ChemicalBook > Product Catalog >Pharmaceutical intermediates >Heterocyclic compound >Quinoline compounds >2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid Structure
CAS No.
851784-82-2
Chemical Name:
2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid
Synonyms
5,7-Dichloro-3,4-dihydro-2,6(1H)-isoquinolinedicarboxylic acid 2-(1,1-dimethylethyl) ester;LifitegrastImpurity40;Lifitegrast intermediate;-(Tert-Butoxycarbonyl-5,7-Dichloro-1,2,3,4-T..;2-(Tert-Butoxycarbonyl)-5,7-Dichloro-1,2,3,4-Tetrahydroisoqu...;2-Boc-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic Acid;N-Boc- 5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid;2-(tert-butoxycarbonyl)-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;5,7-dichloro-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1H-isoquinoline-6-carboxylic acid
CBNumber:
CB42995940
Molecular Formula:
C15H17Cl2NO4
Molecular Weight:
346.21
MOL File:
851784-82-2.mol
Modify Date:
2023/11/3 14:46:35

2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid Properties

Boiling point 468.5±45.0 °C(Predicted)
Density 1.379±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Sparingly, Sonicated), Methanol (Slightly)
pka 1.87±0.20(Predicted)
form Solid
color White to Off-White
InChI InChI=1S/C15H17Cl2NO4/c1-15(2,3)22-14(21)18-5-4-9-8(7-18)6-10(16)11(12(9)17)13(19)20/h6H,4-5,7H2,1-3H3,(H,19,20)
InChIKey JXBQRXIJBFUZMR-UHFFFAOYSA-N
SMILES C1C2=C(C(Cl)=C(C(O)=O)C(Cl)=C2)CCN1C(OC(C)(C)C)=O

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
HS Code  2933499090

2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid Chemical Properties,Uses,Production

Description

2-(tert-Butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic Acid is a carboxylic acid derivative of tetrahydroisoquinoline with a Boc group and two chlorine atoms attached to the tetrahydroisoquinoline ring. It may exhibit various biological activities, such as anticancer, anti-inflammatory, and anticonvulsant properties, depending on the nature and position of the substituents.

Synthesis

Synthesis_851784-82-2
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.

2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid Preparation Products And Raw materials

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2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid Spectrum

2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid Lifitegrast intermediate N-Boc- 5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid 2-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.. 5,7-dichloro-2-[(2-methylpropan-2-yl)oxycarbonyl]-3,4-dihydro-1H-isoquinoline-6-carboxylic acid 2-(Tert-Butoxycarbonyl)-5,7-Dichloro-1,2,3,4-Tetrahydroisoqu... 5,7-Dichloro-2-{[(2-methyl-2-propanyl)oxy]carbonyl}-1,2,3,4-tetrahydro-6-isoquinolinecarboxylic acid 5,7-Dichloro-3,4-dihydro-2,6(1H)-isoquinolinedicarboxylic acid 2-(1,1-dimethylethyl) ester LifitegrastImpurity40 851784-82-2 1194550-65-5 C15H17Cl2NO4 851784-82-2