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| CAS No.: | 113665-84-2 |
|---|---|
| Name: | Clopidogrel |
| Molecular Structure: | |
|
|
|
| Formula: | C16H16ClNO2S |
| Molecular Weight: | 321.828 |
| Synonyms: | Clopidogre;Thieno(3,2-c)pyridine-5(4H)-acetic acid, alpha-(2-chlorophenyl)-6,7-dihydro-, methyl ester, (S)-;methyl (2S)-2-(2-chlorophenyl)-2-(9-thia-4-azabicyclo[4.3.0]nona-7,10-dien-4-yl)acetate;Thieno[3,2-c]pyridine-5(4H)-acetic acid,R-(2-chlorophenyl)-6,7-dihydro-,methyl ester,(RS)-;Methyl (+)-(S)-alpha-(o-chlorophenyl)-6,7-dihydrothieno(3,2-c)pyridine-5(4H)-acetate;Clopidogrel (For R&D); |
| EINECS: | 601-269-2 |
| Density: | 1.317 g/cm3 |
| Boiling Point: | 423.7 °C at 760 mmHg |
| Flash Point: | 210 °C |
| Appearance: | white powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22-36/37/38 |
| Safety: | 26-36 |
| PSA: | 57.78000 |
| LogP: | 3.61180 |
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- 113665-84-2
(S)-(+)-clopidogrel
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate In dichloromethane; water Product distribution / selectivity; | 100% |
| With sodium hydrogencarbonate In dichloromethane; water at 15 - 20℃; pH=7 - 8; Product distribution / selectivity; | |
| With sodium hydrogencarbonate In chloroform; water for 2h; |
- 120202-66-6
(S)-(+)-clopidogrel bisulfate
- 113665-84-2
(S)-(+)-clopidogrel
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate In dichloromethane; water at 15℃; for 0.333333h; | 100% |
| With ammonia In hexane; water at 25 - 30℃; pH=7; | 97.86% |
| With sodium carbonate In dichloromethane; water at 20℃; for 0.5h; Large scale; | 92% |
- 909279-85-2
clopidogrel camphorsulfonate
- 113665-84-2
(S)-(+)-clopidogrel
| Conditions | Yield |
|---|---|
| With sodium carbonate In tert-butyl methyl ether; water at 20℃; for 0.5h; Solvent; | 100% |
| With sodium hydrogencarbonate In dichloromethane; water at 25 - 30℃; for 0.166667h; Product distribution / selectivity; | |
| With potassium carbonate In dichloromethane; water for 1h; pH=9; Product distribution / selectivity; cooling with cool salt water; |
- 113665-84-2
(S)-(+)-clopidogrel
| Conditions | Yield |
|---|---|
| With sodium carbonate In tert-butyl methyl ether; water for 0.5h; Solvent; | 100% |
| With sodium hydrogencarbonate In acetone for 6h; Reflux; |
- 113665-84-2
(S)-(+)-clopidogrel
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate In dichloromethane at 0 - 5℃; for 1h; | 99.2% |
| With potassium carbonate In dichloromethane; water for 0.5h; | 99% |
| With water; sodium hydrogencarbonate In dichloromethane at 0℃; Product distribution / selectivity; | 96% |
- 50-00-0
formaldehyd
- 113665-84-2
(S)-(+)-clopidogrel
| Conditions | Yield |
|---|---|
| at 40℃; for 4h; Darkness; | 98% |
| With hydrogenchloride In water at 20 - 80℃; for 2h; | 83.57% |
| Stage #1: (S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride; formaldehyd In water at 25 - 30℃; for 20 - 24h; Stage #2: With sodium carbonate In dichloromethane; water at 12 - 15℃; for 0.75 - 3.25h; pH=7.01 - 7.32; Product distribution / selectivity; |
- 28783-41-7
6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride
- 113665-84-2
(S)-(+)-clopidogrel
| Conditions | Yield |
|---|---|
| With sodium carbonate In dichloromethane at 25 - 40℃; for 24h; Temperature; | 97.02% |
| Conditions | Yield |
|---|---|
| Stage #1: SR 26334 With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at -10 - 0℃; for 2.5h; Stage #2: methanol In dichloromethane at 0 - 20℃; for 2.5h; | 96% |
| Stage #1: SR 26334; methanol With acetyl chloride Heating / reflux; Stage #2: With sodium hydroxide In water; ethyl acetate pH=7 - 8; Product distribution / selectivity; | 91% |
| Stage #1: SR 26334; methanol With thionyl chloride at 70℃; for 6h; Stage #2: With sodium hydrogencarbonate In water pH=7; Product distribution / selectivity; | 88% |
- 67-56-1
methanol
- 144750-42-5
(S)-(+)-2-(2-chlorophenyl)-2-(6,7-dihydrothieno-[3,2-c]pyridin-5(4H)-yl)acetic acid hydrochloride
- 113665-84-2
(S)-(+)-clopidogrel
| Conditions | Yield |
|---|---|
| Stage #1: (S)-(+)-2-(2-chlorophenyl)-2-(6,7-dihydrothieno-[3,2-c]pyridin-5(4H)-yl)acetic acid hydrochloride With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at -10 - 0℃; for 2.5h; Stage #2: methanol In dichloromethane at 0 - 20℃; for 2.5h; | 95% |
| Stage #1: methanol; (S)-(+)-2-(2-chlorophenyl)-2-(6,7-dihydrothieno-[3,2-c]pyridin-5(4H)-yl)acetic acid hydrochloride; sulfuric acid Heating / reflux; Stage #2: With sodium hydroxide In water; ethyl acetate pH=8; Product distribution / selectivity; | |
| Stage #1: methanol; (S)-(+)-2-(2-chlorophenyl)-2-(6,7-dihydrothieno-[3,2-c]pyridin-5(4H)-yl)acetic acid hydrochloride; sulfuric acid Heating / reflux; Stage #2: With calcium hydroxide; sodium hydroxide In water pH=8; Product distribution / selectivity; |
- 113665-84-2
(S)-(+)-clopidogrel
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate In dichloromethane pH=8; Conversion of starting material; | 95% |
| With potassium carbonate In dichloromethane; water pH=8; Conversion of starting material; |
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Specification
1. Introduction of Clopidogrel
Clopidogrel is one kind of white crystalline powder. The IUPAC Name of it is methyl(2S)-2-(2-chlorophenyl)-2-(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetate. Besides, it belongs to Cardiovascular;API;API's;Pharmaceutical intermediates. Its Classification Code is Hematologic Agents; Platelet Aggregation Inhibitors.
2. Properties of Clopidogrel
Physical properties about Clopidogrel are:
(1)Index of Refraction: 1.617; (2)Molar Refractivity: 85.48 cm3; (3)Molar Volume: 244.3 cm3; (4)Surface Tension: 52.7 dyne/cm; (5)Density: 1.317 g/cm3; (6)Flash Point: 210 °C; (7)Enthalpy of Vaporization: 67.81 kJ/mol; (8)Boiling Point: 423.7 °C at 760 mmHg; (9)Vapour Pressure of Clopidogrel: 2.19E-07 mmHg at 25 °C.
3. Structure Descriptors of Clopidogrel
(1)InChI: InChI=1S/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/m0/s1
(2)InChIKey: InChIKey=GKTWGGQPFAXNFI-HNNXBMFYSA-N
(3)Smiles: N1([C@@H](c2c(cccc2)Cl)C(=O)OC)Cc2c(CC1)scc2
4. Safety information of Clopidogrel
Hazard Codes: 
Xn
Risk Statements: 22-36/37/38
R22: Harmful if swallowed
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36: Wear suitable protective clothing
5. Uses of Clopidogrel
Clopidogrel is an oral, thienopyridine class antiplatelet agent used to inhibit blood clots in coronary artery disease, peripheral vascular disease, and cerebrovascular disease. It is also used, along with aspirin, for the prevention of thrombosis after placement of intracoronary stent or as an alternative antiplatelet drug for patients who are intolerant to aspirin. The drug works by irreversibly inhibiting a receptor called P2Y12, an adenosine diphosphate (ADP) chemoreceptor on platelet cell membranes. Adverse effects include hemorrhage, severe neutropenia, and thrombotic thrombocytopenic purpura (TTP).
6. Production of Clopidogrel
Racemic 2-(2-chlorophenyl)-glycine (I) in the hydrogen chloride, esterified with methanol to obtain racemic 2-(2-chlorophenyl) glycine methyl ester (II), and then (+)-tartaric acid split to obtain (+)-(II). Then thiophene and 2-(2-bromo-ethyl)-thiazole in methyl acetate, dipotassium hydrogen phosphate exists under alkylation; or 2-[2-(phenyl-sulfonyloxy) ethyl] thiophene in acetic acid methyl ester in the presence of sodium bicarbonate under alkylation, to obtain the compound (III). Finally obtain a clopidogrel from cyclized with formic acid and formaldehyde.