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22889-78-7

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22889-78-7 Usage

Chemical Properties

Crystalline powder

Uses

4-Amino-3,5-dichloropyridine is a metabolite of the selective phosphodiesterase 4 (PDE4) inhibitor, Roflumilast (R639700).

Check Digit Verification of cas no

The CAS Registry Mumber 22889-78-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,8,8 and 9 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 22889-78:
(7*2)+(6*2)+(5*8)+(4*8)+(3*9)+(2*7)+(1*8)=147
147 % 10 = 7
So 22889-78-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H4Cl2N2/c6-3-1-9-2-4(7)5(3)8/h1-2H,(H2,8,9)/p+1

22889-78-7 Well-known Company Product Price

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  • Alfa Aesar

  • (B24725)  4-Amino-3,5-dichloropyridine, 98+%   

  • 22889-78-7

  • 5g

  • 647.0CNY

  • Detail
  • Alfa Aesar

  • (B24725)  4-Amino-3,5-dichloropyridine, 98+%   

  • 22889-78-7

  • 25g

  • 1552.0CNY

  • Detail
  • Alfa Aesar

  • (B24725)  4-Amino-3,5-dichloropyridine, 98+%   

  • 22889-78-7

  • 100g

  • 4955.0CNY

  • Detail

22889-78-7SDS

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 4-Amino-3,5-dichloropyridine

1.2 Other means of identification

Product number -
Other names aminodichloropyridine

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:22889-78-7 SDS

22889-78-7Synthetic route

4-aminopyridine
504-24-5

4-aminopyridine

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

Conditions
ConditionsYield
Stage #1: 4-aminopyridine With hydrogenchloride; dihydrogen peroxide In water at 10 - 72℃; for 3.25h;
Stage #2: With sodium hydroxide In water at 45℃; for 0.5h; pH=9 - 10; Reagent/catalyst; Temperature;
92.7%
With hydrogenchloride; dihydrogen peroxide
With aqueous hydrogen peroxide In concentrated hydrochloric acid
3,3,5,5-tetrachloropiperidin-4-one

3,3,5,5-tetrachloropiperidin-4-one

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

Conditions
ConditionsYield
With ammonia In methanol at 40 - 45℃; for 4h; Autoclave;89.7%
3,5-dichloropyridine-4-carbonitrile
153463-65-1

3,5-dichloropyridine-4-carbonitrile

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

Conditions
ConditionsYield
With lithium amide In ammonia 0 deg C to RT;54%
4-amino-3-chloropyridine
19798-77-7

4-amino-3-chloropyridine

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide
3,4,5-trichloropyridine
33216-52-3

3,4,5-trichloropyridine

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

Conditions
ConditionsYield
With ammonium hydroxide at 150℃; im Rohr;
4-amino-3,5-dichloro-pyridine-2-carboxylic acid
17122-17-7

4-amino-3,5-dichloro-pyridine-2-carboxylic acid

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

Conditions
ConditionsYield
Erhitzen ueber den Schmelzpunkt;
3.5-dichloro-4-amino-picolinic acid

3.5-dichloro-4-amino-picolinic acid

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

Conditions
ConditionsYield
beim Erhitzen ueber den Schmelzpunkt;
3,4,5-trichloropyridine
33216-52-3

3,4,5-trichloropyridine

ammonia
7664-41-7

ammonia

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

Conditions
ConditionsYield
at 150℃; im Rohr;
4-aminopyridine
504-24-5

4-aminopyridine

hydrogenchloride
7647-01-0

hydrogenchloride

water
7732-18-5

water

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

hydrogenchloride
7647-01-0

hydrogenchloride

4-(nitroamino)pyridine
26482-55-3

4-(nitroamino)pyridine

A

4-Chloropyridine
626-61-9

4-Chloropyridine

B

3,4,5-trichloropyridine
33216-52-3

3,4,5-trichloropyridine

C

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

Conditions
ConditionsYield
at 100℃;
3-amino-4-chloropyridine
20511-15-3

3-amino-4-chloropyridine

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium nitrite; copper-powder; aqueous hydrochloric acid / Diazotization
2: aqueous NH3 / 190 °C
3: concentrated aqueous HCl; aqueous H2O2
View Scheme
3,4-dichloropyridine
55934-00-4

3,4-dichloropyridine

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous NH3 / 190 °C
2: concentrated aqueous HCl; aqueous H2O2
View Scheme
3-benzoyloxy-4-methoxybenzoyl chloride
144036-22-6

3-benzoyloxy-4-methoxybenzoyl chloride

A

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

B

N-(3,5-dichloropyrid-4-yl)-3-benzoyloxy-4-methoxybenzamide
159782-90-8

N-(3,5-dichloropyrid-4-yl)-3-benzoyloxy-4-methoxybenzamide

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

5-[5-{[(3,5-dichloropyridin-4-yl)amino]carbonyl}-2-(difluoromethoxy) phenoxy]pentanoic acid
1422361-76-9

5-[5-{[(3,5-dichloropyridin-4-yl)amino]carbonyl}-2-(difluoromethoxy) phenoxy]pentanoic acid

Conditions
ConditionsYield
With thionyl chloride In tetrahydrofuran; toluene96.45%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

2-(3-benzyloxy-propyl)-3,4-dimethoxy-benzoic acid
1006612-51-6

2-(3-benzyloxy-propyl)-3,4-dimethoxy-benzoic acid

2-(3-benzyloxy-propyl)-N-(3,5-dichloro-pyridin-4-yl)-3,4-dimethoxy-benzamide
1006612-52-7

2-(3-benzyloxy-propyl)-N-(3,5-dichloro-pyridin-4-yl)-3,4-dimethoxy-benzamide

Conditions
ConditionsYield
Stage #1: 2-(3-benzyloxy-propyl)-3,4-dimethoxy-benzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 40℃; for 2h;
Stage #2: 3,5-dichloro-4-aminopyridine With sodium hydride In tetrahydrofuran at 20 - 30℃; for 3.5h;
96%
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid
162401-62-9

3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

roflumilast
162401-32-3

roflumilast

Conditions
ConditionsYield
Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid With pyridine; 2,4,6-trinitrochlorobenzene In 1,4-dioxane at 20 - 35℃; for 3h; Industrial scale;
Stage #2: 3,5-dichloro-4-aminopyridine In 1,4-dioxane for 2h; Reagent/catalyst; Solvent; Temperature; Industrial scale;
95%
Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In dichloromethane at 0 - 20℃; for 3h;
Stage #2: 3,5-dichloro-4-aminopyridine In dichloromethane for 2h; Concentration;
91%
Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid With pivaloyl chloride; sodium carbonate In tetrahydrofuran at 25℃; for 2h;
Stage #2: 3,5-dichloro-4-aminopyridine In tetrahydrofuran at 50℃; for 4h; Temperature; Solvent; Reagent/catalyst;
64%
Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid With thionyl chloride In toluene Heating / reflux;
Stage #2: 3,5-dichloro-4-aminopyridine With sodium hydride In tetrahydrofuran for 1h; Cooling;
58.6%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

3-(difluoromethoxy)-4-(cyclopropylmethoxy)-benzoic acid
162401-69-6

3-(difluoromethoxy)-4-(cyclopropylmethoxy)-benzoic acid

roflumilast
162401-32-3

roflumilast

Conditions
ConditionsYield
Stage #1: 3-(difluoromethoxy)-4-(cyclopropylmethoxy)-benzoic acid With thionyl chloride In toluene for 2h; Reflux;
Stage #2: 3,5-dichloro-4-aminopyridine With sodium hydride In tetrahydrofuran at 15 - 20℃;
95%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

N-(3,5-dichloropyridin-4-yl)-3-phenylpropanamide
1370286-81-9

N-(3,5-dichloropyridin-4-yl)-3-phenylpropanamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;93%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h;93.3%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

4-nitrophenyl 8-methoxy-2,9-dimethyl-1-oxo-1,2,3,4-tetrahydro-β-carboline-5-carboxylate
893555-73-2

4-nitrophenyl 8-methoxy-2,9-dimethyl-1-oxo-1,2,3,4-tetrahydro-β-carboline-5-carboxylate

N-(3,5-dichloropyridin-4-yl)-2,9-dimethyl-8-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline-5-carboxamide

N-(3,5-dichloropyridin-4-yl)-2,9-dimethyl-8-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline-5-carboxamide

Conditions
ConditionsYield
With sodium hydride at 20℃; for 18h;90%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 18h;
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)(1H-imidazol-1-yl)methanone
1590361-85-5

(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)(1H-imidazol-1-yl)methanone

roflumilast
162401-32-3

roflumilast

Conditions
ConditionsYield
Stage #1: 3,5-dichloro-4-aminopyridine With cesium fluoride In dimethyl sulfoxide at 90℃; for 3h;
Stage #2: (3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)(1H-imidazol-1-yl)methanone In dimethyl sulfoxide at 90 - 95℃; for 6.5h; Reagent/catalyst;
88%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

p-nitrophenyl 4-difluormethoxy-8-nitrodibenzofuran carboxylic acid ester
883977-47-7

p-nitrophenyl 4-difluormethoxy-8-nitrodibenzofuran carboxylic acid ester

N-(3,5-dichloro-pyridin-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furane-1-carboxamide
685875-02-9

N-(3,5-dichloro-pyridin-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furane-1-carboxamide

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 25 - 35℃; for 1.83333 - 1.91667h;86%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

3,4-bis(cyclopropylmethoxy)benzoyl chloride
669001-67-6

3,4-bis(cyclopropylmethoxy)benzoyl chloride

3,4-bis(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl) benzamide

3,4-bis(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl) benzamide

Conditions
ConditionsYield
With sodium hydride In acetonitrile at -5 - 0℃; for 1h;85.3%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

C17H10F2N2O2S

C17H10F2N2O2S

3,5-dichloro-4-(4-difluoromethoxy-dibenzo[b,d]-thiophen-1-yl-carboxamido)pyridine

3,5-dichloro-4-(4-difluoromethoxy-dibenzo[b,d]-thiophen-1-yl-carboxamido)pyridine

Conditions
ConditionsYield
Stage #1: 3,5-dichloro-4-aminopyridine With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5h;
Stage #2: C17H10F2N2O2S In DMF (N,N-dimethyl-formamide)
85%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

3-cyclopentyloxy-4-methoxy benzoic acid chloride
144036-19-1

3-cyclopentyloxy-4-methoxy benzoic acid chloride

piclamilast
144035-83-6

piclamilast

Conditions
ConditionsYield
Stage #1: 3,5-dichloro-4-aminopyridine With potassium tert-butylate In toluene at 90℃; Green chemistry;
Stage #2: 3-cyclopentyloxy-4-methoxy benzoic acid chloride In toluene for 1h; Reagent/catalyst; Temperature; Solvent; Reflux; Green chemistry;
84%
With sodium hydride 1.) THF, 0.25 h, 2.) THF, RT, 0.5 h; Yield given. Multistep reaction;
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

7-methoxy-2-phenethyl-benzofuran-4-carbonyl chloride

7-methoxy-2-phenethyl-benzofuran-4-carbonyl chloride

7-methoxy-2-phenethyl-benzofuran-4-carboxylic acid (3,5-dichloropyridin-4-yl)-amide

7-methoxy-2-phenethyl-benzofuran-4-carboxylic acid (3,5-dichloropyridin-4-yl)-amide

Conditions
ConditionsYield
Stage #1: 3,5-dichloro-4-aminopyridine With sodium aluminum diethyl dihydride In tetrahydrofuran; toluene at 50℃; for 1h; Metallation;
Stage #2: 7-methoxy-2-phenethyl-benzofuran-4-carbonyl chloride In tetrahydrofuran; toluene at 50℃; for 2h; Acylation;
80%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

4-(difluoromethoxy)benzoyl chloride
57320-63-5

4-(difluoromethoxy)benzoyl chloride

N-(3,5-dichloro-4-pyridyl)-4-(difluoromethoxy)benzamide

N-(3,5-dichloro-4-pyridyl)-4-(difluoromethoxy)benzamide

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h; Reagent/catalyst;80%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)(1H-1,2,4-triazol-1-yl)methanone
1601300-21-3

(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)(1H-1,2,4-triazol-1-yl)methanone

roflumilast
162401-32-3

roflumilast

Conditions
ConditionsYield
Stage #1: 3,5-dichloro-4-aminopyridine With cesium fluoride In dimethyl sulfoxide at 90℃; for 3h;
Stage #2: (3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)(1H-1,2,4-triazol-1-yl)methanone In dimethyl sulfoxide at 90 - 95℃; for 3h;
79%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

4-methoxy-2-methylsulfanylpyrimidine-5-carboxylic acid
84332-06-9

4-methoxy-2-methylsulfanylpyrimidine-5-carboxylic acid

N-(3,5-dichloropyridin-4-yl)-4-methoxy-2-(methylthio)pyrimidine-5-carboxamide

N-(3,5-dichloropyridin-4-yl)-4-methoxy-2-(methylthio)pyrimidine-5-carboxamide

Conditions
ConditionsYield
Stage #1: 4-methoxy-2-methylsulfanylpyrimidine-5-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 5h;
Stage #2: 3,5-dichloro-4-aminopyridine With sodium hydride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2h;
75.06%
2-(cyclopentyloxy)-4-iodo-1-methoxybenzene
651023-32-4

2-(cyclopentyloxy)-4-iodo-1-methoxybenzene

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

13C-methyldiphenylsilanecarboxylic acid
1346220-47-0

13C-methyldiphenylsilanecarboxylic acid

C17(13)CH18Cl2N2O3
1346220-48-1

C17(13)CH18Cl2N2O3

Conditions
ConditionsYield
Stage #1: 13C-methyldiphenylsilanecarboxylic acid With potassium fluoride In toluene at 70℃; Inert atmosphere;
Stage #2: 2-(cyclopentyloxy)-4-iodo-1-methoxybenzene; 3,5-dichloro-4-aminopyridine With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; catacxium A In toluene at 70℃; for 21h; Inert atmosphere;
74%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde
151103-09-2

3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde

3,5-dichloro-N-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzylidene)pyridin-4-amine
1454574-39-0

3,5-dichloro-N-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzylidene)pyridin-4-amine

Conditions
ConditionsYield
Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With trifluoroacetic acid; trimethyl orthoformate In toluene at 20 - 30℃; Inert atmosphere; Reflux;
Stage #2: 3,5-dichloro-4-aminopyridine With trifluoroacetic acid In toluene at 40 - 110℃;
73%
Stage #1: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde With toluene-4-sulfonic acid; trimethyl orthoformate In toluene for 3h; Reflux;
Stage #2: 3,5-dichloro-4-aminopyridine With toluene-4-sulfonic acid In toluene at 70 - 80℃; for 30h; Reflux;
23%
With N,O-Bis(trimethylsilyl)trifluoroacetamide; toluene-4-sulfonic acid In acetonitrile for 48h; Reagent/catalyst; Reflux;70 %Chromat.
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

tert-butyl 4-(4-(2,5-dichloro-4-pyrimidinyl)amino-5-isopropoxy-2-methylphenyl)piperidine-1-carboxylate

tert-butyl 4-(4-(2,5-dichloro-4-pyrimidinyl)amino-5-isopropoxy-2-methylphenyl)piperidine-1-carboxylate

5-chloro-N2(3,5-dichloropyridin-4-yl)-N4(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)pyrimidine-2,4-diamine

5-chloro-N2(3,5-dichloropyridin-4-yl)-N4(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)pyrimidine-2,4-diamine

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 80℃;72.9%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

1-(4-fluorobenzyl)-7-azaindol-3-yl-glycoxylic acid chloride

1-(4-fluorobenzyl)-7-azaindol-3-yl-glycoxylic acid chloride

AWD-12-353

AWD-12-353

Conditions
ConditionsYield
Stage #1: 3,5-dichloro-4-aminopyridine With sodium hydride In tetrahydrofuran at -5 - 20℃; for 1h;
Stage #2: 1-(4-fluorobenzyl)-7-azaindol-3-yl-glycoxylic acid chloride In tetrahydrofuran at 0℃; for 4h; Product distribution / selectivity; Reflux;
72%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

C49H77N5O15S
1006612-69-6

C49H77N5O15S

C54H79Cl2N7O14S
1006612-25-4

C54H79Cl2N7O14S

Conditions
ConditionsYield
With water; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at -5 - 25℃; for 4h;70%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

4-amino-6-(3-bromophenyl)-2-ethylpyridazin-3(2H)-one
1229442-28-7

4-amino-6-(3-bromophenyl)-2-ethylpyridazin-3(2H)-one

1-(6-(3-bromophenyl)-2-ethyl-3-oxo-2,3-dihydropyridazin-4-yl)-3-(3,5-dichloropyridin-4-yl)urea
1229442-29-8

1-(6-(3-bromophenyl)-2-ethyl-3-oxo-2,3-dihydropyridazin-4-yl)-3-(3,5-dichloropyridin-4-yl)urea

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; 4-amino-6-(3-bromophenyl)-2-ethylpyridazin-3(2H)-one With triethylamine In dichloromethane for 3h; Inert atmosphere;
Stage #2: 3,5-dichloro-4-aminopyridine With sodium hydride In tetrahydrofuran at 20℃;
70%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

3,4,5-Trimethoxybenzoyl chloride
4521-61-3

3,4,5-Trimethoxybenzoyl chloride

N-(3,5-dichloropyridin-4-yl)-3,4,5-trimethoxybenzamide
1349175-46-7

N-(3,5-dichloropyridin-4-yl)-3,4,5-trimethoxybenzamide

Conditions
ConditionsYield
Stage #1: 3,5-dichloro-4-aminopyridine With potassium 2-methylbutan-2-olate In toluene at 90℃; for 0.5h;
Stage #2: for 0.5h; Reflux;
Stage #3: 3,4,5-Trimethoxybenzoyl chloride Further stages;
70%
Stage #1: 3,5-dichloro-4-aminopyridine With sodium hydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;
Stage #2: 3,4,5-Trimethoxybenzoyl chloride In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere;
54%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

C16H10F3N3O5
1009603-03-5

C16H10F3N3O5

7-methoxy-2-trifluoromethylpyrazolo[1,5-a]pyridine-4-carboxylic acid (3,5-dichloro pyridin-4-yl)amide
1009601-54-0

7-methoxy-2-trifluoromethylpyrazolo[1,5-a]pyridine-4-carboxylic acid (3,5-dichloro pyridin-4-yl)amide

Conditions
ConditionsYield
Stage #1: 3,5-dichloro-4-aminopyridine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;
Stage #2: C16H10F3N3O5 In N,N-dimethyl-formamide at 0 - 20℃; for 3h;
70%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

C16H10F3N3O5

C16H10F3N3O5

N-(3,5-dichloropyridin-4-yl)-7-methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine-3-carboxamide
1454802-94-8

N-(3,5-dichloropyridin-4-yl)-7-methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine-3-carboxamide

Conditions
ConditionsYield
Stage #1: 3,5-dichloro-4-aminopyridine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;
Stage #2: C16H10F3N3O5 In N,N-dimethyl-formamide at 0 - 20℃; for 3h;
70%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

methyl 4-(5-((3,5-dichloropyridin-4-yl)carbamoyl)-2-(difluoromethoxy)phenoxy)benzoate
1422361-57-6

methyl 4-(5-((3,5-dichloropyridin-4-yl)carbamoyl)-2-(difluoromethoxy)phenoxy)benzoate

Conditions
ConditionsYield
70%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

C13H10BrN3O2

C13H10BrN3O2

1-(6-(3-bromophenyl)-2-ethyl-3-oxo-2,3-dihydropyridazin-4-yl)-3-(3,5-dichloropyridin-4-yl)urea
1229442-29-8

1-(6-(3-bromophenyl)-2-ethyl-3-oxo-2,3-dihydropyridazin-4-yl)-3-(3,5-dichloropyridin-4-yl)urea

Conditions
ConditionsYield
Stage #1: 3,5-dichloro-4-aminopyridine With sodium hydride In tetrahydrofuran for 2.5h;
Stage #2: C13H10BrN3O2 In tetrahydrofuran at 20℃;
70%
3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

2-benzyl-7-methoxy-benzofuran-4-carbonyl chloride

2-benzyl-7-methoxy-benzofuran-4-carbonyl chloride

2-benzyl-7-methoxy-benzofuran-4-carboxylic acid (3,5-dichloropyridin-4-yl)-amide

2-benzyl-7-methoxy-benzofuran-4-carboxylic acid (3,5-dichloropyridin-4-yl)-amide

Conditions
ConditionsYield
Stage #1: 3,5-dichloro-4-aminopyridine With sodium aluminum diethyl dihydride In tetrahydrofuran; toluene at 50℃; for 1h; Metallation;
Stage #2: 2-benzyl-7-methoxy-benzofuran-4-carbonyl chloride In tetrahydrofuran; toluene at 50℃; for 2h; Acylation;
67%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

3,5-dichloro-4-aminopyridine
22889-78-7

3,5-dichloro-4-aminopyridine

3,5-dichloro-4-(1H-pyrrol-1-yl)pyridine

3,5-dichloro-4-(1H-pyrrol-1-yl)pyridine

Conditions
ConditionsYield
With acetic acid at 120℃; for 0.333333h; Inert atmosphere;63%

22889-78-7Relevant articles and documents

Preparation method of pyridine derivative (by machine translation)

-

Paragraph 0111-0114, (2019/12/02)

To the method, piperidine-4-one hydrochloride is used as a raw material, and a series of pyridine derivatives are obtained through halogenation reaction and elimination reaction. The reaction is eliminated by reacting piperidine-4-one hydrochloride with a specific amount of the 3,5 - halogenating agent in a halogenation 3, 3, 5 - reaction with a halogen-3, 3, 5, 5 - based reaction, followed by reaction with a pyridine derivative of a hydroxyl group, an amino group 4 - or a dimethylamino group, respectively, by eliminating the reaction with a different kind of basic agent. The method is simple and convenient to operate, mild in condition, short in technological process, low in waste water yield, environment-friendly, low in cost and beneficial to green industrial production of the pyridine derivative. (by machine translation)

COMPOUNDS CONTAINING PHENYL LINKED TO ARYL OR HETEROARYL BY AN ALIPHATIC- OR HETEROATOM-CONTAINING LINKING GROUP

-

, (2008/06/13)

This invention is directed to the pharmaceutical use of phenyl compounds, which are linked to an aryl moiety by various linkages, for inhibiting tumor necrosis factor. The invention is also directed to the compounds, their preparation and pharmaceutical compositions containing these compounds. Furthermore, this invention is directed to the pharmaceutical use of the compounds for inhibiting cyclic AMP phosphodiesterase

SUBSTITUTED AROMATIC COMPOUNDS AS c.AMP PHOSPHODIESTERASE- AND TNF-INHIBITORS

-

, (2008/06/13)

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