(R)-(-)-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: (R)-(-)-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.: 1268524-71-5
• Molecular Formula: C23H25ClN4O2S
• Molecular Weight: 456.996
• Mol file: 1268524-71-5.mol

Synonyms:(R)-(-)-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 (R)-(-)-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(Predicted)
• PKA: 2.05±0.60(Predicted)
• PSA: 97.61000
• Density: 1.33
• LogP: 4.96690
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble20mg/mL, clear

Purity/Quality:

97% ^*data from raw suppliers

(-)-JQ1 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: The bromodomain and extra terminal domain (BET) family of proteins, including BRD2, BRD3, and BRD4, play a key role in many cellular processes, including inflammatory gene expression, mitosis, and viral/host interaction by controlling the assembly of histone acetylation-dependent chromatin complexes. (±)-JQ1 displaces BET proteins from chromatin by competitively binding to the acetyl-lysine recognition pocket of BET bromodomains. The (?)-JQ1 stereoisomer has no appreciable affinity to BET bromodomains, whereas enantiomerically pure (+)-JQ1 binds to BRD4 bromodomains 1 and 2 with Kd values of ~50 and 90 nM, respectively.
• Uses: (R)-(-)-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 is the enantiomer 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 (T117580), which is BET bromodomain inhibitor, also activates HIV latency through antagonizing Brd4 inhibition of Tat-transactivation.

Technology Process of (R)-(-)-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 10 articles about (R)-(-)-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:

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

Reference yield:

(2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone (50508-66-2) → (-)-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:

[4-(4-chlorophenyl)-2,3,9-trimethyl-6H-1-thia-5,7,8,9a-tetraazacyclopenta[e]azulen-6-yl]acetic acid tert-butyl ester

acetic acid hydrazide

Fmoc-(tBu)Asp-OH

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

Downstream raw materials:

C₁₉H₁₉ClN₆OS

(R)-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)acetic acid