Unii-24P4O1J71F

Base Information

• Chemical Name: Unii-24P4O1J71F
• CAS No.: 688756-00-5
• Molecular Formula: C₂₃H₂₀Cl₂F₃N₅O₅S
• Molecular Weight: 606.41
• UNII: 24P4O1J71F
• Wikidata: Q27253866
• Mol file: 688756-00-5.mol

Synonyms:BIRT-2584;UNII-24P4O1J71F;24P4O1J71F;BIRT 2584;688756-00-5;BIRT2584;SCHEMBL4017930;Q27253866;(S)-2-[(R)-7-(3,5-Dichloro-phenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxy-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonylamino]-propionamide;PROPANAMIDE, 2-((((3R)-1-(3,5-DICHLOROPHENYL)-2,3-DIHYDRO-3-METHYL-2-OXO-3-((4-(TRIFLUOROMETHOXY)PHENYL)METHYL)-1H-IMIDAZO(1,2-A)IMIDAZOL-5-YL)SULFONYL)AMINO)-, (2S)-

Chemical Property of Unii-24P4O1J71F

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 605.0514298
• Heavy Atom Count: 39
• Complexity: 1030

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C(=O)N)NS(=O)(=O)C1=CN=C2N1C(C(=O)N2C3=CC(=CC(=C3)Cl)Cl)(C)CC4=CC=C(C=C4)OC(F)(F)F
• Isomeric SMILES: C[C@@H](C(=O)N)NS(=O)(=O)C1=CN=C2N1[C@](C(=O)N2C3=CC(=CC(=C3)Cl)Cl)(C)CC4=CC=C(C=C4)OC(F)(F)F
• Recent EU Clinical Trials: One year follow-up of patients treated in Study 1206.5, a 12 week double-blind, randomised, placebo-controlled, modified dose-escalation trial to investigate safety, efficacy, and pharmacokinetics of BIRT 2584XX tablets at doses of 100,300 and 500 mg administered once daily in patients with moderate to severe psoriasis with a 12 week treatment extension for PASI 50 responders.

Technology Process of Unii-24P4O1J71F

There total 13 articles about Unii-24P4O1J71F 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: 81.0%

(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxy-benzyl)-6,7-dihydro-5H-imidazo[1, 2-a]imidazole-3-sulfonyl chloride (688756-19-6) + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-[(R)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxybenzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazol-3-ylsulfonylamino]propionamide (688756-00-5)

Guidance literature:

With triethylamine; In DMF (N,N-dimethyl-formamide); dichloromethane; at 20 ℃; for 5h;

Reference yield:

(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxy-benzyl)-6,7-dihydro-5H-imidazo[1, 2-a]imidazole-3-sulfonyl chloride (688756-19-6) + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-[(R)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxybenzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazol-3-ylsulfonylamino]propionamide (688756-00-5) + (R)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxybenzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonic acid

Guidance literature:

With water; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 6h;

DOI:10.1021/ol101960x

Reference yield:

C7H8O3S*C9H10Cl2N2O → (S)-2-[(R)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxybenzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazol-3-ylsulfonylamino]propionamide (688756-00-5) + (R)-7-(3,5-dichlorophenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxybenzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonic acid

Guidance literature:

Multi-step reaction with 9 steps

1.1: water; sodium hydroxide / ethyl acetate / 0.5 h

1.2: 10.5 h / 17 - 23 °C / Reflux

1.3: 12 h / 50 °C

2.1: 3 h / 0 - 20 °C

3.1: 1.5 h / 0 - 5 °C

4.1: potassium hydroxide / isopropyl alcohol / 1 h / 60 °C

4.2: 3 h / 60 °C

5.1: 3 h / 60 °C

6.1: 2.5 h / 10 - 20 °C

6.2: 2 h / 40 - 50 °C

7.1: 1.5 h / 10 - 20 °C

8.1: 0.92 h / -15 - -5 °C

8.2: 0.75 h / -15 - -5 °C

8.3: 0.67 h / -5 °C

9.1: 6 h / -20 - 23 °C

With water; potassium hydroxide; sodium hydroxide; In ethyl acetate; isopropyl alcohol;

DOI:10.1021/op200175t

upstream raw materials:

(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-trifluoromethoxy-benzyl)-6,7-dihydro-5H-imidazo[1, 2-a]imidazole-3-sulfonyl chloride

(S)-alaninamide hydrochloride

(2R,5R)-5-(4-trifluoromethoxybenzyl)-3-(3,5-dichlorophenyl)-2-isopropyl-5-methyl-1-(2,2,2-trifluoroacetyl)-imidazolidin-4-one

(R)-2-amino-3-(4-trifluoromethoxyphenyl)-N-(3,5-dichlorophenyl)-2-methylpropionamide p-toluenesulfonic acid salt