(R)-1-(methyl(1-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido-[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridazin-3-yl)piperidin-4-yl)amino)propan-2-ol

Base Information

• Chemical Name: (R)-1-(methyl(1-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido-[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridazin-3-yl)piperidin-4-yl)amino)propan-2-ol
• CAS No.: 1588958-96-6
• Molecular Formula: C₂₉H₃₉N₉O
• Molecular Weight: 529.688
• Mol file: 1588958-96-6.mol

Synonyms:

Chemical Property of (R)-1-(methyl(1-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido-[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridazin-3-yl)piperidin-4-yl)amino)propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-(methyl(1-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido-[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridazin-3-yl)piperidin-4-yl)amino)propan-2-ol

There total 12 articles about (R)-1-(methyl(1-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido-[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridazin-3-yl)piperidin-4-yl)amino)propan-2-ol 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:

trans-4-methylcyclohexylamine hydrochloride (33483-65-7) → (R)-1-(methyl(1-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido-[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridazin-3-yl)piperidin-4-yl)amino)propan-2-ol (1588958-96-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine / butan-1-ol / 36 h / Reflux; Inert atmosphere

2.1: N-iodo-succinimide / N,N-dimethyl-formamide / 2.16 h / 10 - 20 °C / Inert atmosphere

3.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 2.25 h / -74 - 0 °C / Inert atmosphere

3.2: 0.58 h / -60 °C / Inert atmosphere

3.3: Reflux; Inert atmosphere

4.1: lithium hexamethyldisilazane / 1-methyl-pyrrolidin-2-one / 90 °C / Inert atmosphere

5.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / 1,4-dioxane / Inert atmosphere

6.1: hydrogenchloride / water / Inert atmosphere

7.1: ammonium acetate / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere

7.2: 2 h / 60 °C / Inert atmosphere

8.1: formic acid; sodium tris(acetoxy)borohydride / water; dichloromethane / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-iodo-succinimide; n-butyllithium; formic acid; ammonium acetate; sodium tris(acetoxy)borohydride; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium hexamethyldisilazane; sodium t-butanolate; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; hexane; dichloromethane; water; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1021/jm500118j

Reference yield:

C27H32N8O2 → (R)-1-(methyl(1-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido-[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridazin-3-yl)piperidin-4-yl)amino)propan-2-ol (1588958-96-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / water / Inert atmosphere

2.1: ammonium acetate / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 2 h / 60 °C / Inert atmosphere

3.1: formic acid; sodium tris(acetoxy)borohydride / water; dichloromethane / Inert atmosphere

With hydrogenchloride; formic acid; ammonium acetate; sodium tris(acetoxy)borohydride; In dichloromethane; water;

DOI:10.1021/jm500118j

Reference yield:

trans-4-methylcyclohexanamine (2523-55-9) → (R)-1-(methyl(1-(6-((9-((1r,4r)-4-methylcyclohexyl)-9H-pyrido-[4′,3′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridazin-3-yl)piperidin-4-yl)amino)propan-2-ol (1588958-96-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1,4-dioxane / Inert atmosphere; Reflux

2.1: ammonium hydroxide / isopropyl alcohol / 120 °C / Inert atmosphere

3.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 1,4-dioxane / 120 - 150 °C / Inert atmosphere; Sealed tube

4.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / 1,4-dioxane / 150 °C / Inert atmosphere; Microwave irradiation

5.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate / 1,4-dioxane / Inert atmosphere

6.1: hydrogenchloride / water / Inert atmosphere

7.1: ammonium acetate / 0.33 h / 20 °C / Molecular sieve; Inert atmosphere

7.2: 2 h / 60 °C / Inert atmosphere

8.1: formic acid; sodium tris(acetoxy)borohydride / water; dichloromethane / Inert atmosphere

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; ammonium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; formic acid; ammonium acetate; sodium tris(acetoxy)borohydride; sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; dichloromethane; water; isopropyl alcohol; 3.1: |Suzuki Coupling / 4.1: |Buchwald-Hartwig Coupling;

DOI:10.1021/jm500118j

upstream raw materials:

trans-4-methylcyclohexylamine hydrochloride

(2R)-hydroxypropylamine

trans-4-methylcyclohexanamine

C₁₁H₁₅BrClN₃