CZ415

Base Information

• Chemical Name: CZ415
• CAS No.: 1429639-50-8
• Molecular Formula: C₂₂H₂₉N₅O₄S
• Molecular Weight: 459.569
• Mol file: 1429639-50-8.mol

Synonyms:(S)-1-(4-(7,7-dimethyl-4-(3-methylmorpholino)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea

Chemical Property of CZ415

Chemical Property:

• Boiling Point: 611.4±55.0 °C(Predicted)
• PKA: 13.79±0.46(Predicted)
• Density: 1.287±0.06 g/cm3(Predicted)

Purity/Quality:

97% ^*data from raw suppliers

CZ415 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: CZ415 is an inhibitor of mammalian target of rapamycin (mTOR; Kd = 6.3 nM). It is 1,000-fold selective for mTOR over a panel of 285 kinases. CZ415 inhibits phosphorylation of S6 ribosomal protein (S6RP) and Akt in HEK293T cells (IC50s = 14.5 and 14.8 nM, respectively). It inhibits IFN-γ secretion in IL-2, anti-CD3, and anti-CD28 antibody-stimulated human whole blood (IC50 = 226 nM). CZ415 (10 mg/kg) reduces fore paw joint erythema and swelling in a mouse model of collagen-induced arthritis. It also inhibits intratumor mTOR activity and reduces tumor growth in an OCC-1 oral cavity carcinoma mouse xenograft model when administered at a dose of 20 mg/kg.
• Uses: CZ415 is a selective and potent ATP-competitive mTOR inhibitor (1). It demonstrated in vivo efficacy in a semitherapeutic collagen induced arthritis (CIA) mouse model.

Technology Process of CZ415

There total 7 articles about CZ415 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: 31.0%

1-ethyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]urea (874291-00-6) + (S)-2-chloro-7,7-dimethyl-4-(3-methylmorpholino)-5,7-dihydrothieno[3,4-d]pyrimidine 6,6-dioxide (1429639-88-2) → (S)-1-(4-(7,7-dimethyl-4-(3-methylmorpholino)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea (1429639-50-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,2-dimethoxyethane; water; at 70 ℃;

DOI:10.1021/acsmedchemlett.6b00149

Reference yield:

α-Isobuttersaeure-β-propionsaeure-diethylestersulfid (52662-42-7) → (S)-1-(4-(7,7-dimethyl-4-(3-methylmorpholino)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea (1429639-50-8)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium ethanolate / diethyl ether / Reflux

2: sodium carbonate / 40 °C

3: hydrogenchloride; water / acetic acid / Reflux

4: P,P-dichlorophenylphosphine oxide / 135 - 165 °C

5: 3-chloro-benzenecarboperoxoic acid / dichloromethane

6: triethylamine / N,N-dimethyl-formamide / 0 - 20 °C

7: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,2-dimethoxyethane / 70 °C

With P,P-dichlorophenylphosphine oxide; hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; sodium ethanolate; sodium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 7: |Suzuki-Miyaura Coupling;

DOI:10.1021/acsmedchemlett.6b00149

Reference yield:

C10H14N2OS2 → (S)-1-(4-(7,7-dimethyl-4-(3-methylmorpholino)-6,6-dioxido-5,7-dihydrothieno[3,4-d]pyrimidin-2-yl)phenyl)-3-ethylurea (1429639-50-8)

Guidance literature:

Multi-step reaction with 5 steps

1: hydrogenchloride; water / acetic acid / Reflux

2: P,P-dichlorophenylphosphine oxide / 135 - 165 °C

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane

4: triethylamine / N,N-dimethyl-formamide / 0 - 20 °C

5: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,2-dimethoxyethane / 70 °C

With P,P-dichlorophenylphosphine oxide; hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; sodium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In 1,2-dimethoxyethane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 5: |Suzuki-Miyaura Coupling;

DOI:10.1021/acsmedchemlett.6b00149

upstream raw materials:

C₈H₁₀N₂O₂S

C₈H₈Cl₂N₂S

1-ethyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]urea

(S)-2-chloro-7,7-dimethyl-4-(3-methylmorpholino)-5,7-dihydrothieno[3,4-d]pyrimidine 6,6-dioxide