(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

Base Information

• Chemical Name: (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
• CAS No.: 1268524-70-4
• Molecular Formula: C23H25ClN4O2S
• Molecular Weight: 456.996
• Mol file: 1268524-70-4.mol

Synonyms:(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;

Chemical Property of (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

Chemical Property:

• Boiling Point: 610.4±65.0 °C at 760 mmHg
• PKA: 2.05±0.60(Predicted)
• Flash Point: 322.9±34.3 °C
• PSA: 97.61000
• Density: 1.3±0.1 g/cm³
• LogP: 4.96690
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble20mg/mL, clear

Purity/Quality:

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

(S)-(+)-Tert-butyl2-(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 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: JQ1 (+) (1268524-70-4) is a potent BET bromodomain inhibitor and is the active isomer.?? IC50 = 17.7, 32.6, 76.9 and 12942 nM respectively for BRD2 (N-terminal (N)), BRD4 (C-terminal (C)), BRD4 (N) and CREBBP respectively (data for + isomer).1 Competitive binding by JQ1 displaces the BRD4 fusion oncoprotein from chromatin, prompting squamous differentiation and specific antiproliferative effects in BRD4-dependent cell lines and patient-derived xenograft models.1?Induces squamous differentiation in NMC cell lines and inhibits tumor growth in NMC xenografts.2?Displays reversible contraceptive effects in male mice.3?Blocks inflammation and bone loss in periodontitis.4?Reverses CAR T cell extinction.5
• Uses: BET bromodomain inhibitor JQ1 activates HIV latency through antagonizing Brd4 inhibition of Tat-transactivation. (+)-JQ1 has been used in flow cytometry assay, cell viability assay and quantitative PCR assay in order to investigate on the reversal of HIV-1 latency.

Technology Process of (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

There total 49 articles about (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 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: 83.0%

ethanol (64-17-5) + acetone (67-64-1) → 2,2-diethoxypropane (126-84-1)

Guidance literature:

With hydrogenchloride; In diethyl ether; at 20 ℃; for 0.333333h;

Reference yield:

C33H32ClN2O6PS + acetic acid hydrazide (1068-57-1) → (-)-JQ1 (1268524-71-5) + (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)

Guidance literature:

In tetrahydrofuran; butan-1-ol; at 20 - 90 ℃; for 2h; Overall yield = 3.04 g;

DOI:10.1016/j.tetlet.2015.02.062

Reference yield:

Fmoc-(tBu)Asp-OH (71989-14-5) → (-)-JQ1 (1268524-71-5) + (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)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 23 °C

2.1: piperidine / N,N-dimethyl-formamide / 23 °C

2.2: 90 °C

3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / -78 - -10 °C

3.2: 0.75 h / -78 - -10 °C

4.1: tetrahydrofuran; butan-1-ol / 2 h / 20 - 90 °C

With piperidine; potassium tert-butylate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1016/j.tetlet.2015.02.062

upstream raw materials:

tert-butyl (S)-2-(5-(4-chlorophenyl)-6,7-dimethyl-2-oxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-3-yl)acetate

acetic acid hydrazide

(2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone

p-chlorobenzoylacetonitrile

Refernces

• 1、 Dong, Guoqiang,He, Shipeng,Li, Yu,Sheng, Chunquan,Wang, Wei,Wu, Shanchao. "Potent Dual BET/HDAC Inhibitors for Efficient Treatment of Pancreatic Cancer". . p. 3028 - 3032. Retrieved 2020/02/11.
• 2、 -. "PROCESS FOR THE MANUFACTURE OF DIAZEPINE DERIVATIVES". . . Retrieved 2018/07/05.