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943606-84-6

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943606-84-6 Usage

General Description

The chemical compound 1-chloro-6-methyl-5-nitroisoquinoline is an organic substance that is part of the isoquinoline family, which is often used in pharmaceuticals and various chemical researches due to their biological activity. The compound has a specific molecular formula of C11H8ClN3O2. It contains atoms of carbon, hydrogen, chlorine, nitrogen, and oxygen, which are bonded in a certain sequence to form a stable structure. The presence of a nitro and a chlorine group on the isoquinoline ring indicates that the compound might exhibit unique chemical and physical properties, although it is not commonly used and its applications are not well documented. Further research and experiment are necessary to fully understand its potential uses.

Check Digit Verification of cas no

The CAS Registry Mumber 943606-84-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 9,4,3,6,0 and 6 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 943606-84:
(8*9)+(7*4)+(6*3)+(5*6)+(4*0)+(3*6)+(2*8)+(1*4)=186
186 % 10 = 6
So 943606-84-6 is a valid CAS Registry Number.

943606-84-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-chloro-6-methyl-5-nitroisoquinoline

1.2 Other means of identification

Product number -
Other names -

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:943606-84-6 SDS

943606-84-6Synthetic route

6-methyl-5-nitroisoquinoline 2-oxide
943606-83-5

6-methyl-5-nitroisoquinoline 2-oxide

1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

Conditions
ConditionsYield
With trichlorophosphate In chloroform at 70℃; for 3h;96%
With trichlorophosphate In 1,2-dichloro-ethane at 70℃; for 3h;86%
With trichlorophosphate In 1,2-dichloro-ethane Reflux;55%
With trichlorophosphate In 1,2-dichloro-ethane Reflux;55%
With trichlorophosphate In 1,2-dichloro-ethane at 70℃;0.88 g
6-methyl-5-nitroisoquinoline
188121-31-5

6-methyl-5-nitroisoquinoline

1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

Conditions
ConditionsYield
With trichlorophosphate In 1,2-dichloro-ethane Reflux;55%
With trichlorophosphate In 1,2-dichloro-ethane for 7h; Reflux;55%
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
2: trichlorophosphate / 1,2-dichloro-ethane / Reflux
View Scheme
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
2: trichlorophosphate / 1,2-dichloro-ethane / Reflux
View Scheme
Multi-step reaction with 2 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 °C
2: trichlorophosphate / 1,2-dichloro-ethane / 3 h / 70 °C
View Scheme
6-methylisoquinoline N-oxide
70810-28-5

6-methylisoquinoline N-oxide

1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

Conditions
ConditionsYield
With potassium nitrate; trichlorophosphate In chloroform; sulfuric acid
6-methylisoquinoline
42398-73-2

6-methylisoquinoline

1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid; potassium nitrate / 0 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
3: trichlorophosphate / 1,2-dichloro-ethane / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium nitrate; sulfuric acid / 0 °C
2: trichlorophosphate / 1,2-dichloro-ethane / Reflux
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid; potassium nitrate / 3 h / 0 °C
2: trichlorophosphate / 1,2-dichloro-ethane / 7 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid; potassium nitrate / 0 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
3: trichlorophosphate / 1,2-dichloro-ethane / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid; potassium nitrate / 1.5 h / 0 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 °C
3: trichlorophosphate / 1,2-dichloro-ethane / 3 h / 70 °C
View Scheme
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: chloroform / 90 °C
2.1: chloroformic acid ethyl ester; triethyl phosphite / chloroform / 24 h / 0 - 20 °C
2.2: 0 °C / Reflux
3.1: sulfuric acid; potassium nitrate / 0 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
5.1: trichlorophosphate / 1,2-dichloro-ethane / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: chloroform / 90 °C
1.2: 24 h / 0 - 20 °C
1.3: 0 - 20 °C / Reflux
2.1: potassium nitrate; sulfuric acid / 0 °C
3.1: trichlorophosphate / 1,2-dichloro-ethane / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: chloroform / 90 °C
1.2: 24 h / 0 - 20 °C
1.3: 12 h / 0 °C / Reflux
2.1: sulfuric acid; potassium nitrate / 3 h / 0 °C
3.1: trichlorophosphate / 1,2-dichloro-ethane / 7 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: chloroform / 90 °C
1.2: 24 h / 0 - 20 °C
1.3: 0 °C / Reflux
2.1: sulfuric acid; potassium nitrate / 0 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
4.1: trichlorophosphate / 1,2-dichloro-ethane / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: chloroform / 22 - 65 °C
1.2: 23 h / -3 - 20 °C
1.3: 10.5 h / 52 °C
2.1: sulfuric acid; potassium nitrate / 1.5 h / 0 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 4 h / 0 °C
4.1: trichlorophosphate / 1,2-dichloro-ethane / 3 h / 70 °C
View Scheme
(2,2-Dimethoxy-ethyl)-[1-p-tolyl-meth-(Z)-ylidene]-amine
54879-70-8

(2,2-Dimethoxy-ethyl)-[1-p-tolyl-meth-(Z)-ylidene]-amine

1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: chloroformic acid ethyl ester; triethyl phosphite / chloroform / 24 h / 0 - 20 °C
1.2: 0 °C / Reflux
2.1: sulfuric acid; potassium nitrate / 0 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C
4.1: trichlorophosphate / 1,2-dichloro-ethane / Reflux
View Scheme
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

m-aminobenzenesulfonamide
98-18-0

m-aminobenzenesulfonamide

C16H14N4O4S

C16H14N4O4S

Conditions
ConditionsYield
With trifluoroacetic acid In isopropyl alcohol at 20 - 90℃; for 18h; Inert atmosphere;99.4%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

3-(methylsulfonamido)aniline
37045-73-1

3-(methylsulfonamido)aniline

N-(3-((6-methyl-5-nitroisoquinolin-1-yl)amino)phenyl)methanesulfonamide
1446113-45-6

N-(3-((6-methyl-5-nitroisoquinolin-1-yl)amino)phenyl)methanesulfonamide

Conditions
ConditionsYield
In isopropyl alcohol at 120℃; for 1.5h; Sealed tube;99%
In isopropyl alcohol at 120℃; for 1.5h; Sealed tube;99%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

C18H17N3O4

C18H17N3O4

Conditions
ConditionsYield
With trifluoroacetic acid In isopropyl alcohol at 20 - 90℃; for 16h; Inert atmosphere;98.4%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

3-acetylenephenylamine
54060-30-9

3-acetylenephenylamine

C18H13N3O2

C18H13N3O2

Conditions
ConditionsYield
With trifluoroacetic acid In isopropyl alcohol at 20 - 90℃; for 16h; Inert atmosphere;95.4%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

4-chloro-aniline
106-47-8

4-chloro-aniline

N-(4-chlorophenyl)-6-methyl-5-nitroisoquinolin-1-amine
1191460-78-2

N-(4-chlorophenyl)-6-methyl-5-nitroisoquinolin-1-amine

Conditions
ConditionsYield
In isopropyl alcohol at 90℃; Sealed tube;95%
In isopropyl alcohol at 90℃; Sealed tube;95%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

3-trifluoromethylaniline
98-16-8

3-trifluoromethylaniline

6-methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinoline-1-amine
943606-86-8

6-methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinoline-1-amine

Conditions
ConditionsYield
In isopropyl alcohol at 90℃; for 12h;94%
In isopropyl alcohol at 90℃; Sealed tube;94%
In isopropyl alcohol at 180℃; for 0.416667h; Microwave irradiation;79%
In isopropyl alcohol at 180℃; for 0.416667h; Microwave irradiation;79%
In isopropyl alcohol at 180℃; for 0.416667h; microwave;79%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

C17H11ClF3N3O2

C17H11ClF3N3O2

Conditions
ConditionsYield
With trifluoroacetic acid In isopropyl alcohol at 20 - 90℃; for 18h; Inert atmosphere;93.3%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

m-trifluoromethoxyaniline
1535-73-5

m-trifluoromethoxyaniline

C17H12F3N3O3

C17H12F3N3O3

Conditions
ConditionsYield
With trifluoroacetic acid In isopropyl alcohol at 20 - 90℃; for 18h; Inert atmosphere;91.9%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

5-amino-1-chloro-6-methylisoquinoline
1093101-44-0

5-amino-1-chloro-6-methylisoquinoline

Conditions
ConditionsYield
With hydrogen In tetrahydrofuran at 20℃; under 2250.23 Torr; for 18h; chemoselective reaction;90.1%
With hydrogenchloride; iron In ethanol; water for 5h; Reflux;83%
With tin(ll) chloride In ethanol; dichloromethane at 70℃; for 16h;40%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-(6-methyl-5-nitroisoquinolin-1-ylamino)benzonitrile
1093101-45-1

4-(6-methyl-5-nitroisoquinolin-1-ylamino)benzonitrile

Conditions
ConditionsYield
Stage #1: 1-chloro-6-methyl-5-nitroisoquinoline; 4-Aminobenzonitrile In isopropyl alcohol at 22℃;
Stage #2: With trifluoroacetic acid In isopropyl alcohol at 80℃; for 17h;
88%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

6-methyl-5-nitroisoquinolin-1(2H)-one
943606-85-7

6-methyl-5-nitroisoquinolin-1(2H)-one

Conditions
ConditionsYield
With hydrogenchloride; water In tetrahydrofuran Heating / reflux;87%
With hydrogenchloride; water In tetrahydrofuran for 14h; Reflux;87%
With hydrogenchloride In tetrahydrofuran; water for 14h; Heating / reflux;87%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

4-chloro-aniline
106-47-8

4-chloro-aniline

N-(4-chlorophenyl)-6-methyl-5-nitroisoquinolin-1-amine hydrochloride
1191385-24-6

N-(4-chlorophenyl)-6-methyl-5-nitroisoquinolin-1-amine hydrochloride

Conditions
ConditionsYield
In isopropyl alcohol at 170℃; for 0.266667h; Microwave irradiation;84%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

1-methoxy-6-methyl-5-nitroisoquinoline
260049-39-6

1-methoxy-6-methyl-5-nitroisoquinoline

Conditions
ConditionsYield
With sodium methylate In methanol74%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

2,4-difluorophenylamine
367-25-9

2,4-difluorophenylamine

C16H11F2N3O2

C16H11F2N3O2

Conditions
ConditionsYield
With trifluoroacetic acid In isopropyl alcohol at 20 - 90℃; for 16h; Inert atmosphere;73.7%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

tert-butyl 4-(5-amino-2-chlorobenzyl)piperazine-1-carboxylate
769961-14-0

tert-butyl 4-(5-amino-2-chlorobenzyl)piperazine-1-carboxylate

tert-butyl 4-(2-chloro-5-((6-methyl-5-nitroisoquinolin-1-yl)amino)benzyl)piperazine-1-carboxylate
1446113-47-8

tert-butyl 4-(2-chloro-5-((6-methyl-5-nitroisoquinolin-1-yl)amino)benzyl)piperazine-1-carboxylate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 130℃; for 3h; Sealed tube;54%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 130℃; for 3h; Sealed tube;54%
4-chloro-3-((dimethylamino)methyl)aniline

4-chloro-3-((dimethylamino)methyl)aniline

1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

N-(4-chloro-3-((dimethylamino)methyl)phenyl)-6-methyl-5-nitroisoquinolin-1-amine
1446113-42-3

N-(4-chloro-3-((dimethylamino)methyl)phenyl)-6-methyl-5-nitroisoquinolin-1-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 130℃; for 3h;53%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 130℃; for 3h; Sealed tube;53%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

2-amino-4-(trifluoromethyl)pyridine
106447-97-6

2-amino-4-(trifluoromethyl)pyridine

6-methyl-5-nitro-N-(4-(trifluoromethyl)pyridin-2-yl)isoquinolin-1-amine
1446113-36-5

6-methyl-5-nitro-N-(4-(trifluoromethyl)pyridin-2-yl)isoquinolin-1-amine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; Sealed tube;42%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃;42%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

5-tert-butyl-2-methyl-2H-pyrazol-3-ylamine
118430-73-2

5-tert-butyl-2-methyl-2H-pyrazol-3-ylamine

C18H21N5O2

C18H21N5O2

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane; DavePhos In 1,4-dioxane at 150℃; for 0.5h; Microwave irradiation; Sealed tube;32.8%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

(R)-1-(4-chlorophenyl)ethylamine
27298-99-3

(R)-1-(4-chlorophenyl)ethylamine

(R)-N-(1-(4-chlorophenyl)ethyl)-6-methyl-5-nitroisoquinolin-1-amine
1093101-68-8

(R)-N-(1-(4-chlorophenyl)ethyl)-6-methyl-5-nitroisoquinolin-1-amine

Conditions
ConditionsYield
With trifluoroacetic acid In isopropyl alcohol at 140℃; for 1h; microwave;
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

A

5-amino-1-chloro-6-methylisoquinoline
1093101-44-0

5-amino-1-chloro-6-methylisoquinoline

B

5-amino-6-methylisoquinoline
188120-79-8

5-amino-6-methylisoquinoline

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran at 37℃; under 2250.23 - 3000.3 Torr; for 15h;A 84.4 %Chromat.
B 15.6 %Chromat.
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

N1-(4-chloro-3-((dimethylamino)methyl)phenyl)-6-methylisoquinoline-1,5-diamine
1446113-43-4

N1-(4-chloro-3-((dimethylamino)methyl)phenyl)-6-methylisoquinoline-1,5-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / 1,4-dioxane / 3 h / 130 °C
2: iron; hydrogenchloride / water; ethanol / 1 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 3 h / 130 °C / Sealed tube
2: hydrogenchloride; iron / water; ethanol / 1 h / Reflux
View Scheme
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

4-amino-N-(1-((4-chloro-3-((dimethylamino)methyl)phenyl)amino)-6-methylisoquinolin-5-yl)thieno[3,2-d]pyrimidine-7-carboxamide
1446112-11-3

4-amino-N-(1-((4-chloro-3-((dimethylamino)methyl)phenyl)amino)-6-methylisoquinolin-5-yl)thieno[3,2-d]pyrimidine-7-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / 1,4-dioxane / 3 h / 130 °C
2: iron; hydrogenchloride / water; ethanol / 1 h / Reflux
3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h
View Scheme
Multi-step reaction with 3 steps
1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 3 h / 130 °C / Sealed tube
2: hydrogenchloride; iron / water; ethanol / 1 h / Reflux
3: N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide
View Scheme
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

N-(3-((5-amino-6-methylisoquinolin-1-yl)amino)phenyl)methanesulfonamide
1446113-46-7

N-(3-((5-amino-6-methylisoquinolin-1-yl)amino)phenyl)methanesulfonamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: isopropyl alcohol / 1.5 h / 120 °C / Sealed tube
2: iron; hydrogenchloride / water; ethanol / 3 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: isopropyl alcohol / 1.5 h / 120 °C / Sealed tube
2: hydrogenchloride; iron / water; ethanol / 3 h / Reflux
View Scheme
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

4-amino-N-(6-methyl-1-((3-(methylsulfonamido)phenyl)amino)isoquinolin-5-yl)thieno[3,2-d]pyrimidine-7-carboxamide
1446112-26-0

4-amino-N-(6-methyl-1-((3-(methylsulfonamido)phenyl)amino)isoquinolin-5-yl)thieno[3,2-d]pyrimidine-7-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: isopropyl alcohol / 1.5 h / 120 °C / Sealed tube
2: iron; hydrogenchloride / water; ethanol / 3 h / Reflux
3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h
View Scheme
Multi-step reaction with 3 steps
1: isopropyl alcohol / 1.5 h / 120 °C / Sealed tube
2: hydrogenchloride; iron / water; ethanol / 3 h / Reflux
3: N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h
View Scheme
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

tert-butyl 4-(5-((5-amino-6-methylisoquinolin-1-yl)amino)-2-chlorobenzyl)piperazine-1-carboxylate
1446113-48-9

tert-butyl 4-(5-((5-amino-6-methylisoquinolin-1-yl)amino)-2-chlorobenzyl)piperazine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / 1,4-dioxane / 3 h / 130 °C / Sealed tube
2: iron; hydrogenchloride / water; ethanol / 3 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 3 h / 130 °C / Sealed tube
2: hydrogenchloride; iron / water; ethanol / 3 h / Reflux
View Scheme

943606-84-6Downstream Products

943606-84-6Relevant articles and documents

An Efficient Second-Generation Manufacturing Process for the pan-RAF Inhibitor Belvarafenib

Zell, Daniel,Dalziel, Michael E.,Carrera, Diane E.,Stumpf, Andreas,Bachmann, Stephan,Mercado-Marin, Eduardo,Koenig, Stefan G.,Zhang, Haiming,Gosselin, Francis

, p. 2338 - 2350 (2021/09/28)

Herein, the development of a streamlined manufacturing process for the pan-RAF inhibitor belvarafenib (GDC-5573) is reported. The process to belvarafenib features a number of efficient key reactions, including a robust and scalable Pd-catalyzed carbonylation reaction to generate thienopyrimidine 2 and a highly chemoselective Pt/V/C-catalyzed nitro group reduction to access the penultimate intermediate 3. The final amide coupling was accomplished by a mild and safe protocol employing N,N,N′,N′-tetramethylchloroformamidinium hexafluorophosphate as the coupling reagent, which afforded belvarafenib on a multikilogram production scale after recrystallization.

ISOQUINOLINE-5-CARBOXAMIDE DERIVATIVE HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASE

-

, (2015/07/15)

A compound selected from the group consisting of an isoquinoline-5-carboxamide derivative of formula (I), a pharmaceutically acceptable salt, an isomer, a hydrate and a solvate thereof is effective for the prevention or treatment of diseases associated with abnormal cell growth, which are caused by abnormal activation of a protein kinases.

THIENO[3,2-d]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASES

-

, (2013/07/19)

Provided are a thieno[3,2-d]pyrimidine derivative of formula (I) or a pharmaceutically acceptable salt thereof having inhibitory activity for protein kinase, and a pharmaceutical composition comprising same for prevention and treatment of abnormal cell growth diseases

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