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120202-66-6

Basic Information
CAS No.: 120202-66-6
Name: Clopidogrel bisulfate
Molecular Structure:
Molecular Structure of 120202-66-6 (Clopidogrel bisulfate)
Formula: C16H18ClNO6S2
Molecular Weight: 419.90
Synonyms: Thieno(3,2-c)pyridine-5(4H)-acetic acid, alpha-(2-chlorophenyl)-6,7-dihydro-, methyl ester, (S)-, sulfate (1:1);Plavix;Methyl (+)-(S)-alpha-(o-chlorophenyl)-6,7-dihydrothieno(3,2-c)pyridine-5(4H)-acetate, sulfate (1:1) ; Methyl alphaS-(2-chlorophenyl)-6,7-dihydrothieno(3,2-c)pyridine-5(4H)-acetate sulfate (1:1);Iscover;(S)-( )-Methyl (2-chlorophenyl)(6,7-dihydro-4H-thieno(3,2-c)pyrid-5-yl)acetate bisulfate;Clopidogrel hemisulfate;
EINECS: 1806241-263-5
Density:
Melting Point: 184oC
Boiling Point: 423.7 °C at 760 mmHg
Flash Point: 210 °C
Solubility:
Appearance: powder
Hazard Symbols:
Risk Codes:
Safety: 22-24/25
Transport Information:
PSA: 140.76000
LogP: 3.96550
Synthetic route

(S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride

50-00-0

formaldehyd

120202-66-6

(S)-(+)-clopidogrel bisulfate

Conditions
ConditionsYield
Stage #1: (S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride; formaldehyd In methanol at 43℃; for 5h;
Stage #2: With sulfuric acid at 38℃; for 4h; Temperature;
100%
Stage #1: (S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride; formaldehyd; hydrogenchloride In water at 80 - 85℃; for 1h;
Stage #2: With sulfuric acid In methanol; acetone at 0 - 30℃; for 15h;
n/a
Stage #1: (S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride; formaldehyd at 25 - 55℃;
Stage #2: With sulfuric acid In acetic acid butyl ester at -10 - 0℃;
Stage #1: (S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride; formaldehyd In cyclohexane; water at 40℃; for 6h; Large scale;
Stage #2: With sulfuric acid In methanol; acetone at -5℃; for 8h; Solvent; Temperature; Concentration; Large scale;
72 kg
In water at 36 - 44℃;
113665-84-2

(S)-(+)-clopidogrel

120202-66-6

(S)-(+)-clopidogrel bisulfate

Conditions
ConditionsYield
With sulfuric acid In ethyl acetate at -5 - 30℃; for 3h; Temperature; Solvent;99%
With sulfuric acid In ethyl acetate at -5 - 30℃; for 3h; Temperature; Solvent; Concentration; Inert atmosphere;99%
With polyethylene glycol-200; sulfuric acid; sodium hydrogencarbonate In acetone at -5 - 20℃; for 0.0833333 - 0.116667h; pH=8; Conversion of starting material;96%
141109-20-8

methyl (S)-2-(2-chlorophenyl)-2-[2-(thien-2-yl)ethylamino]acetate

50-00-0

formaldehyd

120202-66-6

(S)-(+)-clopidogrel bisulfate

Conditions
ConditionsYield
Stage #1: methyl (S)-2-(2-chlorophenyl)-2-[2-(thien-2-yl)ethylamino]acetate; formaldehyd With sulfuric acid In chloroform at 20℃;
Stage #2: With sulfuric acid In acetone at 10℃; for 2h; Solvent; Temperature;
96.2%
223123-46-4

methyl (R)-2-(2-chlorophenyl)-2-benzenesulfonyloxyacetate

28783-41-7

6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride

120202-66-6

(S)-(+)-clopidogrel bisulfate

Conditions
ConditionsYield
Stage #1: methyl (R)-2-(2-chlorophenyl)-2-benzenesulfonyloxyacetate; 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride With sodium hydrogencarbonate In acetone for 6h; Reflux;
Stage #2: With sulfuric acid In acetone
95.2%

methyl (R)-2-(2-chlorophenyl)-2-(4-methoxybenzenesulfonyloxy)acetate

4,5,6,7-tetrahydrothieno[3,2-c]pyridine dihydrogen phosphate

120202-66-6

(S)-(+)-clopidogrel bisulfate

Conditions
ConditionsYield
Stage #1: methyl (R)-2-(2-chlorophenyl)-2-(4-methoxybenzenesulfonyloxy)acetate; 4,5,6,7-tetrahydrothieno[3,2-c]pyridine dihydrogen phosphate With N-ethyl-N,N-diisopropylamine In acetone for 6h; Reflux;
Stage #2: With sulfuric acid In acetone
94.9%

methyl (R)-2-(2-chlorophenyl)-2-(4-methylbenzenesulfonyloxy)acetate

4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide

120202-66-6

(S)-(+)-clopidogrel bisulfate

Conditions
ConditionsYield
Stage #1: methyl (R)-2-(2-chlorophenyl)-2-(4-methylbenzenesulfonyloxy)acetate; 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrobromide With triethylamine In acetone for 5h; Reflux;
Stage #2: With sulfuric acid In acetone
94.4%

clopidogrel hydrogen sulfate

120202-66-6

(S)-(+)-clopidogrel bisulfate

Conditions
ConditionsYield
In dichloromethane; water at 25 - 30℃; Conversion of starting material;
under 2 - 5 Torr; Conversion of starting material; Melting;
113665-84-2

(S)-(+)-clopidogrel

120202-69-9

methyl (R)-2-(2-chlorophenyl)-2-(4,5,6,7-tetrahydrothieno[3,2-c]pyridin-5-yl)acetate

120202-66-6

(S)-(+)-clopidogrel bisulfate

Conditions
ConditionsYield
With sulfuric acid In acetone at 15℃; for 2.5h;
Downstream Products
113665-84-2
144457-28-3
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Analytical Methods

Using Hypersil C18 (300 mm × 4.6mm, 5 μm) column, acetonitrile -0.01 mol L-1, sodium dihydrogen phosphate (65:35, phosphoric acid pH is adjusted to 3) as the mobile phase, the detection wavelength is 235 nm,the flow rate is 1.0 ml min-1 and the injection volume is 20μl. At the range of 15 ~ 150μg ml-1 ,the results showed a good linear relationship (r = 0.999 6), the average recovery was 100.5%, RSD was 1.0% (n = 4).This method is simple, sensitive and high accurate,and can be used as a method of control CLOPIDOGREL sulfate.

Specification

1.Introduction of Clopidogrel Bisulfate

The Clopidogrel Bisulfate, with its cas register number 120202-66-6, is a kind of white crystalline powder. It also can be called  Clopidogrel Bisulfate [USAN] ; (S)-( )-Methyl (2-chlorophenyl)(6,7-dihydro-4H-thieno(3,2-c)pyrid-5-yl)acetate bisulfate ; Clopidogrel hemisulfate ; Clopidogrel hydrogen sulfate ; Iscover ; Methyl (+)-(S)-alpha-(o-chlorophenyl)-6,7-dihydrothieno(3,2-c)pyridine-5(4H)-acetate, sulfate (1:1) and Methyl alphaS-(2-chlorophenyl)-6,7-dihydrothieno(3,2-c)pyridine-5(4H)-acetate sulfate (1:1). Clopidogrel Bisulfate should be stored in shady and cool warehouse and mainly used as pharmaceutical Intermediates.

2.Properties of Clopidogrel Bisulfate

(1) H-Bond Donor: 2  (2) H-Bond Acceptor: 7  (3) Storage temp.: 2-8°C
(4) Solubility DMSO: ~26 mg/mL (5) Flash Point: 210 °C (6) Enthalpy of Vaporization: 67.81 kJ/mol
(7) Boiling Point: 423.7 °C at 760 mmHg (8) Vapour Pressure: 2.19E-07 mmHg at 25°C
 

3.Structure descriptors of Clopidogrel Bisulfate

IUPAC Name: methyl
(2S)-2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,
2-c]pyridin-5-yl)acetate; sulfuric acid

InChI: InChI=1S/C16H16ClNO2S.H2O4S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-
14-11(10-18)7-9-21-14;1-5(2,3)4/h2-5,7,9,15H,6,8,10H2,1H3;(H2,1,2,3,
4)/t15-;/m0./s1

InChIKey: FDEODCTUSIWGLK-RSAXXLAASA-N

Canonical SMILES : COC(=O)C(C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)OIsomeric SMILES: COC(=O)[C@H](C1=CC=CC=C1Cl)N2CCC3=C(C2)C=CS3.OS(=O)(=O)O
 

4. Uses of Clopidogrel Bisulfate

The Clopidogrel Bisulfate  is an inhibitor of ADP-induced platelet aggregation acting by direct inhibition of adenosine diphosphate (ADP) binding to its receptor and of the subsequent ADP-mediated activation of the glycoprotein GPIIb/IIIa complex.
 

5.Safety information of Clopidogrel Bisulfate

Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
RIDADR: 1759
WGK Germany: 3
HazardClass: 8
PackingGroup: II