CEP-28122

Base Information

• Chemical Name: CEP-28122
• CAS No.: 1022958-60-6
• Molecular Formula: C₂₈H₃₅ClN₆O₃
• Molecular Weight: 539.077
• Mol file: 1022958-60-6.mol

Synonyms:CEP-28122;(1S,2S,3R,4R)-3-[[5-Chloro-2-[[(7S)-6,7,8,9-tetrahydro-1-methoxy-7-(4-morpholinyl)-5H-benzocyclohepten-2-yl]amino]-4-pyrimidinyl]amino]-bicyclo[2.2.1]hept-5-ene-2-carboxamide

Chemical Property of CEP-28122

Chemical Property:

• Boiling Point: 786.9±70.0 °C(Predicted)
• PKA: 16.24±0.40(Predicted)
• PSA: 114.63000
• Density: 1.357±0.06 g/cm3(Predicted)
• LogP: 4.33390
• Solubility.: ≤30mg/ml in DMSO;12mg/ml in dimethyl formamide

Purity/Quality:

97% ^*data from raw suppliers

CEP-28122 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: CEP-28122 is used as an orally efficacious inhibitor of (ALK), analplastic lymphoma kinase, in the treatment of cancer.

Technology Process of CEP-28122

There total 22 articles about CEP-28122 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: 39.0%

(1S,2S,3R,4R)-3-(2,5-dichloro-pyrimidin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (1022961-42-7) + 1-methoxy-7-(morphoin-4-yl)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-2-ylamine (1022951-69-4) → CEP-28122 (1022958-60-6)

Guidance literature:

With hydrogenchloride; In 2-methoxy-ethanol; at 110 ℃;

DOI:10.1021/op200313v

Reference yield: 33.0%

(1S,2S,3R,4R)-3-(2,5-dichloro-pyrimidin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (1022961-42-7) + 1-methoxy-7-(morphoin-4-yl)-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-2-ylamine (1022951-69-4) → CEP-28122 (1022958-60-6) + (1S,2S,3R,4R)-3-[5-chloro-2-((R)-1-methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-2-ylamino)pyrimidin-4-ylamino]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (1022958-53-7)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; isopropyl alcohol; at 140 ℃; for 0.833333h; Microwave irradiation;

DOI:10.1021/jm201550q

Reference yield:

2,3-dimethylanisole (2944-49-2) → CEP-28122 (1022958-60-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: aluminum (III) chloride; sulfuryl dichloride / chlorobenzene / 22 h / 13 - 20 °C / Large scale reaction

2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chlorobenzene / 2.5 h / 90 - 100 °C / Large scale reaction

3.1: sodium hydrogencarbonate

4.1: potassium nitrate; trifluoroacetic acid / -10 - 36 °C / Large scale reaction

5.1: formic acid / methanol / 0.17 h / 15 - 40 °C / Large scale reaction

5.2: 1.5 h / 65 °C / Large scale reaction

6.1: hydrogenchloride / 2-methoxy-ethanol / 110 °C

With hydrogenchloride; aluminum (III) chloride; N-Bromosuccinimide; formic acid; sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); sodium hydrogencarbonate; potassium nitrate; trifluoroacetic acid; In methanol; 2-methoxy-ethanol; chlorobenzene;

DOI:10.1021/op200313v

upstream raw materials:

(1S,2S,3R,4R)-3-exo-N-^tbutyloxycarbonylaminobicyclo[2,2,1]hept-5-ene-2-exo-carboxylic acid

((1R,2R,3S,4S)-3-carbamoyl-bicyclo[2.2.1]hept-5-en-2-yl)-carbamic acid tert-butyl ester

(1SR,2SR,5RS,6RS)-4-oxo-3-aza-tricyclo[4.2.1.0(2,5)]non-7-ene-3-carboxylic acid tert-butyl ester

(1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide trifluoroacetate salt