851784-82-2

Basic information

• Product Name: 2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid
• Synonyms: 2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid;5,7-Dichloro-3,4-dihydro-2,6(1H)-isoquinolinedicarboxylic acid 2-(1,1-dimethylethyl) ester;Lifitegrast intermediate;N-Boc- 5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid;2,6(1H)-Isoquinolinedicarboxylic acid, 5,7-dichloro-3,4-dihydro-, 2-(1,1-dimethylethyl) ester;-(Tert-Butoxycarbonyl-5,7-Dichloro-1,2,3,4-T..
• CAS NO: 851784-82-2
• Molecular Formula: C₁₅H₁₇Cl₂NO₄
• Molecular Weight: 346.20578
• EINECS: -0
• Mol File: 851784-82-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 468.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.379±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.87±0.20(Predicted)
• CAS DataBase Reference: 2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid(851784-82-2)
• EPA Substance Registry System: 2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid(851784-82-2)

Safety Data

• Hazardous Substances Data: 851784-82-2(Hazardous Substances Data)

Usage

Uses

2-(tert-Butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic Acid is a reagent in the preparation of N-benzofuranylcarbonyl dichlorotetrahydroisoquinolinylcarbonylmethylsulfonyl L-phenylalanine as LFA-1 inhibitor and polymorph thereof for the treatment of LFA -1 mediated diseases.

Synthesis

Boc-protection was used for the ring nitrogen in the intermediates 21 and 22.Compound 5 was deprotected with HC1 in dioxane to produce compound 23 in better than 97%yield. Boc-protection was introduced, using di-tert-butyl dicarbonate (1 .1 equivalent), and compound 21 was obtained in better than 95% yield. Compound 10 was coupled with compound 21 to obtain compound 22, using HATU and triethylamine in DMF. The product, compound 22, was obtained in quantitative yield, and greater than 90% purity. Deprotection with HC1 yielded the compound of Formula 12 in 97.4% yield.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 1194550-56-5 5,7-dichloro-2-trityl-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid 
• 1289646-72-5 C₂₈H₂₃Cl₂N 
• 73075-47-5 5,7-dichloro-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 14046-52-7 N-(2-chloroethyl)-3,5-dichlorobenzylamine hydrochloride 
• 10203-08-4 3,5-dichlorobenzaldehyde 
• 851784-76-4 tert-butyl 5,7-dichloro-6-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1609545-55-2 C₉H₉Cl₂NO*C₇H₈O₃S 
• 1289646-93-0 5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid hydrochloride 
• 89315-56-0 5,7-dichloro-1,2,3,4-tetrahydroisoquinoline 
• 851784-78-6 C₁₅H₁₆Cl₂F₃NO₅S 
• 14446-24-3 6-hydroxy-1,2,3,4-tetrahydroisoquinoline 
• 73075-58-8 5,7-dichloro isoquinoline 

Downstream Products

• 851784-84-4 C₂₄H₂₇Cl₂N₃O₆S 
• 1194550-65-6 benzyl (S)-2-(5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-[3-(methylsulfonyl)phenyl]propanoate hydrochloride 
• 1194550-67-8 ((S)-benzyl 2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-methylsulfonyl)phenyl)propanoate 
• 1025967-78-5 (S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid 
• 1194550-61-2 benzyl (S)-2-[2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido]-3-[3-(methylsulfonyl)phenyl]propanoate 
• 851785-70-1 (S)-2-(5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid 

Relevant articles and documents

INHIBITORS OF ALPHA 2 BETA 1 INTEGRIN AND METHODS OF USE THEREOF

Disclosed herein, inter alia, are inhibitors of alpha 2 beta 1 integrin and methods of using the same.

A method for synthesizing intermediate advantage non-si te (by machine translation)

The invention discloses a method of preparing intermediates of advantage non-si te, comprises the following steps: (1) heating compound 1, tetramethyl diethylamine and butyl lithium treatment, adding chloromethane acid benzyl ester, in - 70 °C following temperature reaction, to obtain compound 2; (2) taking compound 2 with the strong alkali solution reaction, after the reaction adjusting PH to 3 - 4, extraction, to obtain compound 3. The advantage non-si te intermediates prepared by the process of a high degree of selectivity, the controllability is strong, good stability, the total yield is high, suitable for commercial scale production. (by machine translation)

Discovery of tetrahydroisoquinoline (THIQ) derivatives as potent and orally bioavailable LFA-1/ICAM-1 antagonists

This letter describes the discovery of a novel series of tetrahydroisoquinoline (THIQ)-derived small molecules that potently inhibit both human T-cell migration and super-antigen induced T-cell activation through disruption of the binding of integrin LFA-1 to its receptor, ICAM-1. In addition to excellent in vitro potency, 6q shows good pharmacokinetic properties and its ethyl ester (6t) demonstrates good oral bioavailability in both mouse and rat. Either intravenous administration of 6q or oral administration of its ethyl ester (6t) produced a significant reduction of neutrophil migration in a thioglycollate-induced murine peritonitis model.