7-[trans-4-(4-Methylpiperazin-1-Yl)cyclohexyl]-5-(4-Phenoxyphenyl)-7h-Pyrrolo[2,3-D]pyrimidin-4-Amine

Base Information

• Chemical Name: 7-[trans-4-(4-Methylpiperazin-1-Yl)cyclohexyl]-5-(4-Phenoxyphenyl)-7h-Pyrrolo[2,3-D]pyrimidin-4-Amine
• CAS No.: 364042-47-7
• Deprecated CAS: 497080-74-7
• Molecular Formula: C₂₉H₃₄N₆O
• Molecular Weight: 482.629
• Nikkaji Number: J1.750.708G,J1.750.712E
• Wikidata: Q27467117,Q27467116
• Pharos Ligand ID: H8A9PRWJ7V1N,H8AN4JBT8FC2,H8APVTYQJQ5Q
• ChEMBL ID: CHEMBL47203,CHEMBL45177,CHEMBL1997617
• Mol file: 364042-47-7.mol

Synonyms:A 419259;A-419259;A419259

Chemical Property of 7-[trans-4-(4-Methylpiperazin-1-Yl)cyclohexyl]-5-(4-Phenoxyphenyl)-7h-Pyrrolo[2,3-D]pyrimidin-4-Amine

Chemical Property:

• Boiling Point: 686.4±55.0 °C(Predicted)
• PKA: 8.20±0.42(Predicted)
• PSA: 72.44000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 8.06690
• Storage Temp.: room temp
• Solubility.: H2O: soluble10mg/mL (clear solution)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 482.27940973
• Heavy Atom Count: 36
• Complexity: 679

Purity/Quality:

97% ^*data from raw suppliers

A 419259 trihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCN(CC1)C2CCC(CC2)N3C=C(C4=C(N=CN=C43)N)C5=CC=C(C=C5)OC6=CC=CC=C6
• Description: A-419259 is an inhibitor of Src family kinases, including Src, LCK, Lyn, and Hck (IC50s = 9, <3, <3, and 11.26 nM, respectively)., It is selective for these kinases over c-Abl (IC50 = 3,000 nM) and PKC (IC50 = >33 μM). A-419259 inhibits growth of Philadelphia chromosome-positive (Ph+) K-562 and Meg-01 myeloid leukemia cells (IC50s = 0.1-0.3 and 0.1 μM, respectively), but not Ph- TF-1 and HEL cells. It induces apoptosis in K-562 cells in a concentration-dependent manner. A-419259 (300 nM) inhibits differentiation of murine embryonic stem cells while maintaining pluripotency. It reduces the total number of acute myeloid leukemia (AML) cells, as well as AML stem cells, in the bone marrow and spleen in mouse patient-derived xenograft (PDX) models of AML when administered at a dose of 30 mg/kg twice daily.
• Uses: A 419259 Trihydrochloride is the hydrochloride form of A 419259 which is a Src kinase inhibitor and can be used in treatment of chronic myelogenous leukemia, lymphangioleiomyomatosis and tuberous sclerosis.

Technology Process of 7-[trans-4-(4-Methylpiperazin-1-Yl)cyclohexyl]-5-(4-Phenoxyphenyl)-7h-Pyrrolo[2,3-D]pyrimidin-4-Amine

There total 22 articles about 7-[trans-4-(4-Methylpiperazin-1-Yl)cyclohexyl]-5-(4-Phenoxyphenyl)-7h-Pyrrolo[2,3-D]pyrimidin-4-Amine 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: 16.5%

1-methyl-piperazine (109-01-3) + 4-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexan-1-one (262433-52-3) → 7-((1R,4R)-4-(4-methylpiperazin-1-yl)cyclohexyl)-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (364042-47-7) + 7-((cis)-4-(4-methylpiperazin-1-yl)cyclohexyl)-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (364042-47-7)

Guidance literature:

1-methyl-piperazine; 4-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexan-1-one; With acetic acid; In 1,2-dichloro-ethane; at 20 ℃; for 5h; Molecular sieve;

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 16h;

Reference yield: 16.5%

1-methyl-piperazine (109-01-3) + 4-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexan-1-one (262433-52-3) → 7-((1R,4R)-4-(4-methylpiperazin-1-yl)cyclohexyl)-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (364042-47-7) + 7-((cis)-4-(4-methylpiperazin-1-yl)cyclohexyl)-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (364042-47-7)

Guidance literature:

1-methyl-piperazine; 4-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexan-1-one; With acetic acid; In 1,2-dichloro-ethane; at 20 ℃; for 5h; Molecular sieve;

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 16h;

Reference yield:

4,4-ethylenedioxycyclohexan-1-ol (22428-87-1) → 7-((1R,4R)-4-(4-methylpiperazin-1-yl)cyclohexyl)-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (364042-47-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / Ph₃P; DEAD / tetrahydrofuran

2: 75 percent / Pd(PPh₃)4; Na₂CO₃ / 1,2-dimethoxy-ethane; H₂O

3: 80 percent / NH₄OH / dioxane / 120 °C / Parr pressure vessel

4: 92 percent / aq. HCl / acetone

5: Na(OAc)3BH; AcOH / acetone; 1,2-dichloro-ethane

With hydrogenchloride; ammonium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium tris(acetoxy)borohydride; sodium carbonate; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; water; 1,2-dichloro-ethane; acetone; 1: Mitsunobu coupling / 2: Suzuki coupling;

DOI:10.1016/S0960-894X(02)00195-6

upstream raw materials:

1-methyl-piperazine

4-(4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclohexan-1-one

4,4-ethylenedioxycyclohexan-1-ol

4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine