Sograzepide

Base Information

• Chemical Name: Sograzepide
• CAS No.: 155488-25-8
• Molecular Formula: C28H30N6O3
• Molecular Weight: 498.585
• UNII: HOU4I0G29C
• DSSTox Substance ID: DTXSID00165906
• Nikkaji Number: J806.697C
• Wikidata: Q2297773
• NCI Thesaurus Code: C87692
• Pharos Ligand ID: RQJ5C59USGR6
• Metabolomics Workbench ID: 153356
• ChEMBL ID: CHEMBL324547
• Mol file: 155488-25-8.mol

Synonyms:N-(1-(tert-butylcarbonylmethyl)-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4-benzodiazepin-3-yl)-N'-(3-(methylamino)phenyl)urea;netazepide;YF 476;YF-476;YF476

Chemical Property of Sograzepide

Chemical Property:

• Boiling Point: 723.049 °C at 760 mmHg
• PKA: 11.38±0.40(Predicted)
• Flash Point: 391.086 °C
• PSA: 119.28000
• Density: 1.257 g/cm³
• LogP: 4.04840
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 498.23793884
• Heavy Atom Count: 37
• Complexity: 869

Purity/Quality:

99% ^*data from raw suppliers

Sograzepide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)CN1C2=CC=CC=C2C(=NC(C1=O)NC(=O)NC3=CC=CC(=C3)NC)C4=CC=CC=N4
• Isomeric SMILES: CC(C)(C)C(=O)CN1C2=CC=CC=C2C(=N[C@H](C1=O)NC(=O)NC3=CC=CC(=C3)NC)C4=CC=CC=N4
• Recent ClinicalTrials: Trial of a Gastrin Receptor Antagonist in Barrett's Esophagus
• Recent EU Clinical Trials: Randomized, placebo-controlled trial of YF476, a gastrin receptor antagonist, in Barrett’s esophagus (10-505; T-016)
• Uses: Sograzepide is used in the treatment of gastric carcinoids or patients with chronic atrophic gastritis. Gastric receptor antagonist.

Technology Process of Sograzepide

There total 14 articles about Sograzepide 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:

(3-{3-[(R)-1-(3,3-Dimethyl-2-oxo-butyl)-2-oxo-5-pyridin-2-yl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl]-ureido}-phenyl)-methyl-carbamic acid tert-butyl ester → N-((3R)-1-tert-Butylcarbonylmethyl-2,3-dihydro-2-oxo-5-(pyridin-2-yl)-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylaminophenyl)urea (155488-25-8)

Guidance literature:

With hydrogenchloride; In ethyl acetate; for 3h; Yield given;

DOI:10.1021/jm960669+

Reference yield:

2-(2-aminobenzoyl)pyridine (42471-56-7) → N-((3R)-1-tert-Butylcarbonylmethyl-2,3-dihydro-2-oxo-5-(pyridin-2-yl)-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylaminophenyl)urea (155488-25-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / EDC, DMAP / CH₂Cl₂ / 0.33 h / 0 - 20 °C

2: sat. NH₃ in MeOH / 1 h / Ambient temperature

3: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 1 h

4: 93 percent / gas. HBr / CH₂Cl₂ / 4 h / 0 °C

6: CH₂Cl₂ / 0.5 h / Ambient temperature

7: aq. HCl / ethyl acetate / 3 h

With hydrogenchloride; dmap; ammonia; hydrogen bromide; sodium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; ethyl acetate;

DOI:10.1021/jm960669+

Reference yield:

meta-aminobenzoic acid (99-05-8,159139-79-4) → N-((3R)-1-tert-Butylcarbonylmethyl-2,3-dihydro-2-oxo-5-(pyridin-2-yl)-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylaminophenyl)urea (155488-25-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 91 percent / 2M aq. KOH / dioxane / Ambient temperature

2: 1.) NaH / 1.) DMF, from 10 deg C to RT, 1 h, 2.) DMF, RT, 2 h

3: acetone / 0.5 h

4: aq. NaN₃ / acetone / 1 h

5: toluene / 2 h / Heating

6: CH₂Cl₂ / 0.5 h / Ambient temperature

7: aq. HCl / ethyl acetate / 3 h

With hydrogenchloride; potassium hydroxide; sodium azide; sodium hydride; In 1,4-dioxane; dichloromethane; ethyl acetate; acetone; toluene;

DOI:10.1021/jm960669+

upstream raw materials:

2-(2-aminobenzoyl)pyridine

meta-aminobenzoic acid

3-[(tert-butoxycarbonyl)amino]benzoic acid

1,3-dihydro-5-(pyridin-2-yl)-3(R,S)-[(benzyloxycarbonyl)-amino]-2H-1,4-benzodiazepin-2-one

Refernces

• 1、 -. "Benzodiazepine derivatives useful as CCK-receptor antagonists". . . Retrieved 2008/06/13.