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32955-21-8

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32955-21-8 Usage

Chemical Properties

White to yellow or light brown crystal or powder

Uses

2-Amino-5-thiazolecarboxylic Acid Ethyl Ester is used in the synthesis of dual-action antidiabetic agents that inhibit glycogen phosphorylase.

Synthesis Reference(s)

Tetrahedron Letters, 42, p. 2101, 2001 DOI: 10.1016/S0040-4039(01)00161-7

Check Digit Verification of cas no

The CAS Registry Mumber 32955-21-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,2,9,5 and 5 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 32955-21:
(7*3)+(6*2)+(5*9)+(4*5)+(3*5)+(2*2)+(1*1)=118
118 % 10 = 8
So 32955-21-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H8N2O2S/c1-2-10-5(9)4-3-8-6(7)11-4/h3H,2H2,1H3,(H2,7,8)

32955-21-8 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (H31769)  Ethyl 2-aminothiazole-5-carboxylate, 97%   

  • 32955-21-8

  • 1g

  • 760.0CNY

  • Detail
  • Alfa Aesar

  • (H31769)  Ethyl 2-aminothiazole-5-carboxylate, 97%   

  • 32955-21-8

  • 5g

  • 2499.0CNY

  • Detail
  • Aldrich

  • (708437)  Ethyl2-aminothiazole-5-carboxylate  97%

  • 32955-21-8

  • 708437-1G

  • 723.06CNY

  • Detail
  • Aldrich

  • (708437)  Ethyl2-aminothiazole-5-carboxylate  97%

  • 32955-21-8

  • 708437-5G

  • 2,375.10CNY

  • Detail

32955-21-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl 2-amino-1,3-thiazole-5-carboxylate

1.2 Other means of identification

Product number -
Other names 2-aminothiazole-5-carboxylic acid ethyl ester

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:32955-21-8 SDS

32955-21-8Synthetic route

ethyl 3-ethoxyacrylate
1001-26-9

ethyl 3-ethoxyacrylate

urea
57-13-6

urea

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With potassium sulfide; copper In tetrahydrofuran; water at 55℃; for 1.5h; Temperature; Inert atmosphere;95.7%
ethyl 3-ethoxyacrylate
1001-26-9

ethyl 3-ethoxyacrylate

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: ethyl 3-ethoxyacrylate With N-Bromosuccinimide In 1,4-dioxane; water
Stage #2: With thiourea
91%
With ammonium hydroxide; N-Bromosuccinimide; thiourea In 1,4-dioxane; water
thiourea
17356-08-0

thiourea

2-bromo-3-ethoxy-3-hydroxy-propionic acid ethyl ester

2-bromo-3-ethoxy-3-hydroxy-propionic acid ethyl ester

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
In 1,4-dioxane; water at 80℃; for 1h;90%
In 1,4-dioxane; water at 80℃; for 1h;
In 1,4-dioxane at 80℃; for 1h;1.4 g
ethyl 3-ethoxyacrylate
1001-26-9

ethyl 3-ethoxyacrylate

thiourea
17356-08-0

thiourea

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: ethyl 3-ethoxyacrylate With N-Bromosuccinimide In 1,4-dioxane; water at -10 - 20℃; for 1h;
Stage #2: thiourea In 1,4-dioxane; water at 80℃; for 1h;
70%
Stage #1: ethyl 3-ethoxyacrylate With N-Bromosuccinimide In 1,4-dioxane; water at -10 - 20℃; for 1h;
Stage #2: thiourea In 1,4-dioxane; water at 80℃; for 1h;
Stage #3: With ammonium chloride In 1,4-dioxane; water at 20℃; for 0.166667h;
66%
ethyl 2-chloro-3-oxopropanoate
33142-21-1

ethyl 2-chloro-3-oxopropanoate

thiourea
17356-08-0

thiourea

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
In water 1.) reflux, 15 min, 2.) RT, 12 h;67%
ethyl 2-<2-amino-5-(ethoxycarbonyl)-4-thiazolylthio>acetoacetate
111603-56-6

ethyl 2-<2-amino-5-(ethoxycarbonyl)-4-thiazolylthio>acetoacetate

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With nickel In ethanol for 16h; Heating;39%
2-acetylamino-thiazole-5-carbonitrile
99903-61-4

2-acetylamino-thiazole-5-carbonitrile

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride at 135℃;
ethyl 3-ethoxyacrylate
5941-55-9

ethyl 3-ethoxyacrylate

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-bromosuccinimide / H2O; dioxane / 0.5 h / -10 - 20 °C
2: 90 percent / H2O; dioxane / 1 h / 80 °C
View Scheme
chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

thiourea
17356-08-0

thiourea

formic acid ethyl ester
109-94-4

formic acid ethyl ester

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: chloroacetic acid ethyl ester; formic acid ethyl ester With sodium In ethanol at -10 - -5℃;
Stage #2: thiourea In ethanol at 80℃; for 1.25h;
ethyl 3,3-diethoxypropanoate
10601-80-6

ethyl 3,3-diethoxypropanoate

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2 h / 190 - 200 °C
2: water; N-Bromosuccinimide / 1,4-dioxane / 1 h / -10 - 20 °C
3: 1,4-dioxane / 1 h / 80 °C
View Scheme
ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylate
302964-01-8

ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylate

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
at 225℃; under 38787.1 Torr; for 0.166667h; Flow reactor;
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylate
302964-01-8

ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylate

Conditions
ConditionsYield
dmap In tetrahydrofuran at 30℃; for 5.5h;99.23%
With dmap In tetrahydrofuran at 30℃; for 5.5h;99.23%
In isopropyl alcohol at 50℃; for 24h;93%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

acetic anhydride
108-24-7

acetic anhydride

ethyl 2-acetamidothiazole-5-carboxylate
106840-37-3

ethyl 2-acetamidothiazole-5-carboxylate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0℃; for 2h; Reflux;98%
With pyridine; dmap In dichloromethane for 2h; Reflux;98%
With pyridine; dmap In dichloromethane at 0℃; for 2h; Reflux;98%
3-cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acid
300354-95-4

3-cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acid

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate
56602-33-6

(benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate

2-[3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-propionylamino]-thiazole-5-carboxylic acid ethyl ester
588940-26-5

2-[3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-propionylamino]-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane98%
2,4-dichloro-2-methylpyrimidine
1780-26-3

2,4-dichloro-2-methylpyrimidine

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

ethyl 2-[(6-chloro-2-methylpyrimidin-4-yl)amino]-1,3-thiazole-5-carboxylate
1202357-66-1

ethyl 2-[(6-chloro-2-methylpyrimidin-4-yl)amino]-1,3-thiazole-5-carboxylate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 72h; Inert atmosphere;98%
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 3h; Inert atmosphere;87%
With caesium carbonate In N,N-dimethyl-formamide at 25℃; for 24h; Cooling with ice;83.5%
With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 8.08333h;82%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 3h;81%
cupric chloride

cupric chloride

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

ethyl 2-chloro-thiazole-5-carboxylate
81449-93-6

ethyl 2-chloro-thiazole-5-carboxylate

Conditions
ConditionsYield
With hydrogenchloride; tert.-butylnitrite In acetonitrile97%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

benzoyl chloride
98-88-4

benzoyl chloride

2-Benzoylamino-thiazole-5-carboxylic acid ethyl ester
196937-70-9

2-Benzoylamino-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With pyridine for 48h; Ambient temperature;95%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

p-tert-butyl benzoyl chloride
1710-98-1

p-tert-butyl benzoyl chloride

2-[N-[4-(1,1-Dimethylethyl)benzoyl]amino]thiazole-5-carboxylic Acid Ethyl Ester
439578-91-3

2-[N-[4-(1,1-Dimethylethyl)benzoyl]amino]thiazole-5-carboxylic Acid Ethyl Ester

Conditions
ConditionsYield
With pyridine In dichloromethane88%
2,5-dichloro-N-[2-[(1-methylethyl)sulfonyl]phenyl]-4-pyrimidinamine
761440-16-8

2,5-dichloro-N-[2-[(1-methylethyl)sulfonyl]phenyl]-4-pyrimidinamine

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

C19H20ClN5O4S2

C19H20ClN5O4S2

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; Microwave irradiation;87%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

2-aminothiazole-5-carboxylic acid
40283-46-3

2-aminothiazole-5-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water Reflux;86%
With sodium hydroxide
With barium dihydroxide
With potassium hydroxide In methanol
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

ethyl 2-iodothiazole-5-carboxylate
83553-48-4

ethyl 2-iodothiazole-5-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid; potassium iodide; sodium nitrite In water; acetonitrile at 0 - 20℃;85%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

o-carboxybenzaldehyde
119-67-5

o-carboxybenzaldehyde

3-[(5-thiazolylcarboxyl-2-yl)amino]-2-benzofuran-1(3H)-one

3-[(5-thiazolylcarboxyl-2-yl)amino]-2-benzofuran-1(3H)-one

Conditions
ConditionsYield
In methanol at 20℃; for 1h; Green chemistry;82%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylate
302964-01-8

ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylate

Conditions
ConditionsYield
79.5%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

Ethyl-2-tert-butoxycarbonyloxyamino-thiazole-5-carboxylate

Ethyl-2-tert-butoxycarbonyloxyamino-thiazole-5-carboxylate

Conditions
ConditionsYield
79.5%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

(3-bromo-2-oxopropyl)((tert-butyldiphenylsilyl)imino)(phenyl)-λ6-sulfanone

(3-bromo-2-oxopropyl)((tert-butyldiphenylsilyl)imino)(phenyl)-λ6-sulfanone

ethyl 6-((N-(tert-butyldiphenylsilyl)phenylsulfonimidoyl)methyl)imidazo[2,1-b]thiazole-2-carboxylate

ethyl 6-((N-(tert-butyldiphenylsilyl)phenylsulfonimidoyl)methyl)imidazo[2,1-b]thiazole-2-carboxylate

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane at 90℃; for 15h; Sealed tube; Inert atmosphere;79%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol
127116-19-2

2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol

ethyl (6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formate
1245157-39-4

ethyl (6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-formate

Conditions
ConditionsYield
Stage #1: 2-amino-thiazole-5-carboxylic acid ethyl ester; 2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol With caesium carbonate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 16h; Reflux;
Stage #2: With hydrogenchloride In water; toluene for 0.166667h;
Stage #3: With sodium hydroxide In water at 10 - 15℃; for 1h;
70.5%
N'-[2-cyano-4-methoxy-5-(3-morpholin-4-ylpropoxy)phenyl]-N,N-dimethylimidoformamido

N'-[2-cyano-4-methoxy-5-(3-morpholin-4-ylpropoxy)phenyl]-N,N-dimethylimidoformamido

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

ethyl 2-{[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-yl]amino}-1,3-thiazole-5-carboxylate
385780-23-4

ethyl 2-{[6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-yl]amino}-1,3-thiazole-5-carboxylate

Conditions
ConditionsYield
With acetic acid Heating;70%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

di-(tert-butyl) dicarbonate

di-(tert-butyl) dicarbonate

ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylate
302964-01-8

ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylate

Conditions
ConditionsYield
With dmap; triethanolamine In tetrahydrofuran68%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

A

C16H24N2O6S
1215121-72-4

C16H24N2O6S

B

ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylate
302964-01-8

ethyl 2-[(tert-butoxycarbonyl)amino]-1,3-thiazole-5-carboxylate

Conditions
ConditionsYield
With dmap In dichloromethane for 15h;A 17%
B 65%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

ethyl 2-(tetrahydro-2H-pyran-2-ylamino)thiazole-5-carboxylate
1029088-17-2

ethyl 2-(tetrahydro-2H-pyran-2-ylamino)thiazole-5-carboxylate

Conditions
ConditionsYield
trifluoroacetic acid In acetonitrile Heating / reflux;64%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

6-(3-ethylureido)nicotinic acid
1251126-74-5

6-(3-ethylureido)nicotinic acid

C15H17N5O4S
1644457-07-7

C15H17N5O4S

Conditions
ConditionsYield
Stage #1: 6-(3-ethylureido)nicotinic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: 2-amino-thiazole-5-carboxylic acid ethyl ester In N,N-dimethyl-formamide at 45℃; for 18h;
63%
2-[(3R,5S)-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetic acid
383661-55-0

2-[(3R,5S)-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetic acid

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

(3R,5S)-N-propanesulfonyl-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetamide
383653-04-1

(3R,5S)-N-propanesulfonyl-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetamide

isobutyl chloroformate
543-27-1

isobutyl chloroformate

ethyl 5-[[[(3R,5S)-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]amino]-1,3-thiazole-5-carboxylate

ethyl 5-[[[(3R,5S)-1-(3-acetoxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]amino]-1,3-thiazole-5-carboxylate

Conditions
ConditionsYield
With pyridine; triethylamine In water; N,N-dimethyl-formamide62.1%
3-cyclopentyl-2-(3,4-dichlorophenyl)propionic acid
300355-34-4

3-cyclopentyl-2-(3,4-dichlorophenyl)propionic acid

2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

2-[3-cyclopentyl-2-(3,4-dichlorophenyl)-propionylamino]-thiazole-5-carboxylic acid ethyl ester

2-[3-cyclopentyl-2-(3,4-dichlorophenyl)-propionylamino]-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 25℃; for 14h; Inert atmosphere;61%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

2-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazole-4-carboxylic acid
368869-97-0

2-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazole-4-carboxylic acid

ethyl 2-[2-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazole-4-amido]-1,3-thiazole-5-carboxylate

ethyl 2-[2-(2,3-dihydro-1-benzofuran-5-yl)-1,3-thiazole-4-amido]-1,3-thiazole-5-carboxylate

Conditions
ConditionsYield
With pyridine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate at 90℃; for 3h;53%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

ethyl 2-bromo-1,3-thiazole-5-carboxylate
41731-83-3

ethyl 2-bromo-1,3-thiazole-5-carboxylate

Conditions
ConditionsYield
Stage #1: 2-amino-thiazole-5-carboxylic acid ethyl ester With hydrogen bromide; sodium nitrite In water at 0℃;
Stage #2: With hydrogen bromide; copper(I) bromide In water at 0 - 20℃;
50%
Stage #1: 2-amino-thiazole-5-carboxylic acid ethyl ester With hydrogen bromide; sodium nitrite In water at 0℃; for 0.25h;
Stage #2: With hydrogen bromide; copper(I) bromide In water at 0 - 20℃; for 4h;
50.18%
Stage #1: 2-amino-thiazole-5-carboxylic acid ethyl ester With hydrogen bromide; sodium nitrite In water at 0℃; for 0.25h;
Stage #2: With copper(I) bromide In water at 0 - 20℃; for 4h;
50.18%
2-amino-thiazole-5-carboxylic acid ethyl ester
32955-21-8

2-amino-thiazole-5-carboxylic acid ethyl ester

2-nitrochalcone
53744-31-3, 7473-93-0

2-nitrochalcone

C21H17N3O3S

C21H17N3O3S

Conditions
ConditionsYield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; potassium carbonate In ethanol at 90℃; for 1h; Schlenk technique; Inert atmosphere;45%

32955-21-8Relevant articles and documents

Deprotection of N-Boc Groups under Continuous-Flow High-Temperature Conditions

Li, Bryan,Li, Ruizhi,Dorff, Peter,McWilliams, J. Christopher,Guinn, Robert M.,Guinness, Steven M.,Han, Lu,Wang, Ke,Yu, Shu

, p. 4846 - 4855 (2019/01/30)

The scope of thermolytic, N-Boc deprotection was studied on 26 compounds from the Pfizer compound library, representing a diverse set of structural moieties. Among these compounds, 12 substrates resulted in clean (≥95% product) deprotection, and an additional three compounds gave ≥90% product. The thermal de-Boc conditions were found to be compatible with a large number of functional groups. A combination of computational modeling, statistical analysis, and kinetic model fitting was used to support an initial, slow, and concerted proton transfer with release of isobutylene, followed by a rapid decarboxylation. A strong correlation was found to exist between the electrophilicity of the N-Boc carbonyl group and the reaction rate.

Synthetic method of Dasatinib intermediate

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Paragraph 0034; 0035, (2017/02/02)

The invention discloses a synthetic method of a Dasatinib intermediate. The method comprises the steps that compound 3-alkoxy acrylate shown in formula I, urea and potassium sulphide are subjected to contact reaction under the catalysis of nanometer copper powder to obtain Dasatinib intermediate 2-amino-thiazole-5-formate, wherein R1 and R2 are methyl, ethyl or propyl independently. According to the method for preparing the Dasatinib intermediate, the conditions are mild, the yield is effectively improved, pollution caused by bromine treatment to environment is reduced, and meanwhile the production cost is reduced due to the fact that cheap raw material urea is adopted.

The synthesis of 3-pyrazinyl-imidazo[1,2-a]pyridines from a vinyl ether

Collins, Michael Raymond,Huang, Qinhua,Ornelas, Martha A.,Scales, Stephanie A.

scheme or table, p. 3528 - 3530 (2010/08/22)

A new method has been developed for the synthesis of 3-pyrazinyl-imidazo[1, 2-a]pyridines. 2-Chloro-6-[(Z)-2-ethoxyethenyl]pyrazine was treated with N-bromosuccinimide in dioxane-water to generate the 2-bromo-2-(6-chloropyrazin- 2-yl)-1-ethoxyethanol intermediate. In a subsequent one-pot step, optional treatment with various 2-aminopyridines provided the cyclized 3-pyrazinyl-imidazo[1,2-a]pyridines in 31-76% yields.

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