6-methoxy-4-(4-methylpiperazin-1-yl)-N₁-(4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Base Information

• Chemical Name: 6-methoxy-4-(4-methylpiperazin-1-yl)-N₁-(4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
• CAS No.: 1421372-35-1
• Molecular Formula: C₂₃H₂₆N₈O
• Molecular Weight: 430.512

Synonyms:6-methoxy-4-(4-methylpiperazin-1-yl)-N₁-(4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Chemical Property of 6-methoxy-4-(4-methylpiperazin-1-yl)-N₁-(4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

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Technology Process of 6-methoxy-4-(4-methylpiperazin-1-yl)-N₁-(4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

There total 15 articles about 6-methoxy-4-(4-methylpiperazin-1-yl)-N₁-(4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine 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: 75.0%

N-(2-methoxy-4-(4-methylpiperazin-1-yl)-5-nitrophenyl)-4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine (1453199-61-5) → 6-methoxy-4-(4-methylpiperazin-1-yl)-N1-(4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (1421372-35-1)

Guidance literature:

With iron; ammonium chloride; In ethanol; water; for 1.5h; Reflux;

DOI:10.1021/jm400822z

Reference yield: 53.0%

[(Z)-3-(dimethylamino)-3-pyrazolo[1,5-a]pyridin-3-yl-prop-2-enylidene]-dimethyl-ammonium hexafluorophosphate (1421372-37-3) + 1-[5-amino-2-methoxy-4-(4-methylpiperazin-1-yl)phenyl]guanidine (1421372-40-8) → 6-methoxy-4-(4-methylpiperazin-1-yl)-N1-(4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (1421372-35-1)

Guidance literature:

With N,N,N',N'-tetramethylguanidine; In 2-methoxy-ethanol; at 120 - 140 ℃; for 0.75h; Inert atmosphere; Sealed tube; Microwave irradiation;

Reference yield:

2-methoxy-4-(4-methylpiperazin-1-yl)-5-nitroaniline (1421372-03-3) → 6-methoxy-4-(4-methylpiperazin-1-yl)-N1-(4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine (1421372-35-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: methanesulfonic acid / water; butan-1-ol / 1 h / 90 °C

2.1: hydrogen; palladium 10% on activated carbon / ethanol / 18 h / 20 °C

2.2: 2 h / 20 °C

3.1: N,N,N',N'-tetramethylguanidine / 2-methoxy-ethanol / 0.75 h / 120 - 140 °C / Inert atmosphere; Sealed tube; Microwave irradiation

With methanesulfonic acid; palladium 10% on activated carbon; hydrogen; N,N,N',N'-tetramethylguanidine; In ethanol; 2-methoxy-ethanol; water; butan-1-ol;

upstream raw materials:

2-methoxy-4-(4-methylpiperazin-1-yl)-5-nitroaniline

(2-methoxy-4-(4-methylpiperazin-1-yl)-5-nitrophenyl)carbamic acid tert-butyl ester

2-methoxy-4-(4-methylpiperazin-1-yl)-5-nitrobenzoic acid

[(Z)-3-(dimethylamino)-3-pyrazolo[1,5-a]pyridin-3-yl-prop-2-enylidene]-dimethyl-ammonium hexafluorophosphate

Downstream raw materials:

N-(4-methoxy-2-(4-methylpiperazin-1-yl)-5-(4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-ylamino)phenyl)acrylamide

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