| Identification | Back Directory | [Name]
CLOPIDOGREL RELATED COMPOUND A (20 MG) ((S)-(O-CHLOROPHENYL)-6,7-DIHYDROTHIENO[3,2-C]PYRI-DINE-5(4H)-ACETIC ACID, HYDROCHLORIDE) | [CAS]
144750-42-5 | [Synonyms]
Clopidogrel USP RC A
Clopidogrel EP IMpurity-A
Clopidogrel Impurity A（EP）
Clopidogrel EP Impurity A HCl
Clopidogrel Related CoMpound A
Clopidogrel acid hydrochloride
Clopidogrel-related impurities A
Clopidogrel USP Related CoMpound A
Clopidogrel carboxylic acid Impurity
Clopidogrel EP impurity-A (USP RC A)
Clopidogrel Related Compound A (H0M124)
Clopidogrel Carboxylic Acid Hydrochloride
Clopidogrel Carboxylic Acid Hydrochloride Salt
Clopidogrel Related Compound A as Hydrochloride
Clopidogrel USP Related Compound A as Hydrochloride
Clopidogrel Hydrogen Sulfate Impurity A as Hydrochloride
Clopidogrel Impurity 1 HCl(Clopidogrel EP Impurity A HCl)
Clopidogrel Hydrogen Sulfate EP Impurity A as Hydrochloride
(S)-(2-Chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetic acid hydrochloride
(S)-(o-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetic acid, hydrochloride
alpha-(2-Chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-acetic acid hydrochloride
(+)-(S)-(o-Chlorophenyl)-6,7-dihydrothieno3,2-cpyridine-5(4H)-acetic acid hydrochloride
(S)-2-(2-Chlorophenyl)-2-(6,7-dihydrothieno-[3,2-c]pyridin-5(4H)-yl)acetic acid hydrochloride
Thieno[3,2-c]pyridine-5(4H)-acetic acid, α-(2-chlorophenyl)-6,7-dihydro-, hydrochloride (1:1), (αS)-
Thieno[3,2-c]pyridine-5(4H)-acetic acid, α-(2-chlorophenyl)-6,7-dihydro-, hydrochloride (1:1), (αS)-
Clopidogrel Related Compound A ((+)-(S)-(o-chlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-ace (1140586)
(S)-2-(2-chlorophenyl)-2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetic acid hydrochloride? (Clopidogrel Impurity）
Clopidogrel Related Compound A (20 mg) ((S)-(ochlorophenyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-aceticv acid, hydrochloride)
CLOPIDOGREL RELATED COMPOUND A (20 MG) ((S)-(O-CHLOROPHENYL)-6,7-DIHYDROTHIENO[3,2-C]PYRI-DINE-5(4H)-ACETIC ACID, HYDROCHLORIDE)
CLOPIDOGREL RELATED COMPOUND A (20 MG) ((S)-(O-CHLOROPHENYL)-6,7-DIHYDROTHIENO[3,2-C]PYRI-DINE-5(4H)-ACETIC ACID, HYDROCHLORIDE)
Clopidogrel Impurity 2/Clopidogrel EP Impurity A HCl/(S)-Clopidogrel Acid Hydrochloride/(S)-2-(2-Chlorophenyl)-2-(6,7-dihydrothieno-[3,2-c]pyridin-5(4H)-yl)acetic acid hydrochloride | [Molecular Formula]
C15H14ClNO2S.ClH | [MDL Number]
MFCD08063656 | [MOL File]
144750-42-5.mol | [Molecular Weight]
344.26 |
| Chemical Properties | Back Directory | [Melting point ]
147-155°C (dec.) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
neat | [color ]
Off-White to Pale Yellow | [Optical Rotation]
49.64°(C=0.164g/100mI, MEOH, 20°C, 589nm) | [Stability:]
Hygroscopic | [Major Application]
pharmaceutical | [InChI]
1S/C15H14ClNO2S.ClH/c16-12-4-2-1-3-11(12)14(15(18)19)17-7-5-13-10(9-17)6-8-20-13;/h1-4,6,8,14H,5,7,9H2,(H,18,19);1H/t14-;/m0./s1 | [InChIKey]
FOKSIOUPGDBSLC-UQKRIMTDSA-N | [SMILES]
Cl.OC(=O)[C@@H](N1CCc2sccc2C1)c3ccccc3Cl |
| Hazard Information | Back Directory | [Uses]
Clopidogrel Carboxylic Acid Hydrochloride (Clopidogrel EP Impurity A; Clopidogrel Impurity A; Clopidogrel USP A) is the hydrochloride salt of a metabolite of the drug Clopidogrel. | [Synthesis]
Example 6: Preparation of (S)-(+)-α-(2-chlorophenyl)-6,7-dihydro-4H-thieno[3,2-c]pyridine-5-acetic acid hydrochloride (Formula (III) hydrochloride)
1. 61 g of (S)-(+)-α-(2-chlorophenyl)-6,7-dihydro-4H-thieno[3,2-c]pyridine-5-acetic acid (the product of Example 5) was dissolved in a solvent mixture of 300 mL of acetone and 15 mL of methanol, and was heated to 40° C. to dissolve completely.
2. 16.4 mL of concentrated hydrochloric acid was slowly added to the above solution, after which the reaction mixture was stirred continuously at room temperature for 2 hours.
3. the reaction mixture was cooled to below 5 °C and kept at this temperature for at least 2 hours to promote crystallization.
4. The precipitated crystals were collected by filtration, washed with 100 mL of cold acetone and subsequently dried under reduced pressure at 40 °C to afford 61 g of the title compound as a white to pale yellow solid (yield: 90%).
Product Characterization.
- Melting point: 200-201°C
- Spin: [α]D20 +64.87° (c=1%, MeOH)
- Optical purity: 99.5% ee (HPLC)
- 1H-NMR (DMSO-d6, ppm): δ 3.10 (s, 3H), 3.47 (s, 2H), 4.30 (s, 2H), 5.54 (s, 1H), 6.91 (d, 1H, J=4.8Hz), 7.44 (d, 1H, J=4.8Hz), 7.46-7.58 (m, 2H), 7.65 (d, 1H, J=7.4Hz), 7.65 (d, 1H, J=7.4Hz), 7.65 (d, 1H, J=7.4Hz). J=7.4 Hz), 7.97 (d, 1H, J=7.1 Hz)
- 13C-NMR (DMSO-d6, ppm): δ 21.78, 48.81, 50.17, 65.43, 125.04, 125.54, 127.99, 128.29, 128.36, 130.37, 130.46, 131.49, 132.02, 134.43, 167.53
- IR (KBr, cm-1): 3435, 3114, 1728 | [References]
[1] Patent: US2008/214821, 2008, A1. Location in patent: Page/Page column 5
[2] Patent: WO2006/137628, 2006, A1. Location in patent: Page/Page column 13 |
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