N¹-{2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethyl}-N²-(3,5-dinitrobenzoyl)leucinamide

Base Information

• Chemical Name: N¹-{2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethyl}-N²-(3,5-dinitrobenzoyl)leucinamide
• CAS No.: 479623-43-3
• Molecular Formula: C₃₃H₃₇N₉O₇
• Molecular Weight: 671.713

Synonyms:N¹-{2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethyl}-N²-(3,5-dinitrobenzoyl)leucinamide

Chemical Property of N¹-{2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethyl}-N²-(3,5-dinitrobenzoyl)leucinamide

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Technology Process of N¹-{2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethyl}-N²-(3,5-dinitrobenzoyl)leucinamide

There total 4 articles about N¹-{2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethyl}-N²-(3,5-dinitrobenzoyl)leucinamide 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: 38.0%

(S)-N-(3,5-dinitrobenzoyl)leucine (7495-01-4) + 2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethylamine (385366-63-2) → N1-{2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethyl}-N2-(3,5-dinitrobenzoyl)leucinamide (479623-43-3)

Guidance literature:

(S)-N-(3,5-dinitrobenzoyl)leucine; With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In tetrahydrofuran; at 20 ℃; for 3h;

2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethylamine; In tetrahydrofuran; at 20 ℃; for 15h;

DOI:10.1002/1099-0690(200109)2001:18<3523::AID-EJOC3523>3.0.CO;2-#

Reference yield:

[2-(4,6-Dichloro-[1,3,5]triazin-2-yloxy)-ethyl]-carbamic acid tert-butyl ester → N1-{2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethyl}-N2-(3,5-dinitrobenzoyl)leucinamide (479623-43-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2 g / diisopropyl(ethyl)amine / acetonitrile / 24 h / 20 °C

2.1: 91 percent / acetonitrile / 20 h / 50 °C

3.1: 100 percent / TFA / CH₂Cl₂ / 0.25 h / 20 °C

4.1: 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline / tetrahydrofuran / 3 h / 20 °C

4.2: 38 percent / tetrahydrofuran / 15 h / 20 °C

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/1099-0690(200109)2001:18<3523::AID-EJOC3523>3.0.CO;2-#

Reference yield:

tert-butyl 2-(4-chloro-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy)ethylcarbamate (385366-61-0) → N1-{2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethyl}-N2-(3,5-dinitrobenzoyl)leucinamide (479623-43-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91 percent / acetonitrile / 20 h / 50 °C

2.1: 100 percent / TFA / CH₂Cl₂ / 0.25 h / 20 °C

3.1: 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline / tetrahydrofuran / 3 h / 20 °C

3.2: 38 percent / tetrahydrofuran / 15 h / 20 °C

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/1099-0690(200109)2001:18<3523::AID-EJOC3523>3.0.CO;2-#

upstream raw materials:

(S)-N-(3,5-dinitrobenzoyl)leucine

2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethylamine

tert-butyl 2-(4-chloro-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy)ethylcarbamate

tert-butyl 2-[4-(allylamino)-6-{[(1S)-1-(1-naphthyl)ethyl]amino}-1,3,5-triazin-2-yloxy]ethylcarbamate

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