LCL-161

Base Information

• Chemical Name: LCL-161
• CAS No.: 1005342-46-0
• Molecular Formula: C26H33FN4O3S
• Molecular Weight: 500.637
• Hs Code.: 29341000
• Mol file: 1005342-46-0.mol

Synonyms:CS-987;LCL-161;LCL-161; LCL161;LCL-161 USP/EP/BP;LCL161, inhibitor of Apoptosis Protein (IAP) family of proteins;LCL161, 98%, inhibitor of Apoptosis Protein (IAP) family of proteins;(S)-N-((S)-1-Cyclohexyl-2-((S)-2-(4-(4-fluorobenzoyl)thiazol-2-yl)pyrrolidin-1-yl)-2-oxoethyl);N-[(1S)-1-Cyclohexyl-2-{(2S)-2-[4-(4-fluorobenzoyl)-1,3-thiazol-2-yl]-1-pyrrolidinyl}-2-oxoethyl]-N2-MethylalaninaMide;(2S)-N-[(1S)-1-Cyclohexyl-2-[(2S)-2-[4-(4-fluorobenzoyl)-2-thiazolyl]-1-pyrrolidinyl]-2-oxoethyl]-2-(methylamino)-propanamide;N-[(1S)-1-cyclohexyl-2-[(2S)-2-[4-(4-fluorobenzoyl)-2-thiazolyl]-1-pyrrolidinyl]-2-oxoethyl]-2-(methylamino)-(2S)-propanamide

Chemical Property of LCL-161

Chemical Property:

• Appearance/Colour: Off-white to yellow solid
• Boiling Point: 713.7±60.0 °C(Predicted)
• PKA: 14.25±0.46(Predicted)
• PSA: 123.13000
• Density: 1.245±0.06 g/cm3(Predicted)
• LogP: 5.01880
• Solubility.: ≥25.05 mg/mL in DMSO; insoluble in H2O; insoluble in EtOH

Purity/Quality:

98%min ^*data from raw suppliers

LCL161 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: LCL-161 is a small molecule Smac mimetic that inhibits multiple inhibitor of apoptosis (IAP) family proteins.
• Uses: LCL 161 is a second mitochondria-derived activator of caspases (SMAC) inhibitor used to prolong patient survival by increasing apoptosis of anti-tumor drugs.

Technology Process of LCL-161

There total 5 articles about LCL-161 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: 80.0%

C31H41FN4O5S (1005342-82-4) → (2S)-N-[(1S)-1-cyclohexyl-2-[(2S)-2-[4-(4-fluorobenzoyl)-1,3-thiazol-2-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide (1005342-46-0)

Guidance literature:

C₃₁H₄₁FN₄O₅S; With hydrogenchloride; In ethyl acetate; isopropyl alcohol; at 42 - 48 ℃; for 2.5h;

With potassium carbonate; In water; ethyl acetate; isopropyl alcohol; at 2 - 21 ℃; for 0.5h;

Reference yield:

tert-butyl (2S)-2-(4-(methoxy(methyl)carbamoyl)-1,3-thiazol-2-yl)pyrrolidine-1-carboxylate (1005342-77-7) → (2S)-N-[(1S)-1-cyclohexyl-2-[(2S)-2-[4-(4-fluorobenzoyl)-1,3-thiazol-2-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide (1005342-46-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene; tetrahydrofuran / 3 h / -15 - -5 °C / Inert atmosphere

1.2: 4 h / -15 - 28 °C / Inert atmosphere

2.1: hydrogenchloride / isopropyl alcohol; toluene; Isopropyl acetate / 7 - 30 °C / Inert atmosphere; Cooling with ice bath

3.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / ethyl acetate; isopropyl alcohol; toluene; water / 4.67 h / -4 - 22 °C

4.1: hydrogenchloride / ethyl acetate; isopropyl alcohol / 2.5 h / 42 - 48 °C

4.2: 0.5 h / 2 - 21 °C

With 4-methyl-morpholine; hydrogenchloride; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; Isopropyl acetate; water; ethyl acetate; isopropyl alcohol; toluene;

Reference yield:

C19H21FN2O3S (1005342-78-8) → (2S)-N-[(1S)-1-cyclohexyl-2-[(2S)-2-[4-(4-fluorobenzoyl)-1,3-thiazol-2-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide (1005342-46-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / isopropyl alcohol; toluene; Isopropyl acetate / 7 - 30 °C / Inert atmosphere; Cooling with ice bath

2.1: 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / ethyl acetate; isopropyl alcohol; toluene; water / 4.67 h / -4 - 22 °C

3.1: hydrogenchloride / ethyl acetate; isopropyl alcohol / 2.5 h / 42 - 48 °C

3.2: 0.5 h / 2 - 21 °C

With 4-methyl-morpholine; hydrogenchloride; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In Isopropyl acetate; water; ethyl acetate; isopropyl alcohol; toluene;

upstream raw materials:

C₃₁H₄₁FN₄O₅S

(S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)thiazole-4-carboxylic acid

tert-butyl (2S)-2-(4-(methoxy(methyl)carbamoyl)-1,3-thiazol-2-yl)pyrrolidine-1-carboxylate

C₁₉H₂₁FN₂O₃S

Refernces

• 1、 -. "COMBINATION OF IAP INHIBITORS AND FLT3 INHIBITORS". . . Retrieved 2010/04/23.