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3430-19-1 Usage

Uses

3-Amino-5-methylpyridine is an important intermediate in organic synthesis, mainly used in pharmaceutical intermediates, organic synthesis, organic solvents, and can also be used in the production of dyes, pesticides and spices.

Synthesis

3-Amino-5-methylpyridine can be obtained by condensation reaction and decarboxylation reaction of diethyl malonate, sodium, 3-nitro-5-chloropyridine, and then reduction reaction.

Check Digit Verification of cas no

The CAS Registry Mumber 3430-19-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,4,3 and 0 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 3430-19:
(6*3)+(5*4)+(4*3)+(3*0)+(2*1)+(1*9)=61
61 % 10 = 1
So 3430-19-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H8N2/c1-5-2-6(7)4-8-3-5/h2-4H,7H2,1H3

3430-19-1 Well-known Company Product Price

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  • Aldrich

  • (684856)  3-Amino-5-methylpyridine  97%

  • 3430-19-1

  • 684856-250MG

  • 425.88CNY

  • Detail
  • Aldrich

  • (684856)  3-Amino-5-methylpyridine  97%

  • 3430-19-1

  • 684856-1G

  • 933.66CNY

  • Detail

3430-19-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Methylpyridin-3-amine

1.2 Other means of identification

Product number -
Other names 3-aMine-5-Methylpyridine

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:3430-19-1 SDS

3430-19-1Synthetic route

5-methylpyridinylcarboxamide
70-57-5

5-methylpyridinylcarboxamide

5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

Conditions
ConditionsYield
With potassium hydroxide; bromine 1.) RT, 1 h, 2.) 70 deg C, 15 min;67%
With sodium hydroxide; bromine In tetrahydrofuran at 5 - 70℃; Hoffmann rearrangement;
2-amino-3-methyl-5-nitropyridine
18344-51-9

2-amino-3-methyl-5-nitropyridine

5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

Conditions
ConditionsYield
With hydrazine In water at 110 - 120℃; for 5h;45%
Multi-step reaction with 3 steps
1: calcium chloride; aqueous sodium nitrite solution; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser
2: phosphoryl chloride
3: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation
View Scheme
Multi-step reaction with 2 steps
1: calcium chloride; aqueous sodium nitrite solution; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser
2: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation
View Scheme
5-Methyl-3-nitro-2-aminopyridine
7598-26-7

5-Methyl-3-nitro-2-aminopyridine

5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

Conditions
ConditionsYield
With hydrazine In water at 110 - 120℃; for 5h;41%
2-chloro-3-methyl-5-nitropyridine
22280-56-4

2-chloro-3-methyl-5-nitropyridine

5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

Conditions
ConditionsYield
With palladium on activated charcoal; sodium acetate; acetic acid Hydrogenation;
3,5-Lutidine
591-22-0

3,5-Lutidine

5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 27 percent / potassium permanganate / H2O / 1.) from RT to 43 deg C, 5 h, 2.) 45 deg C, overnight
2: thionyl chloride / Heating
3: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C
4: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min
View Scheme
5-methylnicotinic acid
3222-49-9

5-methylnicotinic acid

5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / Heating
2: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C
3: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min
View Scheme
5-methyl-nicotinic acid chloride
884494-95-5

5-methyl-nicotinic acid chloride

5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C
2: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min
View Scheme
3-methylpyridin-2-ylamine
1603-40-3

3-methylpyridin-2-ylamine

5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2SO4; HNO3
2: calcium chloride; aqueous sodium nitrite solution; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser
3: phosphoryl chloride
4: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation
View Scheme
Multi-step reaction with 3 steps
1: H2SO4; HNO3
2: calcium chloride; aqueous sodium nitrite solution; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser
3: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation
View Scheme
2-hydroxy-3-methyl-5-nitropyridine
21901-34-8

2-hydroxy-3-methyl-5-nitropyridine

5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosphoryl chloride
2: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation
View Scheme
2-bromo-3-methyl-5-nitropyridine
23132-21-0

2-bromo-3-methyl-5-nitropyridine

5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol
5-bromo-3-picoline
3430-16-8

5-bromo-3-picoline

5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); ammonia; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine; sodium t-butanolate In 1,4-dioxane for 24h; Reagent/catalyst;86 %Chromat.
3-chloro-5-nitropyridine
22353-33-9

3-chloro-5-nitropyridine

5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl N-(5-methylpyridin-3-yl)carbamate
631910-23-1

tert-butyl N-(5-methylpyridin-3-yl)carbamate

Conditions
ConditionsYield
Stage #1: 5-methylpyridin-3-amine With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.25h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃;
88%
With sodium hexamethyldisilazane In tetrahydrofuran at 20℃;88%
Stage #1: 5-methylpyridin-3-amine With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.25h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃;
88%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

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

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

2-[4-(2-bromobenzoyl)phenoxy]-N-(5-methylpyridin-3-yl)acetamide

2-[4-(2-bromobenzoyl)phenoxy]-N-(5-methylpyridin-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℃;86%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

N-Benzyloxycarbonyl-L-proline
1148-11-4

N-Benzyloxycarbonyl-L-proline

benzyl (S)-2-((5-methylpyridin-3-yl)carbamoyl)pyrrolidine-1-carboxylate

benzyl (S)-2-((5-methylpyridin-3-yl)carbamoyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: N-Benzyloxycarbonyl-L-proline With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 5-methylpyridin-3-amine In tetrahydrofuran at 0 - 70℃; for 25h; Inert atmosphere;
81%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

2,2,2-trifluoro-N-(5-methylpyridin-3-yl)acetamide

2,2,2-trifluoro-N-(5-methylpyridin-3-yl)acetamide

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;79%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

1,3-bis(5-methylpyridin-3-yl)urea
1387638-53-0

1,3-bis(5-methylpyridin-3-yl)urea

Conditions
ConditionsYield
In toluene at 20 - 80℃;75%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

ethyl acetoacetate
141-97-9

ethyl acetoacetate

N-(5-methylpyridin-3-yl)-3-oxobutanamide

N-(5-methylpyridin-3-yl)-3-oxobutanamide

Conditions
ConditionsYield
With sodium hydroxide In toluene at 100℃; for 10h;75%
In toluene at 100℃; for 10h;75%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

phenyl chloroformate
1885-14-9

phenyl chloroformate

(5-methyl-pyridin-3-yl)-carbamic acid phenyl ester
438190-95-5

(5-methyl-pyridin-3-yl)-carbamic acid phenyl ester

Conditions
ConditionsYield
With pyridine In tetrahydrofuran71%
With pyridine In tetrahydrofuran at 0℃;71%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

suberic acid monomethyl ester
3946-32-5

suberic acid monomethyl ester

methyl 8-((5-methylpyridin-3-yl)amino)-8-oxooctanoate

methyl 8-((5-methylpyridin-3-yl)amino)-8-oxooctanoate

Conditions
ConditionsYield
With N,N,N'N'-tetramethyl-1,3-propanediamine; boric acid In 1,3,5-trimethyl-benzene at 164℃; for 7h; Dean-Stark; Inert atmosphere; Green chemistry; regiospecific reaction;70%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

4-chloro-7-nitroisobenzofuran-1,3-dione

4-chloro-7-nitroisobenzofuran-1,3-dione

4-chloro-2-(5-methylpyridin-3-yl)-7-nitroisoindoline-1,3-dione

4-chloro-2-(5-methylpyridin-3-yl)-7-nitroisoindoline-1,3-dione

Conditions
ConditionsYield
With acetic acid at 120℃; for 12h;64.5%
In acetic acid for 18h; Reflux;
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}benzoic acid
1027256-79-6

3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}benzoic acid

3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}-N-(5-methylpyridin-3-yl)benzamide
1027253-93-5

3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}-N-(5-methylpyridin-3-yl)benzamide

Conditions
ConditionsYield
With 4-pyrrolidin-1-ylpyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 17h;61%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

(R)-(2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3:3,4]benzo[1,2-d]thiazol-7-yl)methyl carbonochloridate

(R)-(2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2,3:3,4]benzo[1,2-d]thiazol-7-yl)methyl carbonochloridate

(R)-(2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2’,3‘:3,4]benzo[1 ,2-d]thiazol-7-yl)methyl (5-methylpyridin-3-yl)carbamate

(R)-(2-(2-methoxy-7-methylquinoxalin-5-yl)-4-methyl-7,8-dihydro-[1,4]dioxino[2’,3‘:3,4]benzo[1 ,2-d]thiazol-7-yl)methyl (5-methylpyridin-3-yl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; carbonic acid dimethyl ester In tetrahydrofuran; dichloromethane at 20℃;53.9%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

4-(((4-(tert-butyl)phenyl)sulfonamido)methyl)benzoic acid

4-(((4-(tert-butyl)phenyl)sulfonamido)methyl)benzoic acid

4-({[(4-tert-butylphenyl)sulfonyl]amino}methyl)-N-(5-methyl-3-pyridinyl)benzamide

4-({[(4-tert-butylphenyl)sulfonyl]amino}methyl)-N-(5-methyl-3-pyridinyl)benzamide

Conditions
ConditionsYield
Stage #1: 4-(((4-(tert-butyl)phenyl)sulfonamido)methyl)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 20 - 66℃; for 3h;
Stage #2: 5-methylpyridin-3-amine With pyridine at 20℃; for 16h;
50%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

2,4-dibromo-butyryl bromide
52412-07-4

2,4-dibromo-butyryl bromide

3-bromo-1-(5-methylpyridin-3-yl)-2-oxopyrrolidine

3-bromo-1-(5-methylpyridin-3-yl)-2-oxopyrrolidine

Conditions
ConditionsYield
Stage #1: 5-methylpyridin-3-amine; 2,4-dibromo-butyryl bromide In dichloromethane at 0 - 20℃; for 3h;
Stage #2: With sodium hydroxide In dichloromethane; water at 20℃; for 3h;
49.2%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

(R)-(4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7 8-dihydro-[1,4]dioxino[2',3':3,4]benzo[1,2-d]thiazol-7-yl)methyl carbonochloridate

(R)-(4-chloro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7 8-dihydro-[1,4]dioxino[2',3':3,4]benzo[1,2-d]thiazol-7-yl)methyl carbonochloridate

(R)-(4-chloro-2-(2,7-dimethylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2',3':3,4]benzo[1,2-d]thiazol-7-yl)methyl (5-methylpyridin-3-yl)carbamate

(R)-(4-chloro-2-(2,7-dimethylquinoxalin-5-yl)-7,8-dihydro-[1,4]dioxino[2',3':3,4]benzo[1,2-d]thiazol-7-yl)methyl (5-methylpyridin-3-yl)carbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane; toluene at 20℃; for 0.5h;46.3%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(4S)-7-(2-methylpyridin-4-yl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine

(4S)-7-(2-methylpyridin-4-yl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine

(9S)-N-(5-methylpyridin-3-yl)-5-(2-methylpyridin-4-yl)-1,6,8-triazatricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-8-carboxamide

(9S)-N-(5-methylpyridin-3-yl)-5-(2-methylpyridin-4-yl)-1,6,8-triazatricyclo[7.2.1.02,7]dodeca-2(7),3,5-triene-8-carboxamide

Conditions
ConditionsYield
Stage #1: 5-methylpyridin-3-amine; bis(trichloromethyl) carbonate; (4S)-7-(2-methylpyridin-4-yl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine In tetrahydrofuran at 30℃; for 1h;
Stage #2: 5-methylpyridin-3-amine With triethylamine at 30 - 65℃; for 16h;
45%
Stage #1: bis(trichloromethyl) carbonate; (4S)-7-(2-methylpyridin-4-yl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine In tetrahydrofuran at 30℃; for 1h;
Stage #2: 5-methylpyridin-3-amine With triethylamine In tetrahydrofuran at 65℃; for 16h;
45%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

1-(5-(4,6-dichloropyrimidin-2-yl)-2-methylpiperidin-1-yl)ethan-1-one

1-(5-(4,6-dichloropyrimidin-2-yl)-2-methylpiperidin-1-yl)ethan-1-one

(+/-)-cis-1-(5-(4-chloro-6-((5-methylpyridin-3-yl)amino)pyrimidin-2-yl)-2-methylpiperidin-1-yl)ethan-1-one

(+/-)-cis-1-(5-(4-chloro-6-((5-methylpyridin-3-yl)amino)pyrimidin-2-yl)-2-methylpiperidin-1-yl)ethan-1-one

Conditions
ConditionsYield
Stage #1: 5-methylpyridin-3-amine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: 1-(5-(4,6-dichloropyrimidin-2-yl)-2-methylpiperidin-1-yl)ethan-1-one In tetrahydrofuran at 20℃; for 16h;
45%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(S)-N-[1-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine
1027255-35-1

(S)-N-[1-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine

N-(3-{(1S)-1-[(6-chloropyrazin-2-yl)amino]ethyl}phenyl)-N'-(5-methylpyridin-3-yl)urea
1027253-94-6

N-(3-{(1S)-1-[(6-chloropyrazin-2-yl)amino]ethyl}phenyl)-N'-(5-methylpyridin-3-yl)urea

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; (S)-N-[1-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine With sodium hydrogencarbonate In dichloromethane; water for 3h;
Stage #2: 5-methylpyridin-3-amine In dichloromethane; water for 17h;
42%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

(R)-(5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrobenzofuro[5,4-d]thiazol-7-yl)methyl carbonochloridate

(R)-(5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrobenzofuro[5,4-d]thiazol-7-yl)methyl carbonochloridate

(R)-(5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrobenzofuro[5,4-d]thiazol-7-yl)methyl (5-methoxypyridin-3-yl)carbamate

(R)-(5-fluoro-2-(2-methoxy-7-methylquinoxalin-5-yl)-7,8-dihydrobenzofuro[5,4-d]thiazol-7-yl)methyl (5-methoxypyridin-3-yl)carbamate

Conditions
ConditionsYield
With pyridine; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h;39.6%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

iodobenzene
591-50-4

iodobenzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

3-methyl-5-phenylpyridine
10477-94-8

3-methyl-5-phenylpyridine

Conditions
ConditionsYield
Stage #1: 5-methylpyridin-3-amine; bis(pinacol)diborane With tert.-butylnitrite In acetonitrile at 80℃; for 2h;
Stage #2: iodobenzene With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere;
35%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

2-methoxycarbonylbenzenesulfonyl chloride
26638-43-7

2-methoxycarbonylbenzenesulfonyl chloride

methyl 2-{[(5-methylpyridin-3-yl)amino]sulfonyl}benzoate
931126-93-1

methyl 2-{[(5-methylpyridin-3-yl)amino]sulfonyl}benzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1h;34%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(S)-6-(3-(3-fluoropyrrolidin-1-yl)phenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

(S)-6-(3-(3-fluoropyrrolidin-1-yl)phenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

(S)-6-(3-(3-fluoropyrrolidin-1-yl)phenyl)-2,2-dimethyl-N-(5-methylpyridin-3-yl)-2H-pyrido[3,2-b][1,4]oxazine-4(3H)-carboxamide
1303585-09-2

(S)-6-(3-(3-fluoropyrrolidin-1-yl)phenyl)-2,2-dimethyl-N-(5-methylpyridin-3-yl)-2H-pyrido[3,2-b][1,4]oxazine-4(3H)-carboxamide

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; (S)-6-(3-(3-fluoropyrrolidin-1-yl)phenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine With triethylamine In tetrahydrofuran at 20℃; for 1.5h;
Stage #2: 5-methylpyridin-3-amine In tetrahydrofuran at 60℃; for 18h;
31%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

7-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydro-1,8-naphthyridine
1303588-28-4

7-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydro-1,8-naphthyridine

N-(5-methylpyridin-3-yl)-7-(3-(trifluoromethyl)phenyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide
1303583-59-6

N-(5-methylpyridin-3-yl)-7-(3-(trifluoromethyl)phenyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; 7-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydro-1,8-naphthyridine With triethylamine In tetrahydrofuran at 30℃; for 0.5h; Inert atmosphere;
Stage #2: 5-methylpyridin-3-amine In tetrahydrofuran at 60℃; for 18h; Inert atmosphere;
27%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

A

3-amino-2,6-dibromo-5-methylpyridine
126325-51-7

3-amino-2,6-dibromo-5-methylpyridine

B

3-amino-2-bromo-5-methylpyridine
34552-14-2

3-amino-2-bromo-5-methylpyridine

C

3-amino-2,4,6-tribromo-5-methylpyridine

3-amino-2,4,6-tribromo-5-methylpyridine

Conditions
ConditionsYield
With hydrogen bromide; dihydrogen peroxide at 70℃; for 1h; Product distribution;A 26%
B 6%
C 0.5%
With hydrogen bromide; dihydrogen peroxide at 70℃; for 1h;A 26%
B 6%
C 0.5%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

1-(3-chloro-5-methyl-5H-chromeno[4,3-c]pyridin-8-yl)pyrrolidin-2-one

1-(3-chloro-5-methyl-5H-chromeno[4,3-c]pyridin-8-yl)pyrrolidin-2-one

1-(5-methyl-3-((5-methylpyridin-3-yl)amino)-5H-chromeno[4,3-c]pyridin8-yl)pyrrolidin-2-one

1-(5-methyl-3-((5-methylpyridin-3-yl)amino)-5H-chromeno[4,3-c]pyridin8-yl)pyrrolidin-2-one

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; caesium carbonate In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;22%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

2,2-dimethyl-6-(3-(pyrrolidin-1-ylmethyl)phenyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine
1303588-19-3

2,2-dimethyl-6-(3-(pyrrolidin-1-ylmethyl)phenyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

2,2-dimethyl-N-(5-methylpyridin-3-yl)-6-(3-(pyrrolidin-1-ylmethyl)phenyl)-2H-pyrido[3,2-b][1,4]oxazine-4(3H)-carboxamide
1303584-47-5

2,2-dimethyl-N-(5-methylpyridin-3-yl)-6-(3-(pyrrolidin-1-ylmethyl)phenyl)-2H-pyrido[3,2-b][1,4]oxazine-4(3H)-carboxamide

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; 2,2-dimethyl-6-(3-(pyrrolidin-1-ylmethyl)phenyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine With triethylamine In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: 5-methylpyridin-3-amine In tetrahydrofuran at 60℃;
20%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

1-[(4-bromophenyl)carbamoylamino]cyclopentanecarboxylic acid

1-[(4-bromophenyl)carbamoylamino]cyclopentanecarboxylic acid

1-[(4-bromophenyl)carbamoylamino]-N-(5-methyl-3-pyridyl)cyclopentanecarboxamide

1-[(4-bromophenyl)carbamoylamino]-N-(5-methyl-3-pyridyl)cyclopentanecarboxamide

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 20℃;20%
5-methylpyridin-3-amine
3430-19-1

5-methylpyridin-3-amine

thiophosgene
463-71-8

thiophosgene

3-isothiocyanato-5-methylpyridine

3-isothiocyanato-5-methylpyridine

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water at 0℃; for 2h;19%

3430-19-1Relevant articles and documents

Synthesis method of 3-bromo-5-methylpyridine

-

Paragraph 0025, (2017/10/07)

The invention relates to the field of organic chemistry and particularly provides a synthesis method of 3-bromo-5-methylpyridine. The synthesis method includes the steps of: 1) performing a reaction to diethyl malonate and alkaline metal to generate a salt, and dropwise adding a toluene solution of 3-nitro-5-chloropyridine to perform a condensation reaction, and decarboxylating the product under an acidic condition to obtain 3-nitro-5-methylpyridine; 2) performing hydrogenation reduction to the 3-nitro-5-methylpyridine with Pd/C as a catalyst and methanol as a solvent, performing suction filtration and concentrating a filtrate to prepare 3-amino-5-methylpyridine; and 3) performing a reaction to the 3-amino-5-methylpyridine with an acid to generate a salt, and cooling the salt to -10 - 0 DEG C, dropwise adding liquid bromine, and then dropwise adding a sodium nitrite water solution, regulating the pH value of the solution to alkalinity and performing extraction, drying and concentration to obtain the 3-bromo-5-methylpyridine. The synthesis method is mild in reaction conditions, is high in yield, employs easy-to-obtained raw materials, is low in cost, is short in process route and has industrial prospect.

COMPOSITIONS AND THERAPEUTIC USES OF IKK-RELATED KINASE EPSILON AND TANKBINDING KINASE 1 INHIBITORS

-

Page/Page column 75, (2012/11/06)

The invention relates to compounds, pharmaceutical compositions and medicaments comprising such compounds, and the use of these compounds, compositions, and medicaments in methods of treating diseases and disorders.

Structure-activity studies of novel cyanoguanidine ATP-sensitive potassium channel openers for the treatment of overactive bladder

Perez-Medrano, Arturo,Brune, Michael E.,Buckner, Steven A.,Coghlan, Michael J.,Fey, Thomas A.,Gopalakrishnan, Murali,Gregg, Robert J.,Kort, Michael E.,Scott, Victoria E.,Sullivan, James P.,Whiteaker, Kristi L.,Carroll, William A.

, p. 6265 - 6273 (2008/04/05)

A series of novel cyanoguanidine derivatives was designed and synthesized. Condensation of N-(1-benzotriazol-1-yl-2,2-dichloropropyl)-substituted benzamides with N-(substituted-pyridin-3-yl)-N′-cyanoguanidines furnished N-{2,2-dichloro-1-[N′-(substituted-pyridin-3-yl)-N′-cyanoguanidino] propyl}-substituted benzamide derivatives. These agents were glyburide-reversible potassium channel openers and hyperpolarized human bladder cells as assessed by the FLIPR membrane potential dye (KATP-FMP). These compounds were also potent full agonists in relaxing electrically stimulated pig bladder strips, an in vitro model of overactive bladder. The most active compound 9 was evaluated for in vivo efficacy and selectivity in a pig model of bladder instability. Preliminary pharmacokinetic studies in dog demonstrated excellent oral bioavailability and a t1/2 of 15 h. The synthesis, SAR studies, and biological properties of these agents are discussed.

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