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873055-55-1

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873055-55-1 Usage

General Description

2,4-Di-tert-butyl-5-nitrophenyl methyl carbonate is a chemical compound typically utilized in the field of chemistry and laboratory research. This chemical, noteworthy for its complex structure, belongs to the organonitrogen compound family characterized by their containing nitrogen atom. It continues to be the subject of intense scientific studies due to its potential applications. However, like many nitro compounds, this substance may pose certain health and environmental risks upon improper handling, demanding utmost care in its use, storage, and disposal. Further details about the compound, including its specific properties or functions, are highly technical and may require a specialized background in chemistry to fully understand.n

Check Digit Verification of cas no

The CAS Registry Mumber 873055-55-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,7,3,0,5 and 5 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 873055-55:
(8*8)+(7*7)+(6*3)+(5*0)+(4*5)+(3*5)+(2*5)+(1*5)=181
181 % 10 = 1
So 873055-55-1 is a valid CAS Registry Number.
InChI:InChI=1S/C16H23NO5/c1-15(2,3)10-8-11(16(4,5)6)13(22-14(18)21-7)9-12(10)17(19)20/h8-9H,1-7H3

873055-55-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,4-Di-tert-butyl-5-nitrophenyl methyl carbonate

1.2 Other means of identification

Product number -
Other names (2,4-ditert-butyl-5-nitrophenyl) methyl carbonate

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:873055-55-1 SDS

873055-55-1Synthetic route

carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester
873055-54-0

carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

Conditions
ConditionsYield
With aluminum (III) chloride; sodium nitrate In dichloromethane at -21 - -12℃; Temperature; Large scale;83.6%
With sulfuric acid; nitric acid at 0 - 5℃; for 2.5h;40%
Stage #1: carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester With sulfuric acid In dichloromethane at -5 - 0℃;
Stage #2: With nitric acid In dichloromethane at -5 - 0℃; Product distribution / selectivity;
carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester
873055-54-0

carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester

A

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

B

carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester
873055-56-2

carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 0 - 50℃; for 2h;
With sulfuric acid; nitric acid at 20 - 50℃; Cooling with ice;
With nitric acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sulfuric acid
carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester

carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester

A

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

B

carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester
873055-56-2

carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 0 - 50℃; for 2h;
2,4-di-tert-Butylphenol
96-76-4

2,4-di-tert-Butylphenol

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / diethyl ether / 0 - 20 °C
2: nitric acid; sulfuric acid / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / diethyl ether / 2 h / 0 - 20 °C
2.1: sulfuric acid / dichloromethane / 4.5 h / -5 - 0 °C
2.2: -5 - 5 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / diethyl ether / 0 - 20 °C
2: sulfuric acid; nitric acid / 1 h / 0 - 20 °C
View Scheme
carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester
873055-54-0

carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester

4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran
96042-30-7

4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

Conditions
ConditionsYield
With sulfuric acid; nitric acid; sodium sulfate In hexane; water
With nitric acid; sodium sulfate
2,4-di-tert-Butylphenol
96-76-4

2,4-di-tert-Butylphenol

A

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

B

carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester
873055-56-2

carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; triethylamine / dichloromethane / 16 h / 0 - 25 °C
2: sulfuric acid; nitric acid / 2 h / 25 °C / Cooling
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / diethyl ether
2: nitric acid / (2S)-N-methyl-1-phenylpropan-2-amine hydrate; sulfuric acid
View Scheme
Multi-step reaction with 2 steps
1: triethylamine; dmap / dichloromethane / 0 - 20 °C
2: nitric acid; sulfuric acid / 2 h / Cooling with ice
View Scheme
2,4-di-tert-Butylphenol
96-76-4

2,4-di-tert-Butylphenol

methyl chloroformate
79-22-1

methyl chloroformate

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

Conditions
ConditionsYield
Stage #1: 2,4-di-tert-Butylphenol; methyl chloroformate With dmap; triethylamine In dichloromethane at 0 - 5℃; for 2h;
Stage #2: With sulfuric acid; nitric acid at 0 - 5℃; for 1.5h;
4.0 g
2,4-di-tert-butyl-5-nitro-phenol
873055-57-3

2,4-di-tert-butyl-5-nitro-phenol

methyl chloroformate
79-22-1

methyl chloroformate

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 30℃;36.6 g
carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester
873055-54-0

carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester

A

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

B

carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester
873055-56-2

carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester

C

C12H15NO5

C12H15NO5

Conditions
ConditionsYield
With sulfuric acid; nitric acid at -5 - 0℃; for 4h; Reagent/catalyst; Temperature;
carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester
873055-54-0

carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester

A

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

B

C12H15NO5

C12H15NO5

Conditions
ConditionsYield
With aluminum (III) chloride; chloro-trimethyl-silane; potassium nitrate In dichloromethane at 20℃; Temperature;
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

2,4-di-tert-butyl-5-nitro-phenol
873055-57-3

2,4-di-tert-butyl-5-nitro-phenol

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 20℃; for 5h;98%
With potassium hydroxide In methanol
Stage #1: carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester With potassium hydroxide In methanol at 25℃; for 2h;
Stage #2: With hydrogenchloride In methanol; water pH=2 - 3;
1.31 g
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester
873055-56-2

carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester

A

2,4-di-tert-butyl-5-nitro-phenol
873055-57-3

2,4-di-tert-butyl-5-nitro-phenol

B

2,4-di-tert-butyl-6-nitrophenol
20039-94-5

2,4-di-tert-butyl-6-nitrophenol

Conditions
ConditionsYield
With hydrogenchloride; KOH In methanolA 29%
B n/a
Stage #1: carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester; carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester With potassium hydroxide In methanol at 20℃; for 2h;
Stage #2: With hydrogenchloride In methanol; water pH=2 - 3;
Stage #1: carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester; carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester With methanol; potassium hydroxide at 20℃; for 2h;
Stage #2: With hydrogenchloride In water pH=2 - 3;
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

5-amino-2,4-di-tert-butylphenyl methyl carbonate
1182822-31-6

5-amino-2,4-di-tert-butylphenyl methyl carbonate

Conditions
ConditionsYield
With palladium 10% on activated carbon; ammonium formate In ethanol for 2h; Reflux;29%
With hydrogen; 5% Pd(II)/C(eggshell) In methanol at 25℃; under 1500.15 Torr; Inert atmosphere;
With hydrogen; 5%-palladium/activated carbon In methanol at 20 - 30℃; under 1500.15 Torr; Inert atmosphere;
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

ivacaftor
873054-44-5

ivacaftor

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogen / 5%-palladium/activated carbon / methanol / 20 - 30 °C / 1500.15 Torr / Inert atmosphere
2.1: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / 2-methyltetrahydrofuran / 8 h / 47.5 °C
3.1: sodium methylate / 2-methyltetrahydrofuran; methanol / 1 h / 25 °C
3.3: 78 °C
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; 5%-palladium/activated carbon / methanol / 25 °C / 1500.15 Torr / Inert atmosphere
2: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / 2-methyltetrahydrofuran / 8 h / 47.5 °C
3: sodium methylate / methanol; 2-methyltetrahydrofuran / 1 h
View Scheme
Multi-step reaction with 3 steps
1: 5%-palladium/activated carbon; hydrogen / methanol / 25 °C / 1500.15 Torr
2: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / 2-methyltetrahydrofuran / 8 h / 47.5 °C
3: sodium methylate; methanol / 2-methyltetrahydrofuran / 1 h
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

2,4-di-tert-butyl-5-(4-oxo-1,4-dihydroquinoline-3-carboxamido)phenyl methyl carbonate
1246213-45-5

2,4-di-tert-butyl-5-(4-oxo-1,4-dihydroquinoline-3-carboxamido)phenyl methyl carbonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / 5%-palladium/activated carbon / methanol / 20 - 30 °C / 1500.15 Torr / Inert atmosphere
2: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / 2-methyltetrahydrofuran / 8 h / 47.5 °C
View Scheme
Multi-step reaction with 2 steps
1: hydrogen; 5%-palladium/activated carbon / methanol / 25 °C / 1500.15 Torr / Inert atmosphere
2: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / 2-methyltetrahydrofuran / 8 h / 47.5 °C
View Scheme
Multi-step reaction with 2 steps
1: 5%-palladium/activated carbon; hydrogen / methanol / 25 °C / 1500.15 Torr
2: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / 2-methyltetrahydrofuran / 8 h / 47.5 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

5-amino-2,4-di-tert-butyl-phenol
873055-58-4

5-amino-2,4-di-tert-butyl-phenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; KOH / methanol
2: ammonium formate / ethanol
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide / methanol
2: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 25 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium hydroxide / methanol / 2 h / 25 °C
1.2: pH 2 - 3
2.1: ammonium formate; 5%-palladium/activated carbon / ethanol / 2 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: methanol; potassium hydroxide / 2 h / 20 °C
1.2: pH 2 - 3
2.1: ammonium formate / 5% palladium over charcoal / ethanol / 2 h / Heating / reflux
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

C27H32N2O5

C27H32N2O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / Reflux
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

C28H34N2O5

C28H34N2O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / Reflux
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

C27H32N2O6

C27H32N2O6

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / Reflux
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

C26H29FN2O5

C26H29FN2O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / Reflux
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

C30H38N2O5

C30H38N2O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / Reflux
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

C27H29F3N2O5

C27H29F3N2O5

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / Reflux
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide
1236060-10-8

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / Reflux
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C
3: potassium hydroxide / methanol / 2 h / 20 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-ethyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / Reflux
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C
3: potassium hydroxide / methanol / 2 h / 20 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide
1236058-06-2

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / Reflux
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C
3: potassium hydroxide / methanol / 2 h / 20 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide
873051-19-5

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / Reflux
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C
3: potassium hydroxide / methanol / 2 h / 20 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

6-(tert-butyl)-N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

6-(tert-butyl)-N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / Reflux
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C
3: potassium hydroxide / methanol / 2 h / 20 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-6-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxamide
1236058-25-5

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-6-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium formate; palladium 10% on activated carbon / ethanol / 2 h / Reflux
2: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C
3: potassium hydroxide / methanol / 2 h / 20 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

2,4-di-tert-butyl-5-(3-(2-fluorophenyl)-3-oxopropanamido)phenyl methyl carbonate

2,4-di-tert-butyl-5-(3-(2-fluorophenyl)-3-oxopropanamido)phenyl methyl carbonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iron; ammonium chloride / ethanol / 3 h / Reflux
2: ethyl acetate / 6 h / 25 - 60 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

2,4-di-tert-butyl-5-(3-ethoxy-2-(2-fluorobenzoyl)acrylamido)phenyl methyl carbonate

2,4-di-tert-butyl-5-(3-ethoxy-2-(2-fluorobenzoyl)acrylamido)phenyl methyl carbonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: iron; ammonium chloride / ethanol / 3 h / Reflux
2: pyridine / dichloromethane / 0 - 35 °C
3: triethylamine / toluene / 5 h / 25 - 55 °C
View Scheme
Multi-step reaction with 3 steps
1: iron; ammonium chloride / ethanol / 3 h / Reflux
2: ethyl acetate / 6 h / 25 - 60 °C
3: acetic anhydride; zinc(II) chloride / 6 h / 25 - 35 °C
View Scheme
carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester
873055-55-1

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

5-([(E)-3-ethoxyprop-2-enoyl]amino)-2,4-di-tert-butylphenyl methyl carbonate

5-([(E)-3-ethoxyprop-2-enoyl]amino)-2,4-di-tert-butylphenyl methyl carbonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iron; ammonium chloride / ethanol / 3 h / Reflux
2: pyridine / dichloromethane / 0 - 35 °C
View Scheme

873055-55-1Relevant articles and documents

Pharmaceutical compositions for the treatment of cystic fibrosis transmembrane conductance regulator mediated diseases

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, (2021/04/21)

The present invention features compositions comprising a plurality of therapeutic agents wherein the presence of one therapeutic agent enhances the properties of at least one other therapeutic agent. In one embodiment, the therapeutic agents are cystic fibrosis transmembrane conductance regulators (CFTR) such as a CFTR corrector or CFTR potentiator for the treatment of CFTR mediated diseases such as cystic fibrosis. Methods and kits thereof are also disclosed.

Utilizing o-Quinone Methide Chemistry: Synthesis of d9-Ivacaftor

Lewandowski, Bérénice L.,Looker, Adam R.,Roeper, Stefanie,Ryan, Michael P.,Wilde, Nathan,Ye, Zhifeng

, (2020/01/22)

Lead time and cost are important factors for any pharmaceutical API. However, these issues become even more important when the drug substance contains an isotope such as deuterium, which has a natural abundance of only ~0.016% of all hydrogen. Fewer suppliers and logistical barriers both play a role in driving up the cost. These factors can challenge the supply route used to manufacture d9-ivacaftor (17), requiring investigation into alternative routes. By adapting the work from Pettus et al., a synthetic approach utilizing a transient o-quinone methide allowed access to the deuterium-labeled o-tert-butylphenol moiety. This was developed and proven on pilot scale to significantly reduce the number of deuterated reagents used, leading to an overall reduction in cost by a factor of 10, while also providing the substantial benefit of applying prior process knowledge from the parent, nonisotopically enriched API ivacaftor (7).

METHODS OF TREATMENT FOR CYSTIC FIBROSIS

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Paragraph 00230, (2020/12/11)

This application describes methods of treating cystic fibrosis comprising administering Compound I:, a pharmaceutically acceptable salt thereof, or a pharmaceutical composition comprising any of the foregoing.

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