6-bromo-3-(1-methyl-1H-pyrazol-4-yl)-5-(piperidin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine

Base Information

• Chemical Name: 6-bromo-3-(1-methyl-1H-pyrazol-4-yl)-5-(piperidin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine
• CAS No.: 891494-63-6
• Molecular Formula: C₁₅H₁₈BrN₇
• Molecular Weight: 376.259
• European Community (EC) Number: 686-168-1
• ChEMBL ID: CHEMBL1643208
• Metabolomics Workbench ID: 152980
• Nikkaji Number: J3.517.083I
• Pharos Ligand ID: HV222U94S2R7
• Wikidata: Q27086899
• Mol file: 891494-63-6.mol

Synonyms:MK-8776;MK8776;Sch 900776;Sch-900776;Sch900776

Chemical Property of 6-bromo-3-(1-methyl-1H-pyrazol-4-yl)-5-(piperidin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine

Chemical Property:

• PKA: 8.88±0.10(Predicted)
• PSA: 86.06000
• Density: 1.80
• LogP: 2.85150
• Solubility.: insoluble in H2O; insoluble in EtOH; ≥18.8 mg/mL in DMSO
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 375.08071
• Heavy Atom Count: 23
• Complexity: 425

Purity/Quality:

97% ^*data from raw suppliers

6-Bromo-3-(1-methyl-1H-pyrazol-4-yl)-5-(3R)-3-piperidinylpyrazolo[1,5-a]pyrimidin-7-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C=N1)C2=C3N=C(C(=C(N3N=C2)N)Br)C4CCCNC4
• Recent ClinicalTrials: A Dose-escalation Study of MK-8776 (SCH 900776) With and Without Gemcitabine in Participants With Solid Tumors or Lymphoma (MK-8776-002/P05248)
• Uses: SCH900776 acts as a novel Chk1 inhibitor acting as an anticancer agent.

Technology Process of 6-bromo-3-(1-methyl-1H-pyrazol-4-yl)-5-(piperidin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine

There total 12 articles about 6-bromo-3-(1-methyl-1H-pyrazol-4-yl)-5-(piperidin-3-yl)pyrazolo[1,5-a]pyrimidin-7-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: 90.0%

C20H26BrN7O2 (1335211-24-9) → MK-8776 (891494-63-6,891494-64-7)

Guidance literature:

C₂₀H₂₆BrN₇O₂; With hydrogenchloride; In ethanol; water; at 50 ℃; for 1.5h;

With potassium hydroxide; In ethanol; water; at 5 - 78 ℃; pH=5 - 11; Cooling;

Reference yield:

(R)-1-Boc-nipecotic acid (163438-09-3) → MK-8776 (891494-63-6,891494-64-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrahydrofuran / 18 h / 25 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

2.2: 0.67 h / -78 °C

3.1: ethanol / 18 h / 45 °C

4.1: N-Bromosuccinimide / dichloromethane; acetonitrile

5.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

5.2: 4 h / 20 °C

With N-Bromosuccinimide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

Reference yield:

C14H21N3O3 → MK-8776 (891494-63-6,891494-64-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

1.2: 0.67 h / -78 °C

2.1: ethanol / 18 h / 45 °C

3.1: N-Bromosuccinimide / dichloromethane; acetonitrile

4.1: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

4.2: 4 h / 20 °C

With N-Bromosuccinimide; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

upstream raw materials:

C₂₀H₂₆BrN₇O₂

1-methylpyrazole-4-carbaldehyde

(1-methyl-1H-pyrazol-4-yl)acetonitrile

C₇H₇N₃O