SGC-CBP30

Base Information

• Chemical Name: SGC-CBP30
• CAS No.: 1613695-14-9
• Molecular Formula: C28H33ClN4O3
• Molecular Weight: 509.048
• Mol file: 1613695-14-9.mol

Synonyms:SGC-CBP30;2-[2-(3-Chloro-4-methoxyphenyl)ethyl]-5-(dimethyl-1,2-oxazol-4-yl)-1-[(2S)-2-(morpholin-4-yl)propyl]-1H-1,3-benzodiazole;2-[2-(3-chloro-4-methoxyphenyl)ethyl]-5-(3,5-dimethyl-4-isoxazolyl)-1-[(2S)-2-(4-morpholinyl)propyl]-1H-benzimidazole SGC-CBP30;2-[2-(3-Chloro-4-methoxyphenyl)ethyl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(S)-2-(morpholin-4-yl)propyl]-1H-benzimidazole;2-[2-(3-Chloro-4-methoxyphenyl)ethyl]-5-(3,5-dimethyl-4-isoxazolyl)-1-[(2S)-2-(4-morpholinyl)propyl]-1H-benzimidazole

Chemical Property of SGC-CBP30

Chemical Property:

• Boiling Point: 678.0±55.0 °C(Predicted)
• PKA: 6.98±0.10(Predicted)
• PSA: 65.55000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 5.41390
• Storage Temp.: 2-8°C
• Solubility.: ≥20.05 mg/mL in DMSO; ≥25.7 mg/mL in EtOH with ultrasonic; ≥4.67 mg/mL in H2O with ultrasonic

Purity/Quality:

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

SGC-CBP30 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: SGC-CBP30 is a potent CBP/p300 bromodomain (BRD) inhibitor. SGC-CBP30 shows Kd values are 21 and 32 nM for CBP and p300 BRDs respectively. SGC-CBP30 also exhibits 40-fold and 250-fold selectivity for CBP over the first BRD of BRD4 (BRD4(1)) and BRD4(2) respectively. SGC-CBP30 accelerates FRAP recovery in cells at a concentration of 1 ?M.
• Uses: SGC-CBP30 is a potent CREBBP/EP300 inhibitor.

Technology Process of SGC-CBP30

There total 6 articles about SGC-CBP30 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: 52.0%

3-(3-chloro-4-methoxyphenyl)propionic acid (1857-56-3) + C18H26N4O2 → 2-[2-(3-chloro-4-methoxyphenyl)ethyl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(2S)-2-(morpholin-4-yl)propyl]-1H-benzimidazole (1613695-14-9)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 80 ℃; for 16h;

DOI:10.1021/ja412434f

Reference yield:

4-Bromo-1-fluoro-2-nitrobenzene (364-73-8) → 2-[2-(3-chloro-4-methoxyphenyl)ethyl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(2S)-2-(morpholin-4-yl)propyl]-1H-benzimidazole (1613695-14-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); sodium hydrogencarbonate / 1,2-dimethoxyethane / 3 h / 80 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C

2.2: 4 h / Reflux

3.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C

4.1: sodium dithionite / ethanol / 1 h / 80 °C

5.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 16 h / 80 °C

With sodium dithionite; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); sodium hydrogencarbonate; potassium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; ethyl acetate; N,N-dimethyl-formamide; 1.1: |Suzuki Coupling;

DOI:10.1021/ja412434f

Reference yield:

3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole (832114-00-8) → 2-[2-(3-chloro-4-methoxyphenyl)ethyl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(2S)-2-(morpholin-4-yl)propyl]-1H-benzimidazole (1613695-14-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); sodium hydrogencarbonate / 1,2-dimethoxyethane / 3 h / 80 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / 20 °C

2.2: 4 h / Reflux

3.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C

4.1: sodium dithionite / ethanol / 1 h / 80 °C

5.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 16 h / 80 °C

With sodium dithionite; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); sodium hydrogencarbonate; potassium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; ethyl acetate; N,N-dimethyl-formamide; 1.1: |Suzuki Coupling;

DOI:10.1021/ja412434f

upstream raw materials:

4-Bromo-1-fluoro-2-nitrobenzene

3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole

4-(4-fluoro-3-nitrophenyl)-3,5-dimethyl-1,2-oxazole

3-(3-chloro-4-methoxyphenyl)propionic acid

Refernces