N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]but-2-ynyloxymethyl}-2-hydroxybenzamidomethyl)doxorubicin

Base Information

Chemical Name:N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]but-2-ynyloxymethyl}-2-hydroxybenzamidomethyl)doxorubicin
CAS No.:636595-43-2
Molecular Formula:C₅₃H₅₀F₃N₅O₁₆
Molecular Weight:1070
Hs Code.:

N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]but-2-ynyloxymethyl}-2-hydroxybenzamidomethyl)doxorubicin

Synonyms:N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]but-2-ynyloxymethyl}-2-hydroxybenzamidomethyl)doxorubicin

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]but-2-ynyloxymethyl}-2-hydroxybenzamidomethyl)doxorubicin

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Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]but-2-ynyloxymethyl}-2-hydroxybenzamidomethyl)doxorubicin

There total 6 articles about N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]but-2-ynyloxymethyl}-2-hydroxybenzamidomethyl)doxorubicin 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:

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 25316-40-9
doxorubicin hydrochloride

: 636595-81-8
5-{4-[3-(4-cyano-3-trifluoromethyl-phenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]-but-2-ynyloxymethyl}-2-hydroxy-benzamide

: 636595-43-2
N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]but-2-ynyloxymethyl}-2-hydroxybenzamidomethyl)doxorubicin

Guidance literature:: formaldehyd; 5-{4-[3-(4-cyano-3-trifluoromethyl-phenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]-but-2-ynyloxymethyl}-2-hydroxy-benzamide; In water; N,N-dimethyl-formamide; at 55 ℃; for 0.25h;

doxorubicin hydrochloride; In water; N,N-dimethyl-formamide; at 55 ℃; for 0.25h;
DOI:10.1021/jm0303305

Reference yield:

: 77-71-4
5,5-dimethyl-imidazolidine-2,4-dione

: 636595-43-2
N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]but-2-ynyloxymethyl}-2-hydroxybenzamidomethyl)doxorubicin

Guidance literature:: Multi-step reaction with 4 steps

1.1: 60 percent / K₂CO₃ / dimethylformamide / 64 h / 55 - 65 °C

2.1: NaH / dimethylformamide / 3 h / 20 °C

2.2: 82 percent / dimethylformamide / 6 h / 20 °C

3.1: 80 percent / aq. p-TsOH / methanol / 24 h / 90 °C

4.1: dimethylformamide; H₂O / 0.25 h / 55 °C

4.2: dimethylformamide; H₂O / 0.25 h / 55 °C

With sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In methanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jm0303305

Reference yield:

: 76143-20-9
5-formyl-2-hydroxy-benzamide

: 636595-43-2
N-(5-{4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxo-imidazolidin-1-yl]but-2-ynyloxymethyl}-2-hydroxybenzamidomethyl)doxorubicin

Guidance literature:: Multi-step reaction with 7 steps

1.1: decaborane / 5 h / 60 °C

2.1: 233 mg / p-TsOH / acetone / 1.5 h / 85 °C

3.1: pyridine; Et₃N / tetrahydrofuran / 1 h / 20 °C

4.1: 162 mg / LiBr / tetrahydrofuran

5.1: NaH / dimethylformamide / 3 h / 20 °C

5.2: 82 percent / dimethylformamide / 6 h / 20 °C

6.1: 80 percent / aq. p-TsOH / methanol / 24 h / 90 °C

7.1: dimethylformamide; H₂O / 0.25 h / 55 °C

7.2: dimethylformamide; H₂O / 0.25 h / 55 °C

With pyridine; Decaborane; sodium hydride; toluene-4-sulfonic acid; triethylamine; lithium bromide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm0303305