JNJ-18038683 free base

Base Information

• Chemical Name: JNJ-18038683 free base
• CAS No.: 851373-91-6
• Molecular Formula: C20H20ClN3
• Molecular Weight: 337.852
• UNII: 28PGH5X4OQ
• DSSTox Substance ID: DTXSID001336543
• Nikkaji Number: J3.470.858D
• Wikidata: Q27890368
• Pharos Ligand ID: X7H6DHZ1W195
• ChEMBL ID: CHEMBL4205783
• Mol file: 851373-91-6.mol

Synonyms:JNJ-18038683 free base;851373-91-6;UNII-28PGH5X4OQ;28PGH5X4OQ;3-(4-chlorophenyl)-1-(phenylmethyl)-5,6,7,8-tetrahydro-4H-pyrazolo[5,4-d]azepine;3-(4-Chlorophenyl)-1,4,5,6,7,8-hexahydro-1-(phenylmethyl)pyrazolo[3,4-d]azepine;D0T8KA;GTPL8432;SCHEMBL2076477;CHEMBL4205783;TQP0830;UKJPMZGILXATGT-UHFFFAOYSA-N;DTXSID001336543;BDBM50458523;SB18884;5-HT 7 antagonist (depression), Johnson & Johnson;Q27890368;Serotonin 7 antagonist (depression), Johnson & Johnson;1-benzyl-3-(4-chlorophenyl)-1,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine;1-Benzyl-3-(4-chloro-phenyl)-1,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene;1-benzyl-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4H-pyrazolo[3,4-d]azepine;PYRAZOLO(3,4-D)AZEPINE, 3-(4-CHLOROPHENYL)-1,4,5,6,7,8-HEXAHYDRO-1-(PHENYLMETHYL)-

Chemical Property of JNJ-18038683 free base

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 337.1345753
• Heavy Atom Count: 24
• Complexity: 390

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CNCCC2=C1C(=NN2CC3=CC=CC=C3)C4=CC=C(C=C4)Cl

Technology Process of JNJ-18038683 free base

There total 9 articles about JNJ-18038683 free base 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:

1-benzyl-3-(4-chlorophenyl)-1,4,6,7-tetrahydroindazol-5-one oxime (851376-93-7) → 1-benzyl-3-(4-chloro-phenyl)-1,4,5,6,7,8-hexahydro-1,2,5-triaza-azulene + 1-benzyl-3-(4-chlorophenyl)-1,4,5,6,7,8-hexahydro-1,2,6-triazaazulene (851373-91-6)

Guidance literature:

1-benzyl-3-(4-chlorophenyl)-1,4,6,7-tetrahydroindazol-5-one oxime; With diisobutylaluminium hydride; In dichloromethane; toluene; at 0 - 20 ℃; for 12h;

With sodium fluoride; In dichloromethane; water; toluene; for 1h;

Reference yield:

1-benzyl-3-(4-chloro-phenyl)-6-(4-methoxy-benzyl)-1,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene (1148136-74-6) → 1-benzyl-3-(4-chlorophenyl)-1,4,5,6,7,8-hexahydro-1,2,6-triazaazulene (851373-91-6)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; Product distribution / selectivity;

Reference yield:

3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-1H-1,2,6-triazaazulene-6-carboxylic acid tert-butyl ester (851377-09-8) → 1-benzyl-3-(4-chlorophenyl)-1,4,5,6,7,8-hexahydro-1,2,6-triazaazulene (851373-91-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

1.2: 15 h / 20 °C / Inert atmosphere

2.1: 1,1'-bis-(diphenylphosphino)ferrocene; sodium carbonate; tetrabutylammomium bromide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; water / 3 h / Reflux; Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium tert-butylate; tetrabutylammomium bromide; sodium carbonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; toluene; 2.1: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.tetlet.2021.152843

upstream raw materials:

1-benzyl-3-(4-chlorophenyl)-1,4,6,7-tetrahydroindazol-5-one oxime

1-benzyl-3-(4-chloro-phenyl)-6-(4-methoxy-benzyl)-1,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene

N-tert-butyloxycarbonylpiperidin-4-one

5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester