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74863-84-6

Basic Information
CAS No.: 74863-84-6
Name: Argatroban
Article Data: 7
Molecular Structure:
Molecular Structure of 74863-84-6 (Argatroban)
Formula: C23H36N6O5S
Molecular Weight: 508.642
Synonyms: 2-Piperidinecarboxylicacid,1-[5-[(aminoiminomethyl)amino]-1-oxo-2-[[(1,2,3,4-tetrahydro-3-methyl-8-quinolinyl)sulfonyl]amino]pentyl]-4-methyl-,[2R-[1(2S*),2a,4b]]-[partial]-;Acova;Argatra;Argipidin;Argipidine;DK 7419;GN 1600;MCI 9038;MD 805;MQPA;Novastan;OM 805;Slonnon;
EINECS: 638-764-8
Density: 1.47 g/cm3
Melting Point: 188-189 °C
Boiling Point: 801.3 °C at 760 mmHg
Flash Point: 438.4 °C
Appearance: white to off-white crystalline solid
Hazard Symbols: Xn,N
Risk Codes: R20/21/22; R51/53
PSA: 186.09000
LogP: 3.65110
Synthetic route
74874-10-5

(2R,4R)-1-[NG-nitro-N2-(3-methyl-8-quinolinesulphonyl)-L-arginyl]-4-methyl-2-piperidine carboxylic acid

74863-84-6

argatroban

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In methanol; acetic acid at 85℃; under 6375.64 Torr; for 8h; Product distribution / selectivity;93%
With palladium on activated charcoal; hydrogen; acetic acid In ethanol under 760.051 Torr;
367952-84-9

C30H37N7O7S

74863-84-6

argatroban

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol; acetic acid at 20℃; under 760 Torr; for 20h;90%

(2R,4R)-1-(Nω′-((benzyloxy)carbonyl)-N2-((3-methylquinolin-8-yl)sulfonyl)-L-arginyl)-4-methylpiperidine-2-carboxylic acid

74863-84-6

argatroban

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; acetic acid In ethanol at 20℃; under 760.051 Torr; for 16h;88%
626-58-4

4-methylpiperidin

74863-84-6

argatroban

Conditions
ConditionsYield
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
View Scheme
123387-50-8

4-methylpiperidine-1-carboxylic acid tert-butyl ester

74863-84-6

argatroban

Conditions
ConditionsYield
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
View Scheme

Nα-(tert-butoxycarbonyl)-Nω-nitro-arginine

74863-84-6

argatroban

Conditions
ConditionsYield
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
View Scheme
74863-82-4

8-(chlorosulphonyl)-3-methylquinoline

74863-84-6

argatroban

Conditions
ConditionsYield
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
View Scheme

trans-benzyl 4-methylpipecolic acid ester

74863-84-6

argatroban

Conditions
ConditionsYield
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
View Scheme

benzyl trans-N-Boc-4-methylpipecolic acid ester

74863-84-6

argatroban

Conditions
ConditionsYield
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
View Scheme

C16H29N5O8

74863-84-6

argatroban

Conditions
ConditionsYield
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
View Scheme
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History

In 2000, argatroban(74863-84-6) was licensed by the Food and Drug Administration (FDA) for prophylaxis or treatment of thrombosis in patients with heparin-induced thrombocytopenia (HIT). In 2002, it was approved for use during percutaneous coronary interventions in patients who have HIT or are at risk for developing it.

Specification

The IUPAC name of Argatroban is (2R,4R)-1-[5-(diaminomethylideneamino)-2-[(3-methyl-1,2,3,4-tetrahydroquinolin-8-yl)sulfonylamino]pentanoyl]-4-methylpiperidine-2-carboxylic acid. With the CAS registry number 74863-84-6, it is also named as 2-Piperidinecarboxylic acid, 1-(5-((aminoiminomethyl)amino)-1-oxo-2-(((1,2,3,4-tetrahydro-3-methyl-8-quinolinyl)sulfonyl)amino)pentyl)-4-methyl-. The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals. It is white to off-white crystalline solid.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.56; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -0.43; (4)ACD/LogD (pH 7.4): -0.45; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.02; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 11; (10)#H bond donors: 7; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.674; (13)Molar Refractivity: 129.78 cm3; (14)Molar Volume: 345.7 cm3; (15)Polarizability: 51.45×10-24 cm3; (16)Surface Tension: 61.6 dyne/cm; (17)Enthalpy of Vaporization: 122.18 kJ/mol; (18)Vapour Pressure: 4.23E-27 mmHg at 25°C; (19)Rotatable Bond Count: 9; (20)Tautomer Count: 2; (21)Exact Mass: 508.246789; (22)MonoIsotopic Mass: 508.246789; (23)Topological Polar Surface Area: 189; (24)Heavy Atom Count: 35; (25)Complexity: 887.

Preparation of Argatroban: It can be obtained by the following reaction.


this product

Uses of Argatroban: It is used as an anticoagulant in individuals with thrombosis and heparin induced thrombocytopenia. The combination of argatroban and warfarin may raise the INR to greater than 5.0 without a significant increased risk of bleeding complications.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)[C@@H]3N(C(=O)C(NS(=O)(=O)c1cccc2c1NCC(C2)C)CCC/N=C(\N)N)CC[C@@H](C)C3
2. InChI:InChI=1/C23H36N6O5S/c1-14-8-10-29(18(12-14)22(31)32)21(30)17(6-4-9-26-23(24)25)28-35(33,34)19-7-3-5-16-11-15(2)13-27-20(16)19/h3,5,7,14-15,17-18,27-28H,4,6,8-13H2,1-2H3,(H,31,32)(H4,24,25,26)/t14-,15,17,18-/m1/s1