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Chemistry
Heterocyclic Building Blocks
Tetrahydroisoquinolines
Argatroban
Chemistry
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Heterocyclic Building Blocks
Metabolic Enzyme
Tetrahydroisoquinolines
Tetrahydroquinolines Thrombin

[ CAS No. 74863-84-6 ] {[proInfo.proName]}

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Chemical Structure| 74863-84-6
Chemical Structure| 74863-84-6
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Product Details of [ 74863-84-6 ]

CAS No. :74863-84-6 MDL No. :MFCD23102419
Formula : C23H36N6O5S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 508.63 Pubchem ID :-
Synonyms :
MCI-9038;MD-805;Argipidine

Safety of [ 74863-84-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H319-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 74863-84-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 74863-84-6 ]

[ 74863-84-6 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 367952-84-9 ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogen In ethanol; acetic acid at 20℃; for 20h;
Reference： [1]Cossy, Janine; Belotti, Damien [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 15, p. 1989 - 1992]
  • 2
  • [ 626-58-4 ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: 100 percent / Et3N / CH2Cl2 / 0 - 20 °C 2.1: s-BuLi; TMEDA / diethyl ether / -90 °C 2.2: 35 percent / diethyl ether / -90 - 20 °C 3.1: 99 percent / HCl / ethyl acetate / 0 - 20 °C 4.1: 100 percent / HCl / ethyl acetate / 20 °C 5.1: 86 percent / Et3N / CH2Cl2 / 0 °C 6.1: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
Reference： [1]Cossy, Janine; Belotti, Damien [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 15, p. 1989 - 1992]
  • 3
  • [ 123387-50-8 ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: s-BuLi; TMEDA / diethyl ether / -90 °C 1.2: 35 percent / diethyl ether / -90 - 20 °C 2.1: 99 percent / HCl / ethyl acetate / 0 - 20 °C 3.1: 100 percent / HCl / ethyl acetate / 20 °C 4.1: 86 percent / Et3N / CH2Cl2 / 0 °C 5.1: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
Reference： [1]Cossy, Janine; Belotti, Damien [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 15, p. 1989 - 1992]
  • 4
  • Nα-(tert-butoxycarbonyl)-Nω-nitro-arginine [ No CAS ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Et3N / -35 °C 2: 100 percent / HCl / ethyl acetate / 20 °C 3: 86 percent / Et3N / CH2Cl2 / 0 °C 4: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
Reference： [1]Cossy, Janine; Belotti, Damien [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 15, p. 1989 - 1992]
  • 5
  • [ 74863-82-4 ]
  • [ 74863-84-6 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1989 - 1992
  • 6
  • trans-benzyl 4-methylpipecolic acid ester [ No CAS ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 100 percent / HCl / ethyl acetate / 20 °C 2: 86 percent / Et3N / CH2Cl2 / 0 °C 3: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
Reference： [1]Cossy, Janine; Belotti, Damien [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 15, p. 1989 - 1992]
  • 7
  • benzyl trans-N-Boc-4-methylpipecolic acid ester [ No CAS ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 99 percent / HCl / ethyl acetate / 0 - 20 °C 2: 100 percent / HCl / ethyl acetate / 20 °C 3: 86 percent / Et3N / CH2Cl2 / 0 °C 4: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
Reference： [1]Cossy, Janine; Belotti, Damien [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 15, p. 1989 - 1992]
  • 8
  • C16H29N5O8 [ No CAS ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 100 percent / HCl / ethyl acetate / 20 °C 2: 86 percent / Et3N / CH2Cl2 / 0 °C 3: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
Reference： [1]Cossy, Janine; Belotti, Damien [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 15, p. 1989 - 1992]
  • 9
  • [ 367952-82-7 ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 100 percent / HCl / ethyl acetate / 20 °C 2: 86 percent / Et3N / CH2Cl2 / 0 °C 3: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
Reference： [1]Cossy, Janine; Belotti, Damien [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 15, p. 1989 - 1992]
  • 10
  • C20H30N6O5*ClH [ No CAS ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 86 percent / Et3N / CH2Cl2 / 0 °C 2: 90 percent / H2 / 10 percent Pd/C / ethanol; acetic acid / 20 h / 20 °C / 760 Torr
Reference： [1]Cossy, Janine; Belotti, Damien [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 15, p. 1989 - 1992]
YieldReaction ConditionsOperation in experiment
94% 1 (E) (2R,4R)-1-[N2 -(3methyl-1,2,3,4-tetrahydro-8-quinolinesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid (E) (2R,4R)-1-[N2 -(3methyl-1,2,3,4-tetrahydro-8-quinolinesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid To a solution of 3.00 g of 1-[NG -nitro-N2 -(3-methyl-8-quinolinesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid in 40 ml of ethanol and 10 ml of acetic acid was added 0.3 g of 5% palladium carbon and then the mixture was shaken under 50 kg/cm2 hydrogen pressure at 80° C. for 4 hrs. At the end of this period, the solution was filtered to remove the catalyst and evaporated. The residual viscous oil was shaken with a mixture of 30 ml of chloroform and 30 ml of saturated sodium bicarbonate solution. The chloroform layer was washed with 30 ml of water and evaporated. The resulting crude crystal was recrystallized from ethanol to give 2.6 g (94% yield) of (2R,4R)-1-[N2 -(3-methyl-1,2,3,4-tetrahydro-8-quinolinesulfonyl)-L-arginyl]-4methyl-2-piperidinecarboxylic acid, m.p. 188°-191° C. IR (KBr): 3,400, 1,620, 1,460, 1,380 cm-1 NMR: 100 MHz in CD3 OD δ-value; 6.5 (triplet 1H) 7.1 (doublet 1H), 7.4 (doublet 1H)
As the arginineamides used in the invention, the following compounds are exemplified. (2R,4R)-1- [N2 -(3-isopropoxybenzenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid; (2R,4R)-1- [N2 -(3,5-dimethyl-4-propoxybenzenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid; (2R,4R)-1- [N2 -(5,6,7,8-tetrahydro-2-naphthalenesulfon)-yl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid; (2R,4R)-1-[N2 -(5-dimethylamino-1-naphthalenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid; (2R,4R)-1-[N2 -(3-methyl-1,2,3,4-tetrahydro-8-quinoline-sulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid; (2R,4R)-1-[N2 -(2-dibenzothiophenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid; (2R,4R)-1-[N2 -(2,4-dimethoxy-3-butoxybenzenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid; (2R,4R)-1-[N2 -(3,5-dimethyl-4-propoxybenzenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid; (2R,4R)-1-[N2 -(3-ethyl-1,2,3,4-tetrahydro-8-quinoline-sulfonyl)-L-arginyl] 4-methyl-2-piperidinecarboxylic acid; ...
Specific examples of the compounds of the present invention are shown below. (2R,4R)-1-[N2 -(3-isopropoxybenzenesulfonyl)-L-arginyl]4-methyl-2-piperidinecarboxylic acid, (2R,4R)-1-[N2 -(3,5-dimethyl-4-propoxybenzenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid, (2R,4R)-1-[N2 -(5,6,7,8-tetrahydro-2-naphthalenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid, (2R,4R)-1-[N2 -(5-dimethylamino-1-naphthalenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid, (2R,4R)-1-[N2 -(3-methyl-1,2,3,4-tetrahydro-8-quinoline-sulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid, (2R,4R)-1-[N2 -(2-dibenzothiophenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid, (2R,4R)-1-[N2 -(2,4-dimethoxy-3-butoxybenzenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid, (2R,4R)-1-[N2 -(3,5-dimethyl-4-propoxybenzenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid, (2R,4R)-1-[N2 -(3-ethyl-1,2,3,4-tetrahydro-8-quinoline-sulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid, ...
Specific examples of the compounds of the present invention are shown below. ... (2R,4R)-1-[N2-(5,6,7,8-tetrahydro-2-naphthalenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid, (2R,4R)-1-[N2-(5-dimethylamino-1-naphthalenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid, (2R,4R)-1-[N2-(3-methyl-1,2,3,4-tetrahydro-8-quinoline-sulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid, (2R,4R)-1-[N2-(2-dibenzothiophenesulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid, ...

  • 12
  • [ 74874-10-5 ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
93% With hydrogen In methanol; acetic acid at 85℃; for 8h; 3 Example 2: treatment of the crude argatroban with NaOH and crystallization from normal propanolA one-litre glass autoclave was fed with 50 g of (2f?,4/:?)-1 -[NG-nitro-N2-(3-methyl- 8-quinolinesulphonyl)-L-arginyl]-4-methyl-2-piperidine carboxylic acid, 375 ml of methanol, 95 ml of acetic acid and 16.4 g of palladium on 5% carbon (60% wetted).The mixture thus obtained was treated, under vigorous stirring, at 85QC in a 8.5 bar hydrogen atmosphere for 8 hours. The mass was then cooled to room temperature and the catalyst removed by filtration. The obtained solution was concentrated to a residue under reduced pressure.570 ml of methylene chloride was added to the oily residue obtained and the solution divided into two parts. Half of the obtained solution was fed into a jacketed 1 -litre glass reactor and to it 120 ml of water were added. The acetic acid residue was then neutralized by addition of a 30% sodium hydroxide solution until pH=7.5 was achieved. In order to obtain a net separation between the organic phase and aqueous phase 12 ml of methanol were then added. The mixture was maintained under stirring for 1 hour, then the aqueous phase was removed and the organic phase washed twice with 120 ml of water, adding each time the necessary quantity of methanol to achieve a good separation.The solution in methylene chloride thus obtained was then percolated into a 500 ml jacketed reactor containing 140 ml of 1 -propanol. The mass was then heated to 55QC to distil off the dichloromethane present. The solution was then cooled to 0QC over a period of 2 hours and maintained at this temperature for 2 hours.The solid obtained by crystallization was filtered off and dried at 50QC under vacuum for 16 hours, giving 17.0 g of purified (2fl,4fl)-4-methyl-1 -[N2-[(1 ,2,3,4- tetrahydro-3-methyl-8- quinolylsulphonyl]-L-arginyl]pipecolic acid (IV). Yield = 73%. Example 3: treatment of crude argatroban without neutralization and with crystallization from isopropanolHalf of the compound (III) solution in dichloromethane obtained in example 2 was extracted twice with a mixture of 120 ml of water and 12 ml of methanol. The solution in methylene chloride thus obtained was then percolated into a 500 ml jacketed reactor containing 140 ml of 2-propanol, the mass obtained was concentrated by distillation.When the distillation was complete the temperature was brought to 90QC, the mass left under agitation for 1 hour, cooled to 20QC and finally to 0QC where it was maintained for 2 hours.The solid obtained by crystallization was filtered off and dried at 50QC under vacuum for 16 hours to give 21.5 g of purified (2fl,4fl)-4-methyl-1 -[N2-[(1 ,2,3,4- tetrahydro-3-methyl-8-quinolylsulphonyl]-L-arginyl]pipecolic acid (IV). Yield = 93%.
With palladium on activated charcoal; hydrogen; acetic acid In ethanol
Reference： [1]Current Patent Assignee: H. LUNDBECK A/S - WO2009/124906, 2009, A2 Location in patent: Page/Page column 20-21
[2]van der Heijden, Gydo; van Schaik, Timo B.; Mouarrawis, Valentinos; de Wit, Martin J. M.; Velde, Christophe M. L. Vande; Ruijter, Eelco; Orru, Romano V. A. [European Journal of Organic Chemistry, 2019, vol. 2019, # 31-32, p. 5313 - 5325]
  • 13
  • Nω,Nω'-bis((benzyloxy)carbonyl)-N2-((3-methylquinolin-8-yl)sulfon-yl)-L-arginine [ No CAS ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2,2,2-trifluoroethanol / 20 °C 2: sodium hydroxide / water; ethanol / 1 h / Reflux 3: hydrogen; acetic acid; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
Reference： [1]van der Heijden, Gydo; van Schaik, Timo B.; Mouarrawis, Valentinos; de Wit, Martin J. M.; Velde, Christophe M. L. Vande; Ruijter, Eelco; Orru, Romano V. A. [European Journal of Organic Chemistry, 2019, vol. 2019, # 31-32, p. 5313 - 5325]
  • 14
  • 1-(Nω,Nω'-bis(1-(benzyloxy)carbonyl)-N2-((3-methylquinolin-8-yl)sulfonyl)-L-arginyl)-N-(6-bromopyridin-2-yl)-4-methylpiperidine-2-carboxamide [ No CAS ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / water; ethanol / 1 h / Reflux 2: hydrogen; acetic acid; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
Reference： [1]van der Heijden, Gydo; van Schaik, Timo B.; Mouarrawis, Valentinos; de Wit, Martin J. M.; Velde, Christophe M. L. Vande; Ruijter, Eelco; Orru, Romano V. A. [European Journal of Organic Chemistry, 2019, vol. 2019, # 31-32, p. 5313 - 5325]
  • 15
  • [ 120267-95-0 ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trifluoroacetic acid / dichloromethane / 0 °C 2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; water / 16 h / 0 - 20 °C 3: 2,2,2-trifluoroethanol / 20 °C 4: sodium hydroxide / water; ethanol / 1 h / Reflux 5: hydrogen; acetic acid; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
Reference： [1]van der Heijden, Gydo; van Schaik, Timo B.; Mouarrawis, Valentinos; de Wit, Martin J. M.; Velde, Christophe M. L. Vande; Ruijter, Eelco; Orru, Romano V. A. [European Journal of Organic Chemistry, 2019, vol. 2019, # 31-32, p. 5313 - 5325]
  • 16
  • H-L-Arg(Cbz)<SUB>2</SUB>-OH [ No CAS ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran; water / 16 h / 0 - 20 °C 2: 2,2,2-trifluoroethanol / 20 °C 3: sodium hydroxide / water; ethanol / 1 h / Reflux 4: hydrogen; acetic acid; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr
Reference： [1]van der Heijden, Gydo; van Schaik, Timo B.; Mouarrawis, Valentinos; de Wit, Martin J. M.; Velde, Christophe M. L. Vande; Ruijter, Eelco; Orru, Romano V. A. [European Journal of Organic Chemistry, 2019, vol. 2019, # 31-32, p. 5313 - 5325]
  • 17
  • (2R,4R)-1-(Nω′-((benzyloxy)carbonyl)-N2-((3-methylquinolin-8-yl)sulfonyl)-L-arginyl)-4-methylpiperidine-2-carboxylic acid [ No CAS ]
  • [ 74863-84-6 ]
YieldReaction ConditionsOperation in experiment
88% With palladium 10% on activated carbon; hydrogen; acetic acid In ethanol at 20℃; for 16h;
Reference： [1]van der Heijden, Gydo; van Schaik, Timo B.; Mouarrawis, Valentinos; de Wit, Martin J. M.; Velde, Christophe M. L. Vande; Ruijter, Eelco; Orru, Romano V. A. [European Journal of Organic Chemistry, 2019, vol. 2019, # 31-32, p. 5313 - 5325]

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