• Name

  6-(5-Chloro-2-pyridyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione

• EINECS 256-141-5
• CAS No. 43200-82-4
• Article Data9
• CAS DataBase
• Density 1.645 g/cm³
• Solubility
• Melting Point 238 °C
• Formula C₁₁H₅ClN₄O₂
• Boiling Point 495.7 °C at 760 mmHg
• Molecular Weight 260.639
• Flash Point 253.6 °C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 6-(5-chloro-2-pyridyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione;
• PSA 76.05000
• LogP 1.39060

Synthetic route

32315-10-9

bis(trichloromethyl) carbonate

43200-83-5

3-((5-chloropyridin-2-yl)carbamoyl)pyrazine-2-carboxylic acid

43200-82-4

6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

Conditions

Conditions	Yield
With Triphenylphosphine oxide In dichloromethane at 20℃; for 0.0833333h; Temperature; Concentration;	98.5%

1072-98-6

5-chloro-2-pyridylamine

4744-50-7

2,3-pyrazinedicarboxylic anhydride

43200-82-4

6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

Conditions

Conditions	Yield
With propionic acid anhydride at 60 - 105℃; for 1h; Temperature; Reagent/catalyst;	87%
With dmap; triethylamine In 5,5-dimethyl-1,3-cyclohexadiene at 0℃; for 13h; Reflux;	85%

43200-83-5

3-((5-chloropyridin-2-yl)carbamoyl)pyrazine-2-carboxylic acid

43200-82-4

6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

Conditions

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0 - 20℃; for 2h;
Stage #1: 3-((5-chloropyridin-2-yl)carbamoyl)pyrazine-2-carboxylic acid In dichloromethane for 1h; Heating / reflux; Stage #2: With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 25 - 30℃; for 0.75 - 1h; Heating / reflux;

(7S)-6-(5-chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one

43200-82-4

6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

Conditions

Conditions	Yield
With manganese(IV) oxide In dichloromethane for 3h; Reflux;	12.5 g

1072-98-6

5-chloro-2-pyridylamine

43200-82-4

6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene / 2.5 h / 20 - 52 °C 1.2: 1 h / 10 - 15 °C 2.1: dichloromethane / 1 h / Heating / reflux 2.2: 0.75 - 1 h / 25 - 30 °C / Heating / reflux View Scheme

4744-50-7

2,3-pyrazinedicarboxylic anhydride

43200-82-4

6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: toluene / 2.5 h / 20 - 52 °C 1.2: 1 h / 10 - 15 °C 2.1: dichloromethane / 1 h / Heating / reflux 2.2: 0.75 - 1 h / 25 - 30 °C / Heating / reflux View Scheme

43200-82-4

6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

148891-53-6

6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
With diisobutylaluminium hydride In toluene at -25 - -10℃; for 2h; Temperature; Solvent;	91.1%

43200-82-4

6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

43200-81-3

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
Stage #1: 6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine With potassium borohydride In 1,4-dioxane at 10 - 15℃; for 0.5h; Stage #2: With water In 1,4-dioxane for 6h;	87.4%
With potassium borohydride; water In tetrahydrofuran at -10 - 5℃; for 3h; Large scale;	70%
With potassium borohydride; potassium carbonate In 1,4-dioxane; water; N,N-dimethyl-formamide at 13℃; pH=11; Reagent/catalyst; Solvent; pH-value;	95.5 g
With sodium hydroxide; sodium tetrahydroborate In water at 0 - 5℃; for 4 - 5h; Product distribution / selectivity;

43200-82-4

6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

144025-94-5

(R)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate D-(+)-O,O'-dibenzoyltartaric acid salt

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; sodium tetrahydroborate / water / 4 - 5 h / 0 - 5 °C 2: dmap; calcium oxide / dichloromethane; N,N-dimethyl-formamide / 10 - 30 °C 3: water; acetonitrile / 3 - 4.5 h / 25 - 80 °C / Resolution of racemate View Scheme

43200-82-4

6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

144025-93-4

eszopiclone dibenzoyl-D-tartrate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; sodium tetrahydroborate / water / 4 - 5 h / 0 - 5 °C 2: dmap; calcium oxide / dichloromethane; N,N-dimethyl-formamide / 10 - 30 °C 3: water; acetonitrile / 3 - 4.5 h / 25 - 80 °C / Resolution of racemate View Scheme

43200-82-4

6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

138729-47-2

eszopiclone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydroxide; sodium tetrahydroborate / water / 4 - 5 h / 0 - 5 °C 2: dmap; calcium oxide / dichloromethane; N,N-dimethyl-formamide / 10 - 30 °C 3: water; acetonitrile / 3 - 4.5 h / 25 - 80 °C / Resolution of racemate 4: water; sodium hydrogencarbonate / 3 - 4 h / 25 - 30 °C View Scheme