| Identification | More | [Name]
5-CHLORO-PYRAZINE-2-CARBOXYLIC ACID | [CAS]
36070-80-1 | [Synonyms]
5-CHLORO-PYRAZINE-2-CARBOXYLIC ACID
5-Chloro-2-pyrazinecarboxylic acid
5-chloro-pyrazin-5-carboxylic acid
5-CHLORO-2-PYRAZINECARBOXYLICACID(MFCD00190599)
5-chloropyrazine-2-carboxlic acid
5-Chlopopyrazine-2-carboxylic acid | [EINECS(EC#)]
636-844-7 | [Molecular Formula]
C5H3ClN2O2 | [MDL Number]
MFCD09033269 | [Molecular Weight]
158.543 | [MOL File]
36070-80-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
150-151℃ | [Boiling point ]
330.9±37.0 °C(Predicted) | [density ]
1.579±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
2.68±0.10(Predicted) | [color ]
White to Light yellow | [InChI]
InChI=1S/C5H3ClN2O2/c6-4-2-7-3(1-8-4)5(9)10/h1-2H,(H,9,10) | [InChIKey]
FXJOTWLLDJYKAG-UHFFFAOYSA-N | [SMILES]
C1(C(O)=O)=NC=C(Cl)N=C1 | [CAS DataBase Reference]
36070-80-1(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
5-Chloropyrazine-2-carboxylic acid | [Synthesis]
Example 29: Synthesis of 5-[2(R)-(3-chloro-4-methylsulfonyl-phenyl)-3-cyclopentylpropylamino]-pyrazine-2-carboxylic acid hydroxylamides [000197] General steps:
1. dissolve methyl 5-chloropyrazine-2-carboxylate (30.00 g, 0.17 mol) in tetrahydrofuran (87 mL).
2. a solution of potassium carbonate (72.08 g, 0.52 mol) in water (261 mL) was added to the above solution.
3. The reaction mixture was stirred at 25 °C for 42 h. 4.
4. Upon completion of the reaction, the reaction mixture was acidified to a pH of about 2 with concentrated hydrochloric acid.
5. The reaction mixture was diluted with saturated aqueous sodium chloride solution (300 mL).
6. Extracted successively with ethyl acetate (4 L total) until no product was detected in the aqueous layer.
7. The organic layers were combined, dried over sodium sulfate and filtered.
8. The filtrate was concentrated in vacuum to give 5-chloropyrazine-2-carboxylic acid (26.54 g, 96% yield) as an off-white solid.
Physical properties: melting point 150-151°C; EH-HRMS m/e calculated value C5H3ClN2O2 (M+) 157.9883, measured value 157.9877. | [References]
[1] Patent: WO2004/52869, 2004, A1. Location in patent: Page 115 - 116
[2] Patent: WO2006/66173, 2006, A2. Location in patent: Page/Page column 71-72
[3] Patent: US2010/210621, 2010, A1
[4] Patent: US2010/210841, 2010, A1. Location in patent: Page/Page column 18
[5] Organic Process Research and Development, 2017, vol. 21, # 3, p. 346 - 356 |
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