365998-36-3

Basic information

• Product Name: (5H-Pyrrolo[3,4-d]thiazole-5-carboxylic acid,2-[[[(1R,2S,5S)-2-[[(5-chloro-1H-indol-2-yl)carbonyl]aMino]-5-[(diMethylaMino)carbonyl]cyclohexyl]aMino]carbonyl]-4,6-dihydro-,1,1-diMethylethyl ester
• Synonyms: (5H-Pyrrolo[3,4-d]thiazole-5-carboxylic acid,2-[[[(1R,2S,5S)-2-[[(5-chloro-1H-indol-2-yl)carbonyl]aMino]-5-[(diMethylaMino)carbonyl]cyclohexyl]aMino]carbonyl]-4,6-dihydro-,1,1-diMethylethyl ester;Edoxaban INTERMEDIATES Ⅰ;Edoxaban INTERMEDIATES Ⅱ;Edoxaban INTERMEDIATES Ⅲ;EthanediaMide iMpurity A;CarbaMic acid, N-[(1R,2S,5S)-2-aMino-5-[(diMethylaMino)carbonyl]cyclohexyl]-, 1,1-diMethylethyl ester;InterMediate of Edoxaban;tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate
• CAS NO: 365998-36-3
• Molecular Formula: C₁₄H₂₇N₃O₃
• Molecular Weight: 285.38248
• EINECS: 1592732-453-0
• Mol File: 365998-36-3.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 434.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.09±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 11.90±0.60(Predicted)
• CAS DataBase Reference: (5H-Pyrrolo[3,4-d]thiazole-5-carboxylic acid,2-[[[(1R,2S,5S)-2-[[(5-chloro-1H-indol-2-yl)carbonyl]aMino]-5-[(diMethylaMino)carbonyl]cyclohexyl]aMino]carbonyl]-4,6-dihydro-,1,1-diMethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (5H-Pyrrolo[3,4-d]thiazole-5-carboxylic acid,2-[[[(1R,2S,5S)-2-[[(5-chloro-1H-indol-2-yl)carbonyl]aMino]-5-[(diMethylaMino)carbonyl]cyclohexyl]aMino]carbonyl]-4,6-dihydro-,1,1-diMethylethyl ester(365998-36-3)
• EPA Substance Registry System: (5H-Pyrrolo[3,4-d]thiazole-5-carboxylic acid,2-[[[(1R,2S,5S)-2-[[(5-chloro-1H-indol-2-yl)carbonyl]aMino]-5-[(diMethylaMino)carbonyl]cyclohexyl]aMino]carbonyl]-4,6-dihydro-,1,1-diMethylethyl ester(365998-36-3)

Safety Data

• Hazardous Substances Data: 365998-36-3(Hazardous Substances Data)

Usage

Uses

tert-Butyl [(1R,2S,5S)-2-Amino-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate is a reagent used in the synthesis of cis-1,2-diaminocyclohexane derivative, which are factor Xa (fXa) inhibitors.

Upstream product

• 480450-69-9 tert-butyl N-[(1R,2S,5S)-2-azido-5-[(dimethylamino)carbonyl]cyclohexyl]carbamate 
• 929693-35-6 (1S,3S,6R)-N,N-dimethyl-7-oxabicyclo[4.1.0]heptane-3-carboxamide 
• 929693-36-7 (1S,3R,4R)-3-amino-4-hydroxy-N,N-dimethyl cyclohexanecarboxamide 
• 929693-30-1 (1S,3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-N,N-dimethylcyclohexanecarboxamide 
• 929693-31-2 {(1R,2R,4S)-2-[(tert-butoxycarbonyl)amino]-4-[(dimethylamino)carbonyl]cyclohexyl}methanesulfonate 
• 139893-81-5 (1S,4S,5S)-4-bromo-6-oxabicyclo<3.2.1>octan-7-one 
• 67976-82-3 (1S)-3-cyclohexene-1-carboxylic acid (R)-(+)-α-methylbenzylamine salt 
• 5708-19-0 (1S)-3-cyclohexenecarboxylic acid 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 19914-91-1 (1RS,4RS,5RS)-4-bromo-6-oxabicyclo<3.2.1>octan-7-one 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 480452-40-2 tert-Butyl (1R,2S,5S)-5-[(dimethylamino)carbonyl]-2-{[2-(4-fluoroanilino)-2-oxoethanethioyl]amino}cyclohexyl-carbamate 
• 480449-95-4 (1S,2R,4S)-N₂-(tert-Butoxycarbonyl)-N₁-[(6-chloro-quinolin-2-yl)carbonyl]-4-(N,N-dimethylcarbamoyl)-1,2-cyclohexanediamine 
• 480452-36-6 carbamic acid, N-[(1R,2S,5S)-2-[[2-[(5-chloro-2-pyridinyl)amino]-2-oxoacetyl]amino]-5-[(dimethylamino)carbonyl]cyclohexyl]-1,1-dimethylethyl ester 
• 480449-70-5 edoxaban 
• 480449-71-6 [14C]-Edoxaban tosylate 
• 1353893-22-7 tert-butyl {(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl}carbamate monooxalate monohydrate 
• 1227058-05-0 tert-butyl (1R,2S,5S)-2-{[(7-chloroimidazo[1,2-a]pyridin-2-yl)carbonyl]amino}-5-[(dimethylamino)carbonyl]cyclohexylcarbamate 
• 480450-94-0 t-butyl {(1R,2S,5S)-2-{[(5-chloro-3-fluoroindol-2-yl)carbonyl]amino}-5-[(dimethylamino)carbonyl]cyclohexyl}carbamate 
• 500571-54-0 Methyl 2-[((1S,2R,4S)-4-[(dimethylamino)carbonyl]-2-{[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]amino}cyclohexyl)amino]-2-(methoxyimino)-acetate 
• 480451-79-4 tert-Butyl (1R,2S,5S)-2-{[2-(4-chloroanilino)-2-(hydroxyimino)acetyl]amino}-5-[(dimethylamino)carbonyl]-cyclohexylcarbamate 

Relevant articles and documents

Preparation method of edoxaban intermediate

The invention relates to the technical field of medicines, and particularly discloses a preparation method of an edoxaban intermediate. The preparation method comprises the following steps: carrying out diene synthesis on a thiophene derivative of a compound II and acrylic acid, and carrying out chiral resolution to obtain a compound IV; carrying out amidation reaction with dimethylamine hydrochloride to obtain a compound V; reacting with di-tert-butyl dicarbonate in a hydrogen atmosphere to obtain a compound VI and a compound VI'; and carrying out amino deprotection and chiral resolution to obtain a compound I, namely the edoxaban intermediate. The preparation method provided by the invention has the advantages of concise operation steps, high diastereomer selectivity, facilitation of improvement of the product yield and reduction of the production cost, no use of a dangerous reagent sodium azide, no involvement of a low-temperature reaction, reduction of the production risk, and guarantee of the safety and the operability of the reaction.

Preparation method and intermediate of chiral diamine compound

The present invention relates to a preparation method and an intermediate of a chiral diamine compound, wherein the chiral diamine compound is used for preparing the key intermediate of a small molecule oral anticoagulant edoxaban. According to the present invention, the steps of the preparation method of the chiral diamine compound 2 and the key intermediate 2B are defined in the specification, wherein the group R is preferably selected from methoxy, ethoxy and dimethylamino.

Imide intermediate compound as well as preparation method and application thereof

The invention discloses an imide intermediate compound adopting a structure shown as a formula (II) and a preparation method of the imide intermediate compound. The imide intermediate compound can beused as an intermediate for preparing a precursor compound of an anticoagulant edoxaban. The preparation method comprises the following steps: adding a compound adopting a structure shown as a formula(I) into a reaction solvent, introducing a compound containing a nucleophilic amino group into a compound adopting the structure shown as the formula (I) under the action of an azo reagent and ternary substituted phosphorus, converting a hydroxyl group at 1st position into an amino group, and reversing the configuration to obtain the intermediate adopting the structure shown as the formula (II);adding the imide intermediate in alkali, and removing a protecting group to obtain the precursor compound, adopting the structure shown as a formula (III), of the edoxaban. Use of explosive or highlytoxic compounds in the preparation process and a subsequent high-pressure hydrogenation reaction are avoided, not only the chiral purity of a product is greatly improved, but also the production costcan be reduced, safety hazards in the production process are solved, the production cycle is greatly shortened, and the production efficiency is significantly improved.