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6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one
Cas No: 43200-81-3
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High quality 6-(5-chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one with best price cas:43200-81-3
Cas No: 43200-81-3
USD $ 250.0-350.0 / Kilogram 1 Kilogram 99999 Kilogram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one
Cas No: 43200-81-3
USD $ 12.0-12.0 / Gram 100 Gram 50 Metric Ton/Year Jinan Finer Chemical Co., Ltd Contact Supplier
6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one
Cas No: 43200-81-3
No Data 1 Kilogram 20 Metric Ton/Day Henan Allgreen Chemical Co.,Ltd Contact Supplier
Factory Supply 6-(5-chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one
Cas No: 43200-81-3
No Data 1 1 Ality Chemical Corporation Contact Supplier
6-(5-chloro-2-pyridinyl)-7-hydroxy-7H-pyrrolo[3,4-b]pyrazin-5-one
Cas No: 43200-81-3
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier
6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one
Cas No: 43200-81-3
No Data 1 Kilogram 10 Metric Ton/Month Henan Tianfu Chemical Co., Ltd. Contact Supplier
6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one CAS NO 43200-81-3
Cas No: 43200-81-3
No Data 1 Kilogram 20000 Kilogram/Day Hubei XinRunde Chemical Co., Ltd Contact Supplier
Pharmaceutical Grade CAS 43200-81-3 with competitive price
Cas No: 43200-81-3
USD $ 139.0-210.0 / Kilogram 1 Kilogram 1000 Kilogram/Day Zhuozhou Wenxi import and Export Co., Ltd Contact Supplier
BLOOM TECH Advanced API/Technology support 6-(5-Chloro-2-pyridyl)-6;7-dihydro-7-hydroxy-5H-pyrrolo[3;4-b]pyrazin-5-one CAS 43200-81-3
Cas No: 43200-81-3
No Data 1 Gram 3 Metric Ton/Month Shaanxi BLOOM TECH Co.,Ltd Contact Supplier

43200-81-3 Usage

Chemical Properties

Yellow Crystalline Powder

Uses

Eszopiclone intermediate

Uses

Eszopiclone Impurity B.
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

43200-81-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (Y0001822)  Zopiclone impurity B  EuropePharmacopoeia (EP) Reference Standard 43200-81-3 Y0001822 1,880.19CNY Detail

43200-81-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names Intermediate for Zopiclone II

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:43200-81-3 SDS

43200-81-3Synthetic route

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

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

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

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

Conditions
ConditionsYield
With sulfuric acid In ethanol for 3h; Reflux;88.7%
6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine
43200-82-4

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

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

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

Conditions
ConditionsYield
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;
(-)-Zopiclone
138680-08-7

(-)-Zopiclone

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

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

Conditions
ConditionsYield
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;
(+/-)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-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

A

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

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

B

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

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

Conditions
ConditionsYield
With phosphate buffer; Candida antarctica lipase B Chirazyme-L2; triethylamine In water; toluene at 60℃; for 96h; pH=7;
(+/-)-7-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-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

A

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

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

B

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

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

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

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

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

Conditions
ConditionsYield
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;
(+/-)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-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

A

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

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

B

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

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

C

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

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

Conditions
ConditionsYield
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
2,3-pyrazinedicarboxylic anhydride
4744-50-7

2,3-pyrazinedicarboxylic anhydride

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

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

Conditions
ConditionsYield
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
5-chloro-2-pyridylamine
1072-98-6

5-chloro-2-pyridylamine

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

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

Conditions
ConditionsYield
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
zopiclon
43200-80-2

zopiclon

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

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

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

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

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

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

Conditions
ConditionsYield
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
2-Chloroethyl chloroformate
627-11-2

2-Chloroethyl chloroformate

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

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

(+/-)-7-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-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
ConditionsYield
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;
carbonochloridic acid 1-chloro-ethyl ester
50893-53-3

carbonochloridic acid 1-chloro-ethyl ester

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

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

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 4h;98%
With pyridine
2,2,2-trichloro-1,1-dimethylethoxychloroformate
66270-36-8

2,2,2-trichloro-1,1-dimethylethoxychloroformate

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

(+/-)-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
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 2h;98%
With pyridine
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one
43200-81-3

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

2,2,2-Trichloroethyl chloroformate
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

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

Conditions
ConditionsYield
With pyridine In dichloromethane at 25℃; for 5h;98%
With pyridine In dichloromethane at 0 - 20℃; for 5h;98%
4-methylpiperazine-1-carbonyl chloride monohydrochloride
55112-42-0

4-methylpiperazine-1-carbonyl chloride monohydrochloride

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

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

zopiclon
43200-80-2

zopiclon

Conditions
ConditionsYield
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%
Isopropenyl chloroformate
57933-83-2

Isopropenyl chloroformate

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one
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-(2-propenyloxycarbonyloxy)-5,6-dihydropyrrolo[3,4b]pyrazine
862210-86-4

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

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 6h;93%
6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one
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)-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
ConditionsYield
With diisobutylaluminium hydride In toluene at -15℃; for 2h; Temperature;92.6%
benzoyl chloride
98-88-4

benzoyl chloride

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

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

Conditions
ConditionsYield
With pyridine In dichloromethane at 25℃; for 4h;89%
butyryl chloride
141-75-3

butyryl chloride

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

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

Conditions
ConditionsYield
With pyridine In dichloromethane at 25℃; for 5h;87%
carbonochloridic acid, chloromethyl ester
22128-62-7

carbonochloridic acid, chloromethyl ester

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

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

(+/-)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-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
ConditionsYield
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%
acetyl chloride
75-36-5

acetyl chloride

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

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

Conditions
ConditionsYield
With pyridine In dichloromethane at 25℃; for 5h;85%
4-methyl-piperazine-1-carbonyl chloride
39539-66-7

4-methyl-piperazine-1-carbonyl chloride

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

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

zopiclon
43200-80-2

zopiclon

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

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

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

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

Conditions
ConditionsYield
With sodium tetrahydroborate In 1,4-dioxane; water at 10 - 15℃; for 2h;75.2%
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one
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-(vinyloxycarbonyloxy)-5,6-dihydropyrrolo[3,4b]pyrazine
190369-20-1

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

Conditions
ConditionsYield
With pyridine In dichloromethane at 25℃; for 10h;75%
4-Nitrophenyl chloroformate
7693-46-1

4-Nitrophenyl chloroformate

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

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

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 21h;55%
With pyridine
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

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

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

Conditions
ConditionsYield
With pyridine; triethylamine In acetonitrile at 0 - 20℃; for 18h;40%
phenyl chloroformate
1885-14-9

phenyl chloroformate

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

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

C18H11ClN4O4

C18H11ClN4O4

Conditions
ConditionsYield
With (R)-6-benzyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole; triethylamine In dichloromethane at 20℃; Catalytic behavior; enantioselective reaction;35%
2-nitrophenyl chloroformate
50353-00-9

2-nitrophenyl chloroformate

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

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

Conditions
ConditionsYield
With pyridine
carbonochloridic acid, chloromethyl ester
22128-62-7

carbonochloridic acid, chloromethyl ester

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

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

A

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

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

Conditions
ConditionsYield
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;
2-Chloroethyl chloroformate
627-11-2

2-Chloroethyl chloroformate

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

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

A

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

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

Conditions
ConditionsYield
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;
acetyl chloride
75-36-5

acetyl chloride

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

(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

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

Conditions
ConditionsYield
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;
butyryl chloride
141-75-3

butyryl chloride

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

(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

(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

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

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

Conditions
ConditionsYield
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;
Vinyl chloroformate
5130-24-5

Vinyl chloroformate

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

(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

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

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

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

eszopiclone
138729-47-2

eszopiclone

Conditions
ConditionsYield
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
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