecular Formula: C₃₃H₃₈FN₅O₉S
• Molecular Weight: 699.757

Synonyms:N²-[4-[N-[[3,4-dihydro-2,7-dimethyl-4-oxo-3-[(pivaloyloxy)methyl]-6-quinazolinyl]methyl]-N-prop-2-ynylamino]-2-fluorobenzoyl]-N⁵-(methanesulfonyl)-L-glutamine

Chemical Property of N²-[4-[N-[[3,4-dihydro-2,7-dimethyl-4-oxo-3-[(pivaloyloxy)methyl]-6-quinazolinyl]methyl]-N-prop-2-ynylamino]-2-fluorobenzoyl]-N⁵-(methanesulfonyl)-L-glutamine

Chemical Property:

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Technology Process of N²-[4-[N-[[3,4-dihydro-2,7-dimethyl-4-oxo-3-[(pivaloyloxy)methyl]-6-quinazolinyl]methyl]-N-prop-2-ynylamino]-2-fluorobenzoyl]-N⁵-(methanesulfonyl)-L-glutamine

There total 3 articles about N²-[4-[N-[[3,4-dihydro-2,7-dimethyl-4-oxo-3-[(pivaloyloxy)methyl]-6-quinazolinyl]methyl]-N-prop-2-ynylamino]-2-fluorobenzoyl]-N⁵-(methanesulfonyl)-L-glutamine 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: 48.0%

pentafluorophenyl 4--6-quinazolinyl>methyl>-N-prop-2-ynylamino>-2-fluorobenzoate (153538-13-7) + N5-(methanesulfonyl)-L-glutamine (173724-40-8) → N2-[4-[N-[[3,4-dihydro-2,7-dimethyl-4-oxo-3-[(pivaloyloxy)methyl]-6-quinazolinyl]methyl]-N-prop-2-ynylamino]-2-fluorobenzoyl]-N5-(methanesulfonyl)-L-glutamine (247904-31-0)

Guidance literature:

With benzotriazol-1-ol; triethylamine; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 20 ℃; for 0.75h;

DOI:10.1021/jm9803727

Reference yield:

Cbz-(L)-Glu-OBn (3705-42-8) → N2-[4-[N-[[3,4-dihydro-2,7-dimethyl-4-oxo-3-[(pivaloyloxy)methyl]-6-quinazolinyl]methyl]-N-prop-2-ynylamino]-2-fluorobenzoyl]-N5-(methanesulfonyl)-L-glutamine (247904-31-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

2: 29 percent / H₂ / 10 percent Pd/C / acetic acid / 2 h / 20 °C

3: 48 percent / HOBT; Et₃N / dimethylformamide; dimethylsulfoxide / 0.75 h / 20 °C

With dmap; hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrogenation / 3: Condensation;

DOI:10.1021/jm9803727

Reference yield:

N2-(benzyloxycarbonyl)-N5-(methanesulfonyl)-L-glutamine benzyl ester (247904-30-9) → N2-[4-[N-[[3,4-dihydro-2,7-dimethyl-4-oxo-3-[(pivaloyloxy)methyl]-6-quinazolinyl]methyl]-N-prop-2-ynylamino]-2-fluorobenzoyl]-N5-(methanesulfonyl)-L-glutamine (247904-31-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 29 percent / H₂ / 10 percent Pd/C / acetic acid / 2 h / 20 °C

2: 48 percent / HOBT; Et₃N / dimethylformamide; dimethylsulfoxide / 0.75 h / 20 °C

With hydrogen; benzotriazol-1-ol; triethylamine; palladium on activated charcoal; In acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Hydrogenation / 2: Condensation;

DOI:10.1021/jm9803727

upstream raw materials:

pentafluorophenyl 4--6-quinazolinyl>methyl>-N-prop-2-ynylamino>-2-fluorobenzoate

N⁵-(methanesulfonyl)-L-glutamine

Cbz-(L)-Glu-OBn

N²-(benzyloxycarbonyl)-N⁵-(methanesulfonyl)-L-glutamine benzyl ester

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