(6S)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxamide

Base Information

• Chemical Name: (6S)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxamide
• CAS No.: 848193-72-6
• Molecular Formula: C₁₄H₁₅ClN₂O
• Molecular Weight: 262.739
• European Community (EC) Number: 635-897-3
• DSSTox Substance ID: DTXSID40358759
• Nikkaji Number: J3.224.562E
• Wikidata: Q27454741
• Pharos Ligand ID: 63JBXFDQGAKR
• ChEMBL ID: CHEMBL198609
• Mol file: 848193-72-6.mol

Synonyms:CHIC-35;848193-72-6;SIRT1 Inhibitor IV, (S)-35;CHIC35;(6S)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxamide;CHEMBL198609;Compound (S)-35;(S)-2-Chloro-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole-6-carboxamide;SCHEMBL8257650;DTXSID40358759;CHEBI:142489;BDBM50178775;AKOS040748127;NCGC00485645-01;CHIC-35, >=97% (chiral, HPLC);HY-111303;CS-0034887;Q27454741;SIRT1 Inhibitor IV, (S)-35 - CAS 848193-72-6;(6S)-2-Chloro-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole-6-carboxamide;(S)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxamide;(6S)-2-Chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6beta-carboxamide;(S)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxylic acid amide

Chemical Property of (6S)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxamide

Chemical Property:

• PSA: 59.87000
• LogP: 4.26630
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10mg/mL
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 262.0872908
• Heavy Atom Count: 18
• Complexity: 336

Purity/Quality:

97% ^*data from raw suppliers

SIRT1 Inhibitor IV, (S)-35 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2=C(C(C1)C(=O)N)NC3=C2C=C(C=C3)Cl
• Isomeric SMILES: C1CCC2=C([C@H](C1)C(=O)N)NC3=C2C=C(C=C3)Cl

Technology Process of (6S)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxamide

There total 20 articles about (6S)-2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxamide 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: 21.0%

methyl 2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxylate (871586-90-2) → 2-chloro-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole-6-carboxylic acid amide (371219-74-8,848193-72-6)

Guidance literature:

With ammonia; In methanol; at 90 ℃; for 48h; Inert atmosphere;

Reference yield:

methyl 3-bromo-2-oxo-1-cycloheptanecarboxylate (871586-89-9) → 2-chloro-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole-6-carboxylic acid amide (371219-74-8,848193-72-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 140 °C

2: 2 g / NH₃ / methanol / 48 h / 90 °C

With ammonia; In methanol;

DOI:10.1021/jm050522v

Reference yield:

2-(methoxycarbonyl)cycloheptanone (52784-32-4) → 2-chloro-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole-6-carboxylic acid amide (371219-74-8,848193-72-6)

Guidance literature:

Multi-step reaction with 3 steps

1: Br₂ / CCl₄ / 96 h / 20 °C

2: 140 °C

3: 2 g / NH₃ / methanol / 48 h / 90 °C

With ammonia; bromine; In methanol; tetrachloromethane;

DOI:10.1021/jm050522v

upstream raw materials:

methyl 2-chloro-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-6-carboxylate

methyl 3-bromo-2-oxo-1-cycloheptanecarboxylate

2-(methoxycarbonyl)cycloheptanone

2-chloro-5,6,7,8,9,10-hexahydro-cyclohepta[b]indole-6-carboxylic acid amide

Refernces

• 1、 Fyfe, James W. B.,Hutchings-Goetz, Luke S.,Snaddon, Thomas N.,Yang, Chao. "Enantioselective Syntheses of Strychnos and Chelidonium Alkaloids through Regio- and Stereocontrolled Cooperative Catalysis". supporting information. p. 17556 - 17564. Retrieved 2020/08/14.
• 2、 Napper, Andrew D.,Hixon, Jeffrey,McDonagh, Thomas,Keavey, Kenneth,Pons, Jean-Francois,Barker, Jonathan,Yau, Wei Tsung,Amouzegh, Patricia,Flegg, Adam,Hamelin, Estelle,Thomas, Russell J.,Kates, Michael,Jones, Stephen,Navia, Manuel A.,Saunders, Jeffrey O.,DiStefano, Peter S.,Curtis, Rory. "Discovery of indoles as potent and selective inhibitors of the deacetylase SIRT1". . p. 8045 - 8054. Retrieved 2007/10/03.