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6628-77-9

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6628-77-9 Usage

Chemical Properties

yellow-brown or red to very dark red liquid

Uses

5-Amino-2-methoxypyridine is used as a reagent in the synthesis of a novel series of thienopyrimidines as highly potent and selective PI3K inhibitors. 5-Amino-2-methoxypyridine is also used to synthesize EMPA (E521550); a novel high-affinity selective antagonist for the OX2 receptor.

Check Digit Verification of cas no

The CAS Registry Mumber 6628-77-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,6,2 and 8 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 6628-77:
(6*6)+(5*6)+(4*2)+(3*8)+(2*7)+(1*7)=119
119 % 10 = 9
So 6628-77-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H8N2O/c1-9-6-3-2-5(7)4-8-6/h2-4H,7H2,1H3

6628-77-9 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (H27528)  5-Amino-2-methoxypyridine, 98%   

  • 6628-77-9

  • 5g

  • 503.0CNY

  • Detail
  • Alfa Aesar

  • (H27528)  5-Amino-2-methoxypyridine, 98%   

  • 6628-77-9

  • 25g

  • 1683.0CNY

  • Detail
  • Aldrich

  • (A61209)  5-Amino-2-methoxypyridine  95%

  • 6628-77-9

  • A61209-5G

  • 482.04CNY

  • Detail
  • Aldrich

  • (A61209)  5-Amino-2-methoxypyridine  95%

  • 6628-77-9

  • A61209-25G

  • 1,843.92CNY

  • Detail

6628-77-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Amino-2-methoxypyridine

1.2 Other means of identification

Product number -
Other names 3-Pyridinamine, 6-methoxy-

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:6628-77-9 SDS

6628-77-9Synthetic route

2-methoxy-5-nitropyridine
5446-92-4

2-methoxy-5-nitropyridine

6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;100%
With cyclohexa-1,4-diene; 5%-palladium/activated carbon In methanol at 120℃; for 0.0833333h; Microwave irradiation;99%
With iron; calcium chloride In ethanol for 2h; Heating;97%
2-methoxy-5-bromopyridine
13472-85-0

2-methoxy-5-bromopyridine

6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere;95%
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; Sealed tube;86%
Multi-step reaction with 2 steps
1.1: copper(l) iodide; potassium carbonate; L-proline / dimethyl sulfoxide / Inert atmosphere
1.2: 80 °C / Inert atmosphere
2.1: palladium on activated charcoal; ammonium formate / methanol / Reflux
View Scheme
2-methoxy-5-nitropyridine N-oxide
96530-77-7

2-methoxy-5-nitropyridine N-oxide

6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
With iron In acetic acid89%
2-chloro-5-nitropyridine
4548-45-2

2-chloro-5-nitropyridine

6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
With sodium hydroxide anschliessendes Hydrieren an Palladium/CaCO3;
Multi-step reaction with 2 steps
2: iron-powder; acetic acid; aqueous methanol
View Scheme
Multi-step reaction with 2 steps
2: platinum; ethanol / Hydrogenation
View Scheme
2-bromo-6-methoxy-3-nitropyridine

2-bromo-6-methoxy-3-nitropyridine

6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
With hydrogen; Lindlar's catalyst In ethanol
6-methyoxy-3-pyridinecarboxamide
7150-23-4

6-methyoxy-3-pyridinecarboxamide

6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
With sodium hydroxide; bromine In tetrahydrofuran at 5 - 70℃; Hoffmann rearrangement;
2-chloro-5-nitropyridine
4548-45-2

2-chloro-5-nitropyridine

potassium-salt of/the/ 4-acetylamino-benzenesulfinic acid

potassium-salt of/the/ 4-acetylamino-benzenesulfinic acid

6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / NaH / tetrahydrofuran / 1 h / Ambient temperature
2: hydrogen / 5 percent Pd/C / methanol / 760 Torr / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 99 percent / 1.) sodium metal / 24 h / 70 °C / Heating
2: cyclohexene / 5percent Pd-C / ethanol / Heating
View Scheme
6-bromo-2-methoxypyridine
40473-07-2

6-bromo-2-methoxypyridine

6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / potassium nitrate, concd. H2SO4 / 2 h / 75 °C
2: H2 / 5percent Pd/CaCO3 / ethanol
View Scheme
2-iodo-5-nitropyridine
28080-54-8

2-iodo-5-nitropyridine

6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium methylate; methanol
2: SnCl2; HCl; diethyl ether
View Scheme
N-benzyl-6-methoxypyridin-3-amine
342793-48-0

N-benzyl-6-methoxypyridin-3-amine

6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
With palladium on activated charcoal; ammonium formate In methanol Reflux;
5-nitro-pyridin-2-ylamine
4214-76-0

5-nitro-pyridin-2-ylamine

6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogenchloride; sodium nitrite / water / 0.67 h / 0 - 6 °C
2: trichlorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C / Reflux
3: methanol / 1 h / Reflux
4: palladium 10% on activated carbon; hydrogen / methanol / 1 h / 60 °C / 7500.75 Torr
View Scheme
Multi-step reaction with 4 steps
1: sodium hydroxide / Reflux
2: trichlorophosphate / N,N-dimethyl-formamide / Reflux
3: Reflux
4: iron; acetic acid / ethanol / Reflux
View Scheme
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

diethyl 2-ethoxymethylenemalonate
87-13-8

diethyl 2-ethoxymethylenemalonate

diethyl {[(6-methoxypyridin-3-yl)amino]methylidene}propanedioate
53241-90-0

diethyl {[(6-methoxypyridin-3-yl)amino]methylidene}propanedioate

Conditions
ConditionsYield
In ethanol for 4h; Heating / reflux;100%
In ethanol for 4h; Heating / reflux;100%
In ethanol for 4h; Heating / reflux;100%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

2-bromo-6-methoxy-pyridin-3-ylamine
135795-46-9

2-bromo-6-methoxy-pyridin-3-ylamine

Conditions
ConditionsYield
With bromine; sodium acetate In acetic acid at 20℃; for 0.5h;100%
With hydrogen bromide; dihydrogen peroxide In water at 5 - 20℃;97%
With bromine; sodium acetate In acetic acid for 0.333333h;60%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

pivaloyl chloride
3282-30-2

pivaloyl chloride

2,2-dimethyl-N-<5-(2-methoxypyridinyl)>propanamide
227180-19-0

2,2-dimethyl-N-<5-(2-methoxypyridinyl)>propanamide

Conditions
ConditionsYield
With triethylamine In dichloromethane for 0.5h; Cooling with ice;100%
With triethylamine In dichloromethane 0 deg C, 10 min; RT, 2h;99%
With triethylamine In dichloromethane at 0 - 20℃; for 2.16667h;
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

6-methoxypyridin-3-diazonium tetrafluoroborate

6-methoxypyridin-3-diazonium tetrafluoroborate

Conditions
ConditionsYield
With tetrafluoroboric acid; sodium nitrite In ethanol; water at 0℃; for 3h;100%
With tetrafluoroboric acid; sodium nitrite In ethanol; water at 0℃; for 3h; Product distribution / selectivity;91%
With tetrafluoroboric acid; sodium nitrite In ethanol; water at 0℃; for 2h;91%
Stage #1: 6-methoxy-pyridin-3-ylamine With boron trifluoride diethyl etherate In tetrahydrofuran for 0.0833333h; Cooling with ice;
Stage #2: With tert.-butylnitrite In tetrahydrofuran at 0℃;
80%
With tetrafluoroboric acid; sodium nitrite at 5℃;72%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

3,3-tetramethylene glutaric anhydride
5662-95-3

3,3-tetramethylene glutaric anhydride

8-(6-methoxypyridin-3-yl)-8-azaspiro[4.5]decane-7,9-dione hydrochloride

8-(6-methoxypyridin-3-yl)-8-azaspiro[4.5]decane-7,9-dione hydrochloride

Conditions
ConditionsYield
Stage #1: 6-methoxy-pyridin-3-ylamine; 3,3-tetramethylene glutaric anhydride In dichloromethane at 20℃; for 3h;
Stage #2: With thionyl chloride In dichloromethane at 20℃; for 3.5h;
100%
Stage #1: 6-methoxy-pyridin-3-ylamine; 3,3-tetramethylene glutaric anhydride In dichloromethane at 20℃; for 3h;
Stage #2: With thionyl chloride In dichloromethane at 20℃; for 3.5h;
100%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

cyclohexanylcarbonyl chloride
2719-27-9

cyclohexanylcarbonyl chloride

cyclohexanecarboxylic acid (6-methoxy-pyridin-3-yl)-amide hydrochloride
548763-48-0

cyclohexanecarboxylic acid (6-methoxy-pyridin-3-yl)-amide hydrochloride

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether100%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

cyclohexylacetic acid chloride
23860-35-7

cyclohexylacetic acid chloride

2-Cyclohexyl-N-(6-methoxy-pyridin-3-yl)-acetamide hydrochloride
548763-51-5

2-Cyclohexyl-N-(6-methoxy-pyridin-3-yl)-acetamide hydrochloride

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether100%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione
15568-85-1

5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

5-[[(6-methoxypyridin-3-yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
25063-69-8

5-[[(6-methoxypyridin-3-yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
In isopropyl alcohol Heating;100%
In isopropyl alcohol at 70℃; for 0.5h;
In isopropyl alcohol for 1h; Heating / reflux;
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

3,4-diethoxy-3-cyclobuten-1,2-dione
5231-87-8

3,4-diethoxy-3-cyclobuten-1,2-dione

C12H12N2O4
1018682-14-8

C12H12N2O4

Conditions
ConditionsYield
In methanol; water for 0.5h; Heating;100%
1,2,3-triazole
288-36-8

1,2,3-triazole

6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

C12H13ClN2O2
864178-16-5

C12H13ClN2O2

A

5-[3-(4-ethoxy-3-methyl-phenyl)-5-[1,2,3]triazol-2-ylmethyl-[1,2,4]triazol-4-yl]-2-methoxy-pyridine

5-[3-(4-ethoxy-3-methyl-phenyl)-5-[1,2,3]triazol-2-ylmethyl-[1,2,4]triazol-4-yl]-2-methoxy-pyridine

B

5-[3-(4-ethoxy-3-methyl-phenyl)-5-[1,2,3]triazol-1-ylmethyl-[1,2,4]triazol-4-yl]-2-methoxy-pyridine

5-[3-(4-ethoxy-3-methyl-phenyl)-5-[1,2,3]triazol-1-ylmethyl-[1,2,4]triazol-4-yl]-2-methoxy-pyridine

Conditions
ConditionsYield
Stage #1: 1,2,3-triazole; C12H13ClN2O2 With potassium carbonate In DMF (N,N-dimethyl-formamide); acetonitrile for 18h;
Stage #2: 6-methoxy-pyridin-3-ylamine; toluene-4-sulfonic acid In xylene at 140℃; for 6h;
A 100%
B 100%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

1,1'-Thiocarbonyldiimidazole
6160-65-2

1,1'-Thiocarbonyldiimidazole

5-isothiocyanato-2-methoxypyridine
52023-93-5

5-isothiocyanato-2-methoxypyridine

Conditions
ConditionsYield
In tetrahydrofuran100%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

3-methoxyphenylacetic acid chloride
6834-42-0

3-methoxyphenylacetic acid chloride

2-(3-methoxyphenyl)-N-{2-methoxy(5-pyridyl)}acetamide
295318-90-0

2-(3-methoxyphenyl)-N-{2-methoxy(5-pyridyl)}acetamide

Conditions
ConditionsYield
99%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

trimethylpyruvic acid
815-17-8

trimethylpyruvic acid

C12H18N2O3
1028253-88-4

C12H18N2O3

Conditions
ConditionsYield
Stage #1: 6-methoxy-pyridin-3-ylamine; trimethylpyruvic acid With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 24h;
Stage #2: With water; ammonium chloride In 1,2-dichloro-ethane
99%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

4-(chlorosulfonyl)benzenesulfonyl fluoride

4-(chlorosulfonyl)benzenesulfonyl fluoride

C12H11FN2O5S2

C12H11FN2O5S2

Conditions
ConditionsYield
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction;99%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

2,4-dichloroquinazoline
607-68-1

2,4-dichloroquinazoline

2-chloro-N-(6-methoxypyridin-3-yl)quinazolin-4-amine

2-chloro-N-(6-methoxypyridin-3-yl)quinazolin-4-amine

Conditions
ConditionsYield
With sodium acetate In tetrahydrofuran; water at 60℃; for 0.75h;98%
With sodium acetate In tetrahydrofuran; water at 60℃; for 0.75h;98%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl N-(6-methoxypyridin-3-yl)carbamate
183741-80-2

tert-butyl N-(6-methoxypyridin-3-yl)carbamate

Conditions
ConditionsYield
In 1,4-dioxane Reflux;97%
In 1,4-dioxane96%
In 1,4-dioxane for 0.5h; Heating;94%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

5-methoxythiazolo[5,4-b]pyridin-2-amine
13797-77-8

5-methoxythiazolo[5,4-b]pyridin-2-amine

Conditions
ConditionsYield
Stage #1: 6-methoxy-pyridin-3-ylamine; ammonium thiocyanate In acetonitrile at 20℃; for 0.166667h;
Stage #2: With benzyltrimethylazanium tribroman-2-uide In acetonitrile at 20℃;
97%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

3-(2-Chloro-4-phenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester
710324-65-5

3-(2-Chloro-4-phenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester

3-[2-(6-Methoxy-pyridin-3-ylamino)-4-phenylamino-pyrimidin-5-yl]-2-(4-methoxy-phenyl)-propionic acid methyl ester
710324-66-6

3-[2-(6-Methoxy-pyridin-3-ylamino)-4-phenylamino-pyrimidin-5-yl]-2-(4-methoxy-phenyl)-propionic acid methyl ester

Conditions
ConditionsYield
In ethyl acetate at 110℃; for 4h;96.8%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

phenyl chloroformate
1885-14-9

phenyl chloroformate

(6-methoxy-pyridin-3-yl)-carbamic acid phenyl ester
102671-59-0

(6-methoxy-pyridin-3-yl)-carbamic acid phenyl ester

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 0 - 20℃; for 12h;96%
With pyridine In tetrahydrofuran at 0 - 20℃;96%
With pyridine In tetrahydrofuran at 0 - 20℃;96%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

methyl 2-chloropyridine-3-carboxylate
40134-18-7

methyl 2-chloropyridine-3-carboxylate

methyl 2-(6-methoxy-3-pyridinyl)aminonicotinate
1239165-03-7

methyl 2-(6-methoxy-3-pyridinyl)aminonicotinate

Conditions
ConditionsYield
With caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 90℃; for 72h;96%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

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

2,2,2-Trichloroethyl chloroformate

2,2,2-trichloroethyl (6-methoxypyridin-3-yl)carbamate
887624-73-9

2,2,2-trichloroethyl (6-methoxypyridin-3-yl)carbamate

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 0℃; for 0.5h;95.4%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

5-[[(6-methoxypyridin-3-yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
25063-69-8

5-[[(6-methoxypyridin-3-yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
In ethanol for 1h; Reflux; Large scale;95%
In ethanol for 1h; Reflux; Large scale;95%
In ethanol for 1h; Reflux; Large scale;95%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

5-hydrazinyl-2-methoxy pyridine
160664-95-9

5-hydrazinyl-2-methoxy pyridine

Conditions
ConditionsYield
Stage #1: 6-methoxy-pyridin-3-ylamine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h;
Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate In water at 0℃; for 2.5h;
Stage #3: With potassium hydroxide In water
95%
Stage #1: 6-methoxy-pyridin-3-ylamine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h;
Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate In water at 0℃; for 2.5h;
95%
Stage #1: 6-methoxy-pyridin-3-ylamine With hydrogenchloride; water; sodium nitrite at 0 - 5℃;
Stage #2: With hydrogenchloride; tin(ll) chloride at -25 - -20℃; for 2.5h;
Stage #3: With water; potassium hydroxide In dichloromethane at 0 - 5℃; for 1.5h;
70%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

2-(4-(2-bromobenzoyl)phenoxy)acetic acid

2-(4-(2-bromobenzoyl)phenoxy)acetic acid

2-[4-(2-bromobenzoyl)phenoxy]-N-(6-methoxypyridin-3-yl)acetamide

2-[4-(2-bromobenzoyl)phenoxy]-N-(6-methoxypyridin-3-yl)acetamide

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;94%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

2-[(5-fluoropyridine-2-carbonyl)amino]malonic acid diethyl ester
787564-31-2

2-[(5-fluoropyridine-2-carbonyl)amino]malonic acid diethyl ester

5-(5-fluoro-2-pyridyl)-1-(6-methoxy-3-pyridyl)-1H-1,2,4-triazole-3-carboxylic acid sodium salt
787564-29-8

5-(5-fluoro-2-pyridyl)-1-(6-methoxy-3-pyridyl)-1H-1,2,4-triazole-3-carboxylic acid sodium salt

Conditions
ConditionsYield
Stage #1: 6-methoxy-pyridin-3-ylamine With hydrogenchloride; acetic acid; sodium nitrite In water at 0℃; for 0.25h;
Stage #2: 2-[(5-fluoropyridine-2-carbonyl)amino]malonic acid diethyl ester With potassium carbonate In water; acetone at -15 - 0℃; for 2.5h;
Stage #3: With sodium methylate In methanol at 20℃; for 60h;
93%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

tert-butyl 6-oxo-3-azabicyclo[3.1.1]heptane-3-carboxylate

tert-butyl 6-oxo-3-azabicyclo[3.1.1]heptane-3-carboxylate

tert-butyl 6-((6-methoxypyridin-3-yl)amino)-3-azabicyclo[3.1.1]heptane-3-carboxylate

tert-butyl 6-((6-methoxypyridin-3-yl)amino)-3-azabicyclo[3.1.1]heptane-3-carboxylate

Conditions
ConditionsYield
With nido-decaborane In methanol; trans-1,2-dichloroethylene at 20℃; Inert atmosphere;93%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

1,1'-Thiocarbonyldi-2(1H)-pyridone
102368-13-8

1,1'-Thiocarbonyldi-2(1H)-pyridone

5-isothiocyanato-2-methoxypyridine
52023-93-5

5-isothiocyanato-2-methoxypyridine

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 3.5h;92%
6-methoxy-pyridin-3-ylamine
6628-77-9

6-methoxy-pyridin-3-ylamine

4-fluorophthalic anhydride
319-03-9

4-fluorophthalic anhydride

5-fluoro-2-(6-methoxypyridin-3-yl)isoindoline-1,3-dione

5-fluoro-2-(6-methoxypyridin-3-yl)isoindoline-1,3-dione

Conditions
ConditionsYield
With sodium acetate; acetic acid at 118℃; for 2h;91.4%

6628-77-9Relevant articles and documents

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction

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Paragraph 0111-0118; 0121, (2021/05/29)

The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.

Methnaridine is an orally bioavailable, fast-killing and long-acting antimalarial agent that cures Plasmodium infections in mice

Wang, Weisi,Yao, Junmin,Chen, Zhuo,Sun, Yiming,Shi, Yuqing,Wei, Yufen,Zhou, Hejun,Yu, Yingfang,Li, Shizhu,Duan, Liping

, p. 5569 - 5579 (2020/11/03)

Background and Purpose: Malaria is one of the deadliest diseases in the world. Novel chemotherapeutic agents are urgently required to combat the widespread Plasmodium resistance to frontline drugs. Here, we report the discovery of a novel benzonaphthyridine antimalarial, methnaridine, which was identified using a structural optimization strategy. Experimental Approach: An integrated pharmacological approach was used to evaluate the antimalarial profile of methnaridine. The pharmacokinetic properties of methnaridine were investigated along with the associated safety profile. Host immune response patterns were also analysed. Key Results: Methnaridine exhibited potent antimalarial activity against P. falciparum (3D7: IC50 = 0.0066 μM; Dd2: IC50 = 0.0056 μM). In P. berghei-infected mice, oral administration effectively suppressed parasitemia (ED50 = 0.52 mg·kg?1·day?1) and cured the established infection (CD50 = 10.13 mg·kg?1·day?1). These results are equivalent to or better than those of other antimalarial agents in clinical use. Notably, a four-dose oral regimen at a dosage of 25 mg·kg?1 achieved a complete cure of P. berghei infection in mice. Methnaridine exhibited a rapid parasiticidal profile (PCT99 = 36.0 h) and showed no cross-resistance to chloroquine. Pharmacokinetic studies revealed that methnaridine is readily absorbed, long-lasting and slowly cleared. The safety profile of methnaridine is also satisfactory (maximum tolerated dose = 1,125 mg·kg?1). In addition, following methnaridine treatment, infection-induced Th1 immune response was almost fully alleviated in mice. Conclusion and Implications: Methnaridine is an orally bioavailable, fast-acting and long-lasting agent with excellent antimalarial properties. Our study highlights the potential of methnaridine for clinical development as a promising antimalarial candidate.

Preparation method for malaridine intermediate 2-methoxy-5-aminopyridine

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, (2016/10/10)

The invention provides a green environment-friendly preparation method for a malaridine intermediate 2-methoxy-5-aminopyridine. The preparation method comprises the specific method: with 2-aminopyridine as a raw material, nitrating 2-aminopyridine with a mixed acid in the presence of a solvent to obtain 2-amino-5-nitropyridine; and carrying out hydrolysis, chlorination, methoxylation and reduction to obtain the intermediate 2-methoxy-5-aminopyridine. The preparation method has the advantages of simple process, short production cycle, mild reaction conditions, fewer three wastes, high product purity and yield, cheap and easily obtained raw materials, and higher economic property and environmental protection, and is suitable for industrialized production.

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