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14667-47-1

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14667-47-1 Usage

Chemical Properties

Off white powder

Uses

Methyl 2-Aminonicotinate is used to prepare 2-{4-[(3S)-Piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (MK-4827)as a novel oral poly(ADP-ribose)polymerase (PARP) inhibitor efficacious in BRCA-1 and -2 mutant tumors. It is also used to synthesize quinazolinone/quinazoline thione derivatives as phosphodiesterase 7 inhibitors.

Check Digit Verification of cas no

The CAS Registry Mumber 14667-47-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,6,6 and 7 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 14667-47:
(7*1)+(6*4)+(5*6)+(4*6)+(3*7)+(2*4)+(1*7)=121
121 % 10 = 1
So 14667-47-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H8N2O2/c1-11-7(10)5-3-2-4-9-6(5)8/h2-4H,1H3,(H2,8,9)

14667-47-1 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (H50013)  Methyl 2-aminonicotinate, 97%   

  • 14667-47-1

  • 1g

  • 1525.0CNY

  • Detail
  • Alfa Aesar

  • (H50013)  Methyl 2-aminonicotinate, 97%   

  • 14667-47-1

  • 5g

  • 6853.0CNY

  • Detail
  • Aldrich

  • (715107)  Methyl2-aminopyridine-3-carboxylate  97%

  • 14667-47-1

  • 715107-1G

  • 352.17CNY

  • Detail
  • Aldrich

  • (715107)  Methyl2-aminopyridine-3-carboxylate  97%

  • 14667-47-1

  • 715107-5G

  • 1,048.32CNY

  • Detail
  • Aldrich

  • (715107)  Methyl2-aminopyridine-3-carboxylate  97%

  • 14667-47-1

  • 715107-1G

  • 352.17CNY

  • Detail
  • Aldrich

  • (715107)  Methyl2-aminopyridine-3-carboxylate  97%

  • 14667-47-1

  • 715107-5G

  • 1,048.32CNY

  • Detail
  • Aldrich

  • (715107)  Methyl2-aminopyridine-3-carboxylate  97%

  • 14667-47-1

  • 715107-1G

  • 352.17CNY

  • Detail
  • Aldrich

  • (715107)  Methyl2-aminopyridine-3-carboxylate  97%

  • 14667-47-1

  • 715107-5G

  • 1,048.32CNY

  • Detail
  • Aldrich

  • (715107)  Methyl2-aminopyridine-3-carboxylate  97%

  • 14667-47-1

  • 715107-1G

  • 352.17CNY

  • Detail
  • Aldrich

  • (715107)  Methyl2-aminopyridine-3-carboxylate  97%

  • 14667-47-1

  • 715107-5G

  • 1,048.32CNY

  • Detail

14667-47-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl 2-aminopyridine-3-carboxylate

1.2 Other means of identification

Product number -
Other names methyl 2-aminopyridine-3-carboxylate

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:14667-47-1 SDS

14667-47-1Synthetic route

2-aminopyridin-3-carboxylic acid
5345-47-1

2-aminopyridin-3-carboxylic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

Conditions
ConditionsYield
In methanol; toluene at 0℃; for 0.5h;95%
In methanol; diethyl ether; toluene at 0℃; for 0.75h; Inert atmosphere;90%
In methanol; hexane for 0.5h;
2-aminopyridin-3-carboxylic acid
5345-47-1

2-aminopyridin-3-carboxylic acid

2-chloro-1,3-dimethyl imidazolium chloride

2-chloro-1,3-dimethyl imidazolium chloride

methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 1h;94%
methanol
67-56-1

methanol

2-aminopyridin-3-carboxylic acid
5345-47-1

2-aminopyridin-3-carboxylic acid

methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

Conditions
ConditionsYield
With sulfuric acid at 0 - 60℃; under 760.051 Torr; for 1.5h; Inert atmosphere; Microwave irradiation;93%
With thionyl chloride at 0 - 80℃; for 3h;86%
With sulfuric acid at 80℃; for 7h;63%
2-aminopyridin-3-carboxylic acid
5345-47-1

2-aminopyridin-3-carboxylic acid

2-chloro-1,3-dimethylimidazolinium chloride
37091-73-9

2-chloro-1,3-dimethylimidazolinium chloride

methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

Conditions
ConditionsYield
With triethylamine In methanol for 1h; Ambient temperature;84%
2-aminopyridin-3-carboxylic acid
5345-47-1

2-aminopyridin-3-carboxylic acid

methyl iodide
74-88-4

methyl iodide

methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 18h; Reflux;71%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Reflux;58%
Stage #1: 2-aminopyridin-3-carboxylic acid With potassium carbonate In N,N-dimethyl-formamide Reflux;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 18h; Reflux;
58%
With potassium carbonate In N,N-dimethyl-formamide for 18h;3.2 g
2-aminopyridin-3-carboxylic acid
5345-47-1

2-aminopyridin-3-carboxylic acid

methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

Conditions
ConditionsYield
In methanol; diethyl ether at 0℃;
3-amino-pyridine-2-carboxylic acid
1462-86-8

3-amino-pyridine-2-carboxylic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

Conditions
ConditionsYield
With methanol In diethyl ether; toluene at 20℃; Inert atmosphere;
C11H14N2O3

C11H14N2O3

methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

Conditions
ConditionsYield
With dodecacarbonyl-triangulo-triruthenium; 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane; isopropyl alcohol at 140℃; for 24h; Inert atmosphere; Sealed tube;70 %Spectr.
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

2-amino-5-bromonicotinic acid ethyl ester
433226-06-3

2-amino-5-bromonicotinic acid ethyl ester

Conditions
ConditionsYield
With bromine; sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 1h;99%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

methyl 2-amino-5-bromopyridine-3-carboxylate
50735-34-7

methyl 2-amino-5-bromopyridine-3-carboxylate

Conditions
ConditionsYield
With bromine; sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 1h;99%
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 2h;77%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

triphenylphosphine
603-35-0

triphenylphosphine

N-(3-methoxycarbonyl-2-pyridyl)triphenyliminophosphorane
199733-96-5

N-(3-methoxycarbonyl-2-pyridyl)triphenyliminophosphorane

Conditions
ConditionsYield
With hexachloroethane; triethylamine In benzene for 3.5h; Heating;98%
With diethylazodicarboxylate In dichloromethane; toluene at 20℃; for 2.16667h; Mitsunobu type reaction;87%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

2-aminonicotinic acid hydrazide
5327-31-1

2-aminonicotinic acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 90℃; for 15h; Inert atmosphere;96%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

O-(4-methoxybenzyl)hydroxylamine
21038-22-2

O-(4-methoxybenzyl)hydroxylamine

C14H15N3O3
1268706-67-7

C14H15N3O3

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 2h;95%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

methyl 2-amino-5-chloro-3-pyridinecarboxylate
50735-33-6

methyl 2-amino-5-chloro-3-pyridinecarboxylate

Conditions
ConditionsYield
With N-chloro-succinimide In acetonitrile at 60℃; for 6h; Concentration; Temperature; Solvent;93%
With hydrogenchloride; tert-butylhypochlorite In methanol26%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

2-aminonicotinic acid methyl ester N-oxide
1391062-92-2

2-aminonicotinic acid methyl ester N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol; water at 20℃;88%
With dihydrogen peroxide In ethanol; water at 20℃; for 3h;78%
Stage #1: methyl 2-aminonicotinate With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol at 20℃; for 3h;
Stage #2: manganese(IV) oxide In ethanol
63%
With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol; water at 20℃; for 3h;63%
phosgene
75-44-5

phosgene

methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

6-amino-7-fluoro-4-(4-methoxybenzyl)-2H-benzo[b][1,4]oxazine-3(4H)-one

6-amino-7-fluoro-4-(4-methoxybenzyl)-2H-benzo[b][1,4]oxazine-3(4H)-one

methyl 2-(3-(7-fluoro-4-(4-methoxybenzyl)3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-yl)ureido)nicotinate

methyl 2-(3-(7-fluoro-4-(4-methoxybenzyl)3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-yl)ureido)nicotinate

Conditions
ConditionsYield
Stage #1: phosgene; 6-amino-7-fluoro-4-(4-methoxybenzyl)-2H-benzo[b][1,4]oxazine-3(4H)-one In 1,4-dioxane at 0℃; for 10.5h; Reflux;
Stage #2: methyl 2-aminonicotinate In 1,4-dioxane for 6h; Inert atmosphere; Reflux;
87%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-(2-aminopyridin-3-yl)propan-2-ol
213666-96-7

2-(2-aminopyridin-3-yl)propan-2-ol

Conditions
ConditionsYield
In tetrahydrofuran at -20 - 20℃; for 2.5h; Inert atmosphere;86%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

1-bromoacetone
598-31-2

1-bromoacetone

methyl 2-methyl-imidazo[1,2-α]pyridine-8-carboxylate
133427-09-5

methyl 2-methyl-imidazo[1,2-α]pyridine-8-carboxylate

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol85%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

2-ethoxybenzoyl chloride
42926-52-3

2-ethoxybenzoyl chloride

methyl 2-(2-ethoxybenzamido)nicotinate

methyl 2-(2-ethoxybenzamido)nicotinate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 4h;85%
With triethylamine In dichloromethane at 0 - 20℃;
phosgene
75-44-5

phosgene

methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

6-amino-2,2,7-trifluoro-4-(4-methoxybenzyl)-2H-benzo[b][1,4]oxazine-3(4H)-one

6-amino-2,2,7-trifluoro-4-(4-methoxybenzyl)-2H-benzo[b][1,4]oxazine-3(4H)-one

methyl 2-(3-(2,2,7-trifluoro-4-(4-methoxybenzyl)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)ureido)nicotinate

methyl 2-(3-(2,2,7-trifluoro-4-(4-methoxybenzyl)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)ureido)nicotinate

Conditions
ConditionsYield
Stage #1: phosgene; 6-amino-2,2,7-trifluoro-4-(4-methoxybenzyl)-2H-benzo[b][1,4]oxazine-3(4H)-one In 1,4-dioxane at 0℃; for 10.5h; Reflux;
Stage #2: methyl 2-aminonicotinate In 1,4-dioxane for 6h; Inert atmosphere; Reflux;
85%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

methyl 2-((4-methylphenyl)sulfonamido)nicotinate

methyl 2-((4-methylphenyl)sulfonamido)nicotinate

Conditions
ConditionsYield
With pyridine at 20℃; for 24h;84%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

2-amino-3-(methoxycarbonyl)-5-nitropyridine
88312-64-5

2-amino-3-(methoxycarbonyl)-5-nitropyridine

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 0 - 20℃; for 2h; Inert atmosphere; regioselective reaction;82%
With sulfuric acid; nitric acid at 0 - 70℃; for 23.75h;68%
Stage #1: methyl 2-aminonicotinate With sulfuric acid; nitric acid; sodium hydrogencarbonate at 0 - 70℃; for 23.66h;
Stage #2: With sodium hydrogencarbonate In water at 0℃;
35%
Stage #1: methyl 2-aminonicotinate With sulfuric acid; nitric acid at 0 - 70℃; for 23.6667h;
Stage #2: With sodium hydrogencarbonate In water at 0℃;
35%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

m-anisoyl chloride
1711-05-3

m-anisoyl chloride

methyl 2-(3-methoxybenzamido)nicotinate

methyl 2-(3-methoxybenzamido)nicotinate

Conditions
ConditionsYield
With triethylamine at 0 - 20℃; for 12h;79%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

Ethyl hexanoate
123-66-0

Ethyl hexanoate

3-Butyl-4-hydroxy-1H-[1,8]naphthyridin-2-one
115891-79-7

3-Butyl-4-hydroxy-1H-[1,8]naphthyridin-2-one

Conditions
ConditionsYield
With potassium tert-butylate 1.) 0.25 h, 2.) heating, 4 h;76%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

methyl 2-[bis(tert-butoxycarbonyl)amino]nicotinate
877593-10-7

methyl 2-[bis(tert-butoxycarbonyl)amino]nicotinate

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 36h;75%
With dmap In dichloromethane for 48h; Inert atmosphere;
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

methyl 2-iodonicotinate
913836-18-7

methyl 2-iodonicotinate

C14H13N3O4

C14H13N3O4

Conditions
ConditionsYield
With copper; potassium carbonate In 1,2-dichloro-benzene at 180℃; for 48h; Inert atmosphere;73.2%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

thiophosgene
463-71-8

thiophosgene

methyl 2-isothiocyanatonicotinate
1360964-43-7

methyl 2-isothiocyanatonicotinate

Conditions
ConditionsYield
In dichloromethane at 0℃; for 2h;70.51%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

benzoyl chloride
98-88-4

benzoyl chloride

methyl 2-(N-benzoylamino)-nicotinate
144267-78-7

methyl 2-(N-benzoylamino)-nicotinate

Conditions
ConditionsYield
With triethylamine at 0 - 20℃; for 12h;69%
With pyridine Yield given;
3-pyridinecarbonyl chloride
10400-19-8

3-pyridinecarbonyl chloride

methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

methyl 2-(nicotinamido)nicotinate

methyl 2-(nicotinamido)nicotinate

Conditions
ConditionsYield
With triethylamine at 0 - 20℃; for 12h;68%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

phenoxyacetic acid ethyl ester
2555-49-9

phenoxyacetic acid ethyl ester

C14H10N2O3
1367847-18-4

C14H10N2O3

Conditions
ConditionsYield
With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;67%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

acetic anhydride
108-24-7

acetic anhydride

2-Methyl-4H-pyrido<2,3-d><3,1>oxazin-4-one
3809-93-6

2-Methyl-4H-pyrido<2,3-d><3,1>oxazin-4-one

Conditions
ConditionsYield
at 20℃;65%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

1,3-dioxoisoindolin-2-yl 3,3-dimethylbutanoate
84379-72-6

1,3-dioxoisoindolin-2-yl 3,3-dimethylbutanoate

methyl 2-amino-6-(tert-butyl)nicotinate

methyl 2-amino-6-(tert-butyl)nicotinate

Conditions
ConditionsYield
With diphenyl hydrogen phosphate In 1,4-dioxane at 20℃; for 15h; Minisci Aromatic Substitution; Sealed tube; Irradiation; Glovebox; Inert atmosphere; Green chemistry;65%
methyl 2-aminonicotinate
14667-47-1

methyl 2-aminonicotinate

(2-iodo-phenyl)-methanesulfonyl chloride
25068-94-4

(2-iodo-phenyl)-methanesulfonyl chloride

methyl 2-{[(2-iodobenzyl)sulfonyl]amino}nicotinate
1362699-05-5

methyl 2-{[(2-iodobenzyl)sulfonyl]amino}nicotinate

Conditions
ConditionsYield
Stage #1: methyl 2-aminonicotinate; (2-iodo-phenyl)-methanesulfonyl chloride With pyridine In dichloromethane at 20℃; for 12h;
Stage #2: With hydrogenchloride In dichloromethane; water
63%

14667-47-1Relevant articles and documents

Rational multistep synthesis of a novel polyfunctionalized benzo[d]thiazole and its thiazolo[5,4-b]pyridine analogue

Hédou, Damien,Deau, Emmanuel,Harari, Marine,Sanselme, Morgane,Fruit, Corinne,Besson, Thierry

, p. 5541 - 5549 (2014)

Reliable synthetic routes were studied for an access to a novel polyfunctionalized 6-amino-2-cyanobenzo[d]thiazole-5-carboxylate ester (1) and its analogue 5-amino-2-cyanothiazolo[5,4-b]pyridine-6-carboxylate ester (2). Both compounds 1 and 2 are functionalized as molecular bricks for the synthesis of innovative molecular systems. Part of the chemistry performed in this study was achieved under microwave irradiation.

Preparation and chemical behavior of 2-(tert-butoxycarbonyl)amino-3- bromomethyl pyridine, a novel alkylating agent

Krasavin, Mikhail,Shkavrov, Sergey,Kravchenko, Dmitry

, p. 181 - 186 (2006)

Synthesis of a novel heterocyclic alkylating agent has been developed. Its instability toward elevated temperatures and/or polar media can be used to prepare 8-aza-1,4-dihydrobenzo[1,3-d]oxazin-2-one. Copyright Taylor & Francis LLC.

Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters

Ronson, Thomas O.,Renders, Evelien,Van Steijvoort, Ben F.,Wang, Xubin,Wybon, Clarence C. D.,Prokopcová, Hana,Meerpoel, Lieven,Maes, Bert U. W.

supporting information, p. 482 - 487 (2019/01/04)

A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.

Discovering a new class of antifungal agents that selectively inhibits microbial carbonic anhydrases

Annunziato, Giannamaria,Giovati, Laura,Angeli, Andrea,Pavone, Marialaura,Del Prete, Sonia,Pieroni, Marco,Capasso, Clemente,Bruno, Agostino,Conti, Stefania,Magliani, Walter,Supuran, Claudiu T.,Costantino, Gabriele

, p. 1537 - 1544 (2018/10/15)

Infections caused by pathogens resistant to the available antimicrobial treatments represent nowadays a threat to global public health. Recently, it has been demonstrated that carbonic anhydrases (CAs) are essential for the growth of many pathogens and their inhibition leads to growth defects. Principal drawbacks in using CA inhibitors (CAIs) as antimicrobial agents are the side effects due to the lack of selectivity toward human CA isoforms. Herein we report a new class of CAIs, which preferentially interacts with microbial CA active sites over the human ones. The mechanism of action of these inhibitors was investigated against an important fungal pathogen, Cryptococcus neoformans, revealing that they are also able to inhibit CA in microbial cells growing in vitro. At our best knowledge, this is the first report on newly designed synthetic compounds selectively targeting β-CAs and provides a proof of concept of microbial CAs suitability as an antimicrobial drug target.

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