lumateperone (Tosylate)

Base Information

• Chemical Name: lumateperone (Tosylate)
• CAS No.: 1187020-80-9
• Molecular Formula: C24H28FN3O.C7H8O3S
• Molecular Weight: 565.709
• Mol file: 1187020-80-9.mol

Synonyms:lumateperone (Tosylate);ITI 007;1-(4-Fluorophenyl)-4-[(6bR,10aS)-2,3,6b,9,10,10a-hexahydro-3-methyl-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl]-1-butanone 4-methylbenzenesulfonate (1:1)

Chemical Property of lumateperone (Tosylate)

Chemical Property:

• PSA: 89.54000
• LogP: 6.30690

Purity/Quality:

99% ^*data from raw suppliers

Lumateperone tosylate ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of lumateperone (Tosylate)

There total 28 articles about lumateperone (Tosylate) 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: 78.0%

4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido-[3’,4’:4,5]-pyrrolo[1,2,3-de]quinoxalin-8-(7H)-yl)-1-(4-fluorophenyl)-1-butanone (313368-91-1) + toluene-4-sulfonic acid (104-15-4) → 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid salt (1187020-80-9)

Guidance literature:

In isopropyl alcohol; Inert atmosphere;

Reference yield:

(6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3‘,4’:4,5]pyrrolo[1,2,3-de]quinoxaline hydrochloride + toluene-4-sulfonic acid (104-15-4) + 4-(4-fluorophenyl)-4-oxo-n-butyl chloride (3874-54-2,41167-07-1) → 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid salt (1187020-80-9)

Guidance literature:

(6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3‘,4’:4,5]pyrrolo[1,2,3-de]quinoxaline hydrochloride; With sodium hydroxide; In Isopropyl acetate; water; at 0 - 30 ℃; for 0.5h; pH=12;

4-(4-fluorophenyl)-4-oxo-n-butyl chloride; With sodium carbonate; pentan-3-one; potassium iodide; In Isopropyl acetate; water; at 10 - 73 ℃; for 16h; Inert atmosphere;

toluene-4-sulfonic acid; In isopropyl alcohol; at 33 ℃;

Reference yield:

racemic cis 6-bromo-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole → 4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone toluenesulfonic acid salt (1187020-80-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: triethylamine / tetrahydrofuran / 1.5 h / 20 °C / Cooling with ice

2.1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex / toluene / 20 - 105 °C / Inert atmosphere

3.1: sodium carbonate; potassium iodide / acetone / 16 h / Reflux

4.1: hydrogenchloride / water; tetrahydrofuran / 1.5 h / 20 °C

5.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / Inert atmosphere

5.2: 1 h / 20 °C / Inert atmosphere; Cooling with ice

6.1: borane-THF / tetrahydrofuran / 1 h / Inert atmosphere; Reflux

6.2: 0.5 h / Reflux; Inert atmosphere

7.1: potassium hydroxide / butan-1-ol / 5 h / Reflux

8.1: triethylamine; potassium iodide / 1,4-dioxane; toluene / 7 h / Reflux

9.1: Chiral AD-H / ethanol / Resolution of racemate

10.1: isopropyl alcohol / 0 - 20 °C

With hydrogenchloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; borane-THF; sodium hydride; sodium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; potassium iodide; potassium hydroxide; sodium t-butanolate; In tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; mineral oil; butan-1-ol;

DOI:10.1021/jm401958n

upstream raw materials:

4-((6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido-[3’,4’:4,5]-pyrrolo[1,2,3-de]quinoxalin-8-(7H)-yl)-1-(4-fluorophenyl)-1-butanone

toluene-4-sulfonic acid

1,2,3,4-tetrahydroquinoxalin-2-one

1-nitroso-3-keto-1,2,3,4-tetrahydroquinoxaline