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

Name
6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one
EINECS 256-139-4
CAS No. 43200-81-3
Article Data13
CAS DataBase
Density 1.653 g/cm³
Solubility
Melting Point 240.5-241.5 °C
Formula C₁₁H₇ClN₄O₂
Boiling Point 525.2 °C at 760 mmHg
Molecular Weight 262.655
Flash Point 271.5 °C
Transport Information
Appearance Yellow crystalline powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 6-(5-Chloropyrid-2-yl)-5-hydroxy-7-oxo-5,6-dihydropyrrolo[3,4-b]pyrazine;RP29307;5H-Pyrrolo[3,4-b]pyrazin-5-one,6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-hydroxy-;
PSA 79.21000
LogP 1.24130

Synthetic route

: 6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3.4-b]pyrazin-5-yl acetate

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
With sulfuric acid In ethanol for 3h; Reflux;	88.7%

: 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;

: 138680-08-7
(-)-Zopiclone

: 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: (-)-Zopiclone With trifluoroacetic acid In dichloromethane for 18h; Heating / reflux; Stage #2: With water; sodium hydrogencarbonate In dichloromethane at 0℃; pH=7.5 - 8; Product distribution / selectivity;	70%
Stage #1: (-)-Zopiclone With trifluoroacetic acid In dichloromethane for 18h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In dichloromethane; water at 0℃; pH=7.5 - 8; Product distribution / selectivity;	70%
Stage #1: (-)-Zopiclone With hydrogenchloride; water In methanol at 41℃; for 11h; Stage #2: With sodium hydrogencarbonate In methanol; water at 10 - 15℃; Product distribution / selectivity;	41.24%
Stage #1: (-)-Zopiclone With hydrogenchloride; water In methanol at 41℃; for 11h; Stage #2: With sodium hydrogencarbonate In methanol; water at 10 - 15℃; Product distribution / selectivity;	41.24%
With hydrogenchloride; water at 70℃; for 3h;

: 508169-18-4
(+/-)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

A: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

B: 508169-20-8
(S)-(+)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
With phosphate buffer; Candida antarctica lipase B Chirazyme-L2; triethylamine In water; toluene at 60℃; for 96h; pH=7;

: 508169-17-3
(+/-)-7-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

A: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

B: 508169-19-5
(S)-(+)-7-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
With phosphate buffer; Candida antarctica lipase B Novozym 435 In water; toluene at 60℃; for 96h; pH=7;

: 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

: 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: (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 With water; sodium hydrogencarbonate In dichloromethane; acetonitrile at 25 - 30℃; for 0.75h; Stage #2: With hydrogenchloride; formic acid; water at 0 - 68℃; for 4h; Product distribution / selectivity;

: 508169-18-4
(+/-)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

A: 1151528-25-4
(R)-5-(chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-7-oxo-5,6-dihydropyrrolo[3,4-b]pyrazine

B: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

C: 508169-20-8
(S)-(+)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
With propan-1-ol; triethylamine; Novozyme 435 In toluene at 45℃; for 16 - 24h; Purification / work up; Enzymatic reaction; Resolution of racemate;	A n/a B n/a C n/a

...Expand

: 4744-50-7
2,3-pyrazinedicarboxylic anhydride

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dmap; triethylamine / 5,5-dimethyl-1,3-cyclohexadiene / 13 h / 0 °C / Reflux 2.1: potassium borohydride / 1,4-dioxane / 0.5 h / 10 - 15 °C 2.2: 6 h View Scheme
Multi-step reaction with 3 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 3.1: sodium hydroxide; sodium tetrahydroborate / water / 4 - 5 h / 0 - 5 °C View Scheme
Multi-step reaction with 2 steps 1: propionic acid anhydride / 1 h / 60 - 105 °C 2: potassium borohydride; water / tetrahydrofuran / 3 h / -10 - 5 °C / Large scale View Scheme

: 1072-98-6
5-chloro-2-pyridylamine

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dmap; triethylamine / 5,5-dimethyl-1,3-cyclohexadiene / 13 h / 0 °C / Reflux 2.1: potassium borohydride / 1,4-dioxane / 0.5 h / 10 - 15 °C 2.2: 6 h View Scheme
Multi-step reaction with 3 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 3.1: sodium hydroxide; sodium tetrahydroborate / water / 4 - 5 h / 0 - 5 °C View Scheme
Multi-step reaction with 3 steps 1: isopropyl alcohol / 5 h / Reflux; Large scale 2: 1 h / Reflux; Large scale 3: sulfuric acid / ethanol / 3 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: propionic acid anhydride / 1 h / 60 - 105 °C 2: potassium borohydride; water / tetrahydrofuran / 3 h / -10 - 5 °C / Large scale View Scheme

: 43200-80-2
zopiclon

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: water; acetonitrile / 3 - 4.5 h / 25 - 80 °C / Resolution of racemate 2.1: water; sodium hydrogencarbonate / dichloromethane; acetonitrile / 0.75 h / 25 - 30 °C 2.2: 4 h / 0 - 68 °C View Scheme

: 43200-83-5
3-((5-chloropyridin-2-yl)carbamoyl)pyrazine-2-carboxylic acid

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dichloromethane / 1 h / Heating / reflux 1.2: 0.75 - 1 h / 25 - 30 °C / Heating / reflux 2.1: sodium hydroxide; sodium tetrahydroborate / water / 4 - 5 h / 0 - 5 °C View Scheme

: 627-11-2
2-Chloroethyl chloroformate

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: 508169-17-3
(+/-)-7-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
With pyridine In dichloromethane at 25℃; for 7h;	98%
With pyridine In dichloromethane at 0 - 20℃; for 7h;	98%
With pyridine In dichloromethane at 20℃; for 7h;

: 50893-53-3
carbonochloridic acid 1-chloro-ethyl ester

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: (+/-)-7-(1-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 4h;	98%
With pyridine

: 66270-36-8
2,2,2-trichloro-1,1-dimethylethoxychloroformate

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: (+/-)-7-(1,1-dimethyl-2,2,2-trichloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 2h;	98%
With pyridine

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: (+/-)-6-(5-chloropyridin-2-yl)-7-oxo-5-(2,2,2-trichloroethyloxycarbonyloxy)-5,6-dihydropyrrolo[3,4b]pyrazine

Conditions

Conditions	Yield
With pyridine In dichloromethane at 25℃; for 5h;	98%
With pyridine In dichloromethane at 0 - 20℃; for 5h;	98%

: 55112-42-0
4-methylpiperazine-1-carbonyl chloride monohydrochloride

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: 43200-80-2
zopiclon

Conditions

Conditions	Yield
Stage #1: 4-methylpiperazine-1-carbonyl chloride monohydrochloride With triethylamine In dichloromethane at 5℃; for 0.416667h; Stage #2: dmap In dichloromethane for 0.0166667 - 0.0333333h; Stage #3: 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one In dichloromethane at 20℃; for 7h; Product distribution / selectivity; Heating / reflux;	95%
With triethylamine; dmap In 2-methylpropyl acetate at 80℃; for 5.5h; Product distribution / selectivity;	91.7%
Stage #1: 4-methylpiperazine-1-carbonyl chloride monohydrochloride With triethylamine In ethyl acetate for 0.166667h; Stage #2: 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one; dmap In ethyl acetate at 60℃; for 7.5h; Product distribution / selectivity;	90%

: 57933-83-2
Isopropenyl chloroformate

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: 862210-86-4
6-(5-chloropyridin-2-yl)-7-oxo-5-(2-propenyloxycarbonyloxy)-5,6-dihydropyrrolo[3,4b]pyrazine

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 6h;	93%

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: 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 -15℃; for 2h; Temperature;	92.6%

: 98-88-4
benzoyl chloride

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: benzoic acid 6-(5-chloro-pyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at 25℃; for 4h;	89%

: 141-75-3
butyryl chloride

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: butyric acid 6-(5-chloro-pyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at 25℃; for 5h;	87%

: 22128-62-7
carbonochloridic acid, chloromethyl ester

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: 508169-18-4
(+/-)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 17h;	86%
With pyridine In dichloromethane at 25℃; for 17h;	86%
With pyridine In dichloromethane at 0 - 20℃; for 17h;	86%

: 75-36-5
acetyl chloride

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: 6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3.4-b]pyrazin-5-yl acetate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 25℃; for 5h;	85%

: 39539-66-7
4-methyl-piperazine-1-carbonyl chloride

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: 43200-80-2
zopiclon

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 3h; Reflux;	80%
With dmap; triethylamine In acetonitrile at 60 - 65℃; for 1.5h; Large scale;	80.9%
Stage #1: 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at -10 - 35℃; Stage #2: 4-methyl-piperazine-1-carbonyl chloride In N,N-dimethyl-formamide; mineral oil at -10 - 20℃; Product distribution / selectivity;	78.81%
Stage #1: 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one With sodium hydride In N,N-dimethyl-formamide at -10℃; Stage #2: 4-methyl-piperazine-1-carbonyl chloride In N,N-dimethyl-formamide at -10 - 20℃; for 3h; Product distribution / selectivity;	78.81%
With sodium hydride In N,N-dimethyl-formamide Product distribution / selectivity;

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: 1122549-43-2
3-hydroxymethyl-pyrazine-2-carboxylic acid N-(5-chloro-pyridin-2-yl)-amide

Conditions

Conditions	Yield
With sodium tetrahydroborate In 1,4-dioxane; water at 10 - 15℃; for 2h;	75.2%

: 5130-24-5
Vinyl chloroformate

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: 190369-20-1
(+/-)-6-(5-chloropyridin-2-yl)-7-oxo-5-(vinyloxycarbonyloxy)-5,6-dihydropyrrolo[3,4b]pyrazine

Conditions

Conditions	Yield
With pyridine In dichloromethane at 25℃; for 10h;	75%

: 7693-46-1
4-Nitrophenyl chloroformate

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

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

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 21h;	55%
With pyridine

: 74124-79-1
di(succinimido) carbonate

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: 6-(5-chloropyridin-2-yl)-7-oxo-5-(N-succinimidyloxycarbonyloxi)-5,6-dihydropyrrolo[3,4b]pyrazine

Conditions

Conditions	Yield
With pyridine; triethylamine In acetonitrile at 0 - 20℃; for 18h;	40%

: 1885-14-9
phenyl chloroformate

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: C18H11ClN4O4

Conditions

Conditions	Yield
With (R)-6-benzyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole; triethylamine In dichloromethane at 20℃; Catalytic behavior; enantioselective reaction;	35%

: 50353-00-9
2-nitrophenyl chloroformate

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

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

Conditions

Conditions	Yield
With pyridine

: 22128-62-7
carbonochloridic acid, chloromethyl ester

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

A: 508169-20-8
(S)-(+)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

B: (R)-6-(5-chloropyridin-2-yl)-5-hydroxy-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine

Conditions

Conditions	Yield
Stage #1: carbonochloridic acid, chloromethyl ester; 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one With pyridine In dichloromethane at 25℃; for 17h; Stage #2: With Candida antarctica lipase (fraction B) - octadecyl-Sepabeads; sodium phosphate In 1,4-dioxane; water at 25℃; pH=7;

...Expand

: 627-11-2
2-Chloroethyl chloroformate

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

A: 508169-19-5
(S)-(+)-7-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

B: (R)-6-(5-chloropyridin-2-yl)-5-hydroxy-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine

Conditions

Conditions	Yield
Stage #1: 2-Chloroethyl chloroformate; 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one With pyridine In dichloromethane at 25℃; for 7h; Stage #2: With Candida antarctica lipase (fraction B) - octadecyl-Sepabeads; sodium phosphate In 1,4-dioxane; water at 25℃; pH=7;

...Expand

: 75-36-5
acetyl chloride

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

A: (R)-6-(5-chloropyridin-2-yl)-5-hydroxy-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine

B: acetic acid 6-(5-chloro-pyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl ester

Conditions

Conditions	Yield
Stage #1: acetyl chloride; 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one With pyridine In dichloromethane at 25℃; for 5h; Stage #2: With Candida antarctica lipase (fraction B) - octadecyl-Sepabeads; sodium phosphate In 1,4-dioxane; water at 37℃; pH=7;

...Expand

: 141-75-3
butyryl chloride

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

A: (R)-6-(5-chloropyridin-2-yl)-5-hydroxy-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine

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

C: butyric acid 6-(5-chloro-pyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl ester

D: butyric acid 6-(5-chloro-pyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl ester

Conditions

Conditions	Yield
Stage #1: butyryl chloride; 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one With pyridine In dichloromethane at 25℃; for 5h; Stage #2: With Candida antarctica lipase (fraction B) - octadecyl-Sepabeads; sodium phosphate In 1,4-dioxane; water at 25℃; pH=7; Title compound not separated from byproducts;

...Expand

: 5130-24-5
Vinyl chloroformate

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

A: (R)-6-(5-chloropyridin-2-yl)-5-hydroxy-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine

B: (S)-6-(5-chloropyridin-2-yl)-7-oxo-5-(vinyloxycarbonyloxy)-5,6-dihydropyrrolo[3,4b]pyrazine

Conditions

Conditions	Yield
Stage #1: Vinyl chloroformate; 6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one With pyridine In dichloromethane at 25℃; for 10h; Stage #2: With Candida antarctica lipase (fraction B) - octadecyl-Sepabeads; sodium phosphate In 1,4-dioxane; water at 25℃; pH=7;

...Expand

: 43200-81-3
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

: 138729-47-2
eszopiclone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / pyridine / CH2Cl2 / 17 h / 20 °C 2: Candida antarctica lipase B Chirazyme-L2; phosphate buffer; triethylamine / toluene; H2O / 96 h / 60 °C / pH 7 3: 90 percent / acetone / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: (R)-6-tert-butyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole; triethylamine / dichloromethane / 0 °C 2: acetonitrile / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: dmap; calcium oxide / dichloromethane; N,N-dimethyl-formamide / 10 - 30 °C 2: water; acetonitrile / 3 - 4.5 h / 25 - 80 °C / Resolution of racemate 3: water; sodium hydrogencarbonate / 3 - 4 h / 25 - 30 °C View Scheme

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

IUPAC Name: 6-(5-Chloropyridin-2-yl)pyrrolo[3,4-b]pyrazine-5,7-dione
Synonyms of 6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one (CAS NO.43200-81-3): 5H-Pyrrolo[3,4-b]pyrazin-5-one,6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-hydroxy-
CAS NO: 43200-81-3
Molecular Formula: C₁₁H₇ClN₄O₂
Molecular Weight: 262.65
Molecular Structure:
EINECS: 256-139-4
H bond acceptors: 6
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 68.21 Å²
Index of Refraction: 1.719
Molar Refractivity: 62.71 cm³
Molar Volume: 158.8 cm³
Surface Tension: 95.4 dyne/cm
Density: 1.653 g/cm³
Flash Point: 271.5 °C
Enthalpy of Vaporization: 84.14 kJ/mol
Boiling Point: 525.2 °C at 760 mmHg
Vapour Pressure: 7.35E-12 mmHg at 25 °C
Appearance: Yellow Crystalline Powder
SMILES: Clc1ccc(nc1)N3C(=O)c2nccnc2C3O
InChI: InChI=1/C11H7ClN4O2/c12-6-1-2-7(15-5-6)16-10(17)8-9(11(16)18)14-4-3-13-8/h1-5,10,17H
InChIKey: FUUXOEKDNNWZTR-UHFFFAOYAP
Std. InChI: InChI=1S/C11H7ClN4O2/c12-6-1-2-7(15-5-6)16-10(17)8-9(11(16)18)14-4-3-13-8/h1-5,10,17H
Std. InChIKey: FUUXOEKDNNWZTR-UHFFFAOYSA-N
Product Categories of 6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one (CAS NO.43200-81-3): Aromatics Compounds; Aromatics; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals

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

6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one (CAS NO.43200-81-3) is used as Eszopiclone intermediate.

Product Name

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

Synthetic route

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

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

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