CPI-203

Base Information

• Chemical Name: CPI-203
• CAS No.: 1446144-04-2
• Molecular Formula: C19H18ClN5OS
• Molecular Weight: 399.89712
• Mol file: 1446144-04-2.mol

Synonyms:(6S)-4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide;(6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-Thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic amide;(6S)-4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide CPI 203;CPI 203 (6S)-4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide

Chemical Property of CPI-203

Chemical Property:

• Boiling Point: 690.4±65.0 °C(Predicted)
• PKA: 16.00±0.40(Predicted)
• PSA: 114.40000
• Density: 1.51±0.1 g/cm3(Predicted)
• LogP: 3.81080
• Storage Temp.: 2-8°C
• Solubility.: ≥40 mg/mL in DMSO; insoluble in H2O; ≥6.1 mg/mL in EtOH with ultrasonic

Purity/Quality:

98%,99%, ^*data from raw suppliers

CPI-203 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: CPI-203 is a primary amide analog of (+)-JQ1, which has shown superior bioavailability with oral or i.p. administration. CPI-203 downregulates Myc expression, causes G1 cell cycle arrest and attenuates cell proliferation in human pancreatic neuroendocrine tumors. CPI-203 also arrests the growth of T cell acute lymphoblastic leukemia cells in vitro (EC50 = 91.2 nM).
• Uses: CPI-203 is a bromodomain and extraterminal domain (BET) inhibitor.

Technology Process of CPI-203

There total 2 articles about CPI-203 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: 98.5%

(S)-[4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl]acetic acid (202592-23-2) → (S)-2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f ][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetamide (1446144-04-2)

Guidance literature:

With ammonium chloride; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield:

(S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate (1268524-70-4) → (S)-2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f ][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetamide (1446144-04-2)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 1 h / 23 °C

2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; ammonium chloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 23 °C

With ammonium chloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.0c01845

upstream raw materials:

(S)-[4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl]acetic acid

(S)-tert-butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate

Refernces

• 1、 -. "CONJUGATED CHEMICAL INDUCERS OF DEGRADATION AND METHODS OF USE". Page/Page column 505. . Retrieved 2020/05/28.