Product Name

  • Name

    8-FLUOR-2-{4-[(METHYLAMINO)METHYL]FENYL}-1,3,4,5-TETRAHYDRO-6HAZEPINO[5,4,3-CD]INDOOL-6-ON

  • EINECS 814-445-0
  • CAS No. 283173-50-2
  • Article Data17
  • CAS DataBase
  • Density 1.281 g/cm3
  • Solubility
  • Melting Point
  • Formula C19H18FN3O
  • Boiling Point 625.248 °C at 760 mmHg
  • Molecular Weight 323.37
  • Flash Point 331.938 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 283173-50-2 (8-FLUOR-2-{4-[(METHYLAMINO)METHYL]FENYL}-1,3,4,5-TETRAHYDRO-6HAZEPINO[5,4,3-CD]INDOOL-6-ON)
  • Hazard Symbols
  • Synonyms 6H-Azepino[5,4,3-cd]indol-6-one,8-fluoro-1,3,4,5-tetrahydro-2-[4-[(methylamino)methyl]phenyl]- (9CI);8-Fluoro-2-[4-[(methylamino)methyl]phenyl]-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one;8-fluoro-2-(4-((methylamino)methyl)phenyl)-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one;
  • PSA 56.92000
  • LogP 3.69900

Synthetic route

C19H16FN3O

C19H16FN3O

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Stage #1: C19H16FN3O With sodium tetrahydroborate In ethanol for 1h;
Stage #2: With sodium hydroxide In water at 10℃; for 2h;		90.83%
With palladium 10% on activated carbon; hydrogen for 12h; Reagent/catalyst;84%
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 3 h / 0 - 20 °C / Large scale
1.2: 1 h / Large scale
1.3: 18 h / Large scale
2.1: sodium hydroxide / methanol; water; tetrahydrofuran / 18 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2 h / 0 - 20 °C
1.2: 2 h
2.1: sodium hydroxide / water; methanol / 12 h / 0 - 5 °C
View Scheme
[4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-2-yl)-benzyl]-methyl-carbamic acid methyl ester
880160-69-0

[4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-2-yl)-benzyl]-methyl-carbamic acid methyl ester

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
With hydrogen bromide; acetic acid at 20℃; for 12h;89.7%
Stage #1: [4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-2-yl)-benzyl]-methyl-carbamic acid methyl ester With hydrogen bromide; acetic acid at 20℃; for 46h;
Stage #2: With sodium hydroxide In water at 0 - 35℃; pH=10;		88%
tert-butyl (4-(6-(tert-butyl)-8-fluoro-2-(4-methoxybenzyl)-1-oxo-2,3,4,6-tetrahydro-1H-azepino[5,4,3-cd]indol-5-yl)benzyl)(methyl)carbamate

tert-butyl (4-(6-(tert-butyl)-8-fluoro-2-(4-methoxybenzyl)-1-oxo-2,3,4,6-tetrahydro-1H-azepino[5,4,3-cd]indol-5-yl)benzyl)(methyl)carbamate

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
With trifluoroacetic acid at 100℃; for 24h; Sealed tube;88%
C35H40FN3O4

C35H40FN3O4

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
With diphenylether; trifluoroacetic acid at 100℃; for 24h;88%
C27H24FN3O3

C27H24FN3O3

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In ethanol; ethyl acetate at 20℃; for 2h;87.4%
4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-aza-[5,4,3-cd]indol-2-yl)benzyl(methyl)benzyl amine

4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-aza-[5,4,3-cd]indol-2-yl)benzyl(methyl)benzyl amine

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In tetrahydrofuran; ethanol at 20℃; for 2h;86.8%
8-fluoro-2-((4-methylaminomethyl)phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one hydrochloride
773059-19-1

8-fluoro-2-((4-methylaminomethyl)phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one hydrochloride

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 18h; Large scale;84%
4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd] indol-2-yl)-benzaldehyde
283173-84-2

4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd] indol-2-yl)-benzaldehyde

methylamine
74-89-5

methylamine

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Stage #1: 4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd] indol-2-yl)-benzaldehyde; methylamine In methanol at 20℃; for 2h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 20℃;		66%
4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd] indol-2-yl)-benzaldehyde
283173-84-2

4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd] indol-2-yl)-benzaldehyde

2-phenyl-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one
283172-68-9

2-phenyl-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
With methylamine
4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd] indol-2-yl)-benzaldehyde
283173-84-2

4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd] indol-2-yl)-benzaldehyde

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; sodium cyanoborohydride / methanol; water; tetrahydrofuran; ethanol / Large scale
2: sodium hydroxide / methanol; water; tetrahydrofuran / 18 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 3 steps
1.1: methanol; tetrahydrofuran; ethanol / 2 h / Large scale
2.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 3 h / 0 - 20 °C / Large scale
2.2: 1 h / Large scale
2.3: 18 h / Large scale
3.1: sodium hydroxide / methanol; water; tetrahydrofuran / 18 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 3 steps
1.1: methanol; tetrahydrofuran / 2 h / 0 - 20 °C
2.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2 h / 0 - 20 °C
2.2: 2 h
3.1: sodium hydroxide / water; methanol / 12 h / 0 - 5 °C
View Scheme
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / ethanol / 2 h / 10 °C
2.1: sodium tetrahydroborate / ethanol / 1 h
2.2: 2 h / 10 °C
View Scheme
3-(2-(phthalimido)ethyl)-6-fluoro-1H-indole-4-carboxylic acid methyl ester
1408282-25-6

3-(2-(phthalimido)ethyl)-6-fluoro-1H-indole-4-carboxylic acid methyl ester

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: methylamine / water / 17 h / 20 °C / Large scale
2.1: pyridinium hydrobromide perbromide / tetrahydrofuran; dichloromethane / 1 h / 0 - 5 °C / Large scale
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl acetamide / 2 h / 20 - 95 °C / Large scale
3.2: 9 h / 20 °C / Large scale
4.1: hydrogenchloride; sodium cyanoborohydride / methanol; water; tetrahydrofuran; ethanol / Large scale
5.1: sodium hydroxide / methanol; water; tetrahydrofuran / 18 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 6 steps
1.1: methylamine / water / 17 h / 20 °C / Large scale
2.1: pyridinium hydrobromide perbromide / tetrahydrofuran; dichloromethane / 1 h / 0 - 5 °C / Large scale
3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl acetamide / 2 h / 20 - 95 °C / Large scale
3.2: 9 h / 20 °C / Large scale
4.1: methanol; tetrahydrofuran; ethanol / 2 h / Large scale
5.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 3 h / 0 - 20 °C / Large scale
5.2: 1 h / Large scale
5.3: 18 h / Large scale
6.1: sodium hydroxide / methanol; water; tetrahydrofuran / 18 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 5 steps
1.1: methylamine / water / 24 h / 0 - 20 °C
2.1: pyridinium hydrobromide perbromide; sodium carbonate / dichloromethane; tetrahydrofuran / 1 h / 10 - 20 °C
3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl acetamide / 1 h / 20 - 95 °C / Inert atmosphere
3.2: 2 h / 20 - 98 °C / Inert atmosphere
4.1: tetrahydrofuran; methanol; ethanol / 12 h / 25 - 33 °C
5.1: palladium 10% on activated carbon; hydrogen / 12 h
View Scheme
6-fluoro-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4(13),5,7-tetraen-9-one
1408282-26-7

6-fluoro-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4(13),5,7-tetraen-9-one

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: pyridinium hydrobromide perbromide / tetrahydrofuran; dichloromethane / 1 h / 0 - 5 °C / Large scale
2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl acetamide / 2 h / 20 - 95 °C / Large scale
2.2: 9 h / 20 °C / Large scale
3.1: hydrogenchloride; sodium cyanoborohydride / methanol; water; tetrahydrofuran; ethanol / Large scale
4.1: sodium hydroxide / methanol; water; tetrahydrofuran / 18 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 5 steps
1.1: pyridinium hydrobromide perbromide / tetrahydrofuran; dichloromethane / 1 h / 0 - 5 °C / Large scale
2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl acetamide / 2 h / 20 - 95 °C / Large scale
2.2: 9 h / 20 °C / Large scale
3.1: methanol; tetrahydrofuran; ethanol / 2 h / Large scale
4.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 3 h / 0 - 20 °C / Large scale
4.2: 1 h / Large scale
4.3: 18 h / Large scale
5.1: sodium hydroxide / methanol; water; tetrahydrofuran / 18 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 3 steps
1.1: Pyr·HBr3 / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C
2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 12 h / 90 °C
3.1: methanol / 2 h / 20 °C
3.2: 0 - 20 °C
View Scheme
2-bromo-8-fluoro-1,3,4,5-tetrahydro-6H-pyrrolo[4,3,2-ef][2]benzazepin-6-one
283173-80-8

2-bromo-8-fluoro-1,3,4,5-tetrahydro-6H-pyrrolo[4,3,2-ef][2]benzazepin-6-one

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl acetamide / 2 h / 20 - 95 °C / Large scale
1.2: 9 h / 20 °C / Large scale
2.1: hydrogenchloride; sodium cyanoborohydride / methanol; water; tetrahydrofuran; ethanol / Large scale
3.1: sodium hydroxide / methanol; water; tetrahydrofuran / 18 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 4 steps
1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl acetamide / 2 h / 20 - 95 °C / Large scale
1.2: 9 h / 20 °C / Large scale
2.1: methanol; tetrahydrofuran; ethanol / 2 h / Large scale
3.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 3 h / 0 - 20 °C / Large scale
3.2: 1 h / Large scale
3.3: 18 h / Large scale
4.1: sodium hydroxide / methanol; water; tetrahydrofuran / 18 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 2 steps
1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 12 h / 90 °C
2.1: methanol / 2 h / 20 °C
2.2: 0 - 20 °C
View Scheme
C16H17ClFNO2

C16H17ClFNO2

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: aluminum (III) chloride; chloroacetyl chloride / 2 h / 20 °C
2.1: hydroxylamine hydrochloride; sodium acetate / tetrahydrofuran; methanol; water / 2 h / 50 °C
3.1: thionyl chloride / 1,4-dioxane / 6 h / 70 °C
4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; water / tetrahydrofuran / 24 h / 20 °C
5.1: Pyr·HBr3 / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C
6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 12 h / 90 °C
7.1: methanol / 2 h / 20 °C
7.2: 0 - 20 °C
View Scheme
C16H16FNO2

C16H16FNO2

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydroxylamine hydrochloride; sodium acetate / tetrahydrofuran; methanol; water / 2 h / 50 °C
2.1: thionyl chloride / 1,4-dioxane / 6 h / 70 °C
3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; water / tetrahydrofuran / 24 h / 20 °C
4.1: Pyr·HBr3 / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C
5.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 12 h / 90 °C
6.1: methanol / 2 h / 20 °C
6.2: 0 - 20 °C
View Scheme
6-fluoro-1H-indole
399-51-9

6-fluoro-1H-indole

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: acetic anhydride; acetic acid / 48 h / 50 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C
2.2: 1 h
3.1: thionyl chloride / 1,2-dichloro-ethane / 1 h / 20 °C
4.1: aluminum (III) chloride; chloroacetyl chloride / 2 h / 20 °C
5.1: hydroxylamine hydrochloride; sodium acetate / tetrahydrofuran; methanol; water / 2 h / 50 °C
6.1: thionyl chloride / 1,4-dioxane / 6 h / 70 °C
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; water / tetrahydrofuran / 24 h / 20 °C
8.1: Pyr·HBr3 / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C
9.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 12 h / 90 °C
10.1: methanol / 2 h / 20 °C
10.2: 0 - 20 °C
View Scheme
C16H17FN2O2

C16H17FN2O2

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / 1,4-dioxane / 6 h / 70 °C
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; water / tetrahydrofuran / 24 h / 20 °C
3.1: Pyr·HBr3 / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C
4.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 12 h / 90 °C
5.1: methanol / 2 h / 20 °C
5.2: 0 - 20 °C
View Scheme
C16H17FN2O2

C16H17FN2O2

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; water / tetrahydrofuran / 24 h / 20 °C
2.1: Pyr·HBr3 / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C
3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 12 h / 90 °C
4.1: methanol / 2 h / 20 °C
4.2: 0 - 20 °C
View Scheme
6-Fluoroindole-3-propionic acid
141071-78-5

6-Fluoroindole-3-propionic acid

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C
1.2: 1 h
2.1: thionyl chloride / 1,2-dichloro-ethane / 1 h / 20 °C
3.1: aluminum (III) chloride; chloroacetyl chloride / 2 h / 20 °C
4.1: hydroxylamine hydrochloride; sodium acetate / tetrahydrofuran; methanol; water / 2 h / 50 °C
5.1: thionyl chloride / 1,4-dioxane / 6 h / 70 °C
6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; water / tetrahydrofuran / 24 h / 20 °C
7.1: Pyr·HBr3 / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C
8.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 12 h / 90 °C
9.1: methanol / 2 h / 20 °C
9.2: 0 - 20 °C
View Scheme
C16H18FNO3

C16H18FNO3

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: thionyl chloride / 1,2-dichloro-ethane / 1 h / 20 °C
2.1: aluminum (III) chloride; chloroacetyl chloride / 2 h / 20 °C
3.1: hydroxylamine hydrochloride; sodium acetate / tetrahydrofuran; methanol; water / 2 h / 50 °C
4.1: thionyl chloride / 1,4-dioxane / 6 h / 70 °C
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; water / tetrahydrofuran / 24 h / 20 °C
6.1: Pyr·HBr3 / tetrahydrofuran; dichloromethane / 2 h / 0 - 20 °C
7.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane / 12 h / 90 °C
8.1: methanol / 2 h / 20 °C
8.2: 0 - 20 °C
View Scheme
4-formylphenylboronic acid,
87199-17-5

4-formylphenylboronic acid,

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol / 0 - 20 °C
2: hydrogen / ethanol / 5 h / 40 °C / 3750.38 Torr / Autoclave
3: bis(acetato)bis(triphenylphosphine)palladium(0); sodium carbonate / methanol; water / 4 h / 60 °C / Inert atmosphere
View Scheme
8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one phosphate

8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one phosphate

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 30℃; for 1.5h;
C8H10BNO2

C8H10BNO2

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / ethanol / 5 h / 40 °C / 3750.38 Torr / Autoclave
2: bis(acetato)bis(triphenylphosphine)palladium(0); sodium carbonate / methanol; water / 4 h / 60 °C / Inert atmosphere
View Scheme
2-bromo-8-fluoro-1,3,4,5-tetrahydro-6H-pyrrolo[4,3,2-ef][2]benzazepin-6-one
283173-80-8

2-bromo-8-fluoro-1,3,4,5-tetrahydro-6H-pyrrolo[4,3,2-ef][2]benzazepin-6-one

(4-((methylamino)methyl)phenyl)boronic acid
518336-26-0

(4-((methylamino)methyl)phenyl)boronic acid

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
With bis(acetato)bis(triphenylphosphine)palladium(0); sodium carbonate In methanol; water at 60℃; for 4h; Reagent/catalyst; Inert atmosphere;6.82 g
ADDQNPWRAYLDLLFPTDTLLLDLLWC{[(2R)-1-({[(4-{6-fluoro-9-oxo-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-2-yl}phenyl)methyl](methyl)carbamoyl}oxy)propan-2-yl]sulfanyl}G

ADDQNPWRAYLDLLFPTDTLLLDLLWC{[(2R)-1-({[(4-{6-fluoro-9-oxo-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-2-yl}phenyl)methyl](methyl)carbamoyl}oxy)propan-2-yl]sulfanyl}G

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
With GLUTATHIONE In aq. buffer at 37℃;
2-(4-(4-((methylamino)methyl)phenyl)but-3-yn-1-yl)isoindoline-1,3-dione

2-(4-(4-((methylamino)methyl)phenyl)but-3-yn-1-yl)isoindoline-1,3-dione

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triethylamine / dichloromethane / 18.22 h / 0 - 20 °C
2: trifluoroacetic acid; trifluorormethanesulfonic acid / water / 18 h / 20 °C
3: boron trifluoride diethyl etherate; acetic acid / 18 h / 90 °C / Inert atmosphere
4: hydrazine / ethanol; tetrahydrofuran / 9 h / 110 °C
5: 5%-palladium/activated carbon; hydrogen; hydrogenchloride / water; methanol / 18 h / 20 °C
View Scheme
N-(4-(4-(1,3-dioxoisoindolin-2-yl)but-1-yn-1-yl)benzyl)-2,2,2-trifluoro-N-methylacetamide

N-(4-(4-(1,3-dioxoisoindolin-2-yl)but-1-yn-1-yl)benzyl)-2,2,2-trifluoro-N-methylacetamide

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: trifluoroacetic acid; trifluorormethanesulfonic acid / water / 18 h / 20 °C
2: boron trifluoride diethyl etherate; acetic acid / 18 h / 90 °C / Inert atmosphere
3: hydrazine / ethanol; tetrahydrofuran / 9 h / 110 °C
4: 5%-palladium/activated carbon; hydrogen; hydrogenchloride / water; methanol / 18 h / 20 °C
View Scheme
N-(4-(4-(1,3-dioxoisoindolin-2-yl)butanoyl)benzyl)-2,2,2-trifluoro-N-methylacetamide

N-(4-(4-(1,3-dioxoisoindolin-2-yl)butanoyl)benzyl)-2,2,2-trifluoro-N-methylacetamide

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: boron trifluoride diethyl etherate; acetic acid / 18 h / 90 °C / Inert atmosphere
2: hydrazine / ethanol; tetrahydrofuran / 9 h / 110 °C
3: 5%-palladium/activated carbon; hydrogen; hydrogenchloride / water; methanol / 18 h / 20 °C
View Scheme
9-bromo-8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-pyrrolo[4,3,2-ef][2]benzazepin-6-one

9-bromo-8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-pyrrolo[4,3,2-ef][2]benzazepin-6-one

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
With hydrogenchloride; 5%-palladium/activated carbon; hydrogen In methanol; water at 20℃; for 18h;734 mg
N-methyl-4-bromobenzylamine
699-03-6

N-methyl-4-bromobenzylamine

Rucaparib
283173-50-2

Rucaparib

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: copper(l) iodide; caesium carbonate / 1,4-dioxane / 1.25 h / Inert atmosphere
1.2: 19 h / 80 °C / Inert atmosphere
2.1: triethylamine / dichloromethane / 18.22 h / 0 - 20 °C
3.1: trifluoroacetic acid; trifluorormethanesulfonic acid / water / 18 h / 20 °C
4.1: boron trifluoride diethyl etherate; acetic acid / 18 h / 90 °C / Inert atmosphere
5.1: hydrazine / ethanol; tetrahydrofuran / 9 h / 110 °C
6.1: 5%-palladium/activated carbon; hydrogen; hydrogenchloride / water; methanol / 18 h / 20 °C
View Scheme
Rucaparib
283173-50-2

Rucaparib

methanesulfonic acid
75-75-2

methanesulfonic acid

8-fluoro-2-(4-methylaminomethylphenyl)-1,3,4,5-tetrahydroazepino[5,4,3-cd]indol-6-one mesylate
773059-20-4

8-fluoro-2-(4-methylaminomethylphenyl)-1,3,4,5-tetrahydroazepino[5,4,3-cd]indol-6-one mesylate

Conditions
ConditionsYield
In methanol97%
In tetrahydrofuran; acetone at 50℃; Solvent;
Rucaparib
283173-50-2

Rucaparib

maleic acid
110-16-7

maleic acid

8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one maleate salt

8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one maleate salt

Conditions
ConditionsYield
In isopropyl alcohol Product distribution / selectivity;97%
Rucaparib
283173-50-2

Rucaparib

[(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid
76-26-6, 3144-16-9, 5872-08-2, 35963-20-3

[(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid

8-fluoro-2-((4-methylaminomethyl)phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one (S)-camphorsulfonate

8-fluoro-2-((4-methylaminomethyl)phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one (S)-camphorsulfonate

Conditions
ConditionsYield
In water; isopropyl alcohol at 70℃; for 1h;95%
In methanol; water at 0 - 40℃; for 29h; Reflux;81%
Rucaparib
283173-50-2

Rucaparib

17-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)-3,6,9,12,15-pentaoxaheptadecanal

17-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)amino)-3,6,9,12,15-pentaoxaheptadecanal

C44H51FN6O10

C44H51FN6O10

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In dichloromethane at 0 - 23℃; for 2h;90%
Rucaparib
283173-50-2

Rucaparib

(1S)-10-camphorsulfonic acid
3144-16-9

(1S)-10-camphorsulfonic acid

8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid salt

8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid salt

Conditions
ConditionsYield
In methanol at 60 - 65℃; for 0.5h;89.86%
In tetrahydrofuran; water for 0.833333h; Product distribution / selectivity; Reflux;
for 2.5h;
In 1,4-dioxane; water at 30℃; for 12h; Time;
Rucaparib
283173-50-2

Rucaparib

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

C24H26FN3O3

C24H26FN3O3

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; for 0.5h;89%
Rucaparib
283173-50-2

Rucaparib

5-hexynal
29329-03-1

5-hexynal

C25H26FN3O

C25H26FN3O

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In dichloromethane at 23℃; for 1h; Inert atmosphere;74%
Rucaparib
283173-50-2

Rucaparib

methyl 4-formylbutanoate
6026-86-4

methyl 4-formylbutanoate

C24H26FN3O3

C24H26FN3O3

Conditions
ConditionsYield
Stage #1: Rucaparib; methyl 4-formylbutanoate With sodium tris(acetoxy)borohydride In dichloromethane at 23℃; for 1h; Inert atmosphere;
Stage #2: With water; lithium hydroxide In tetrahydrofuran at 23℃; for 2h;		54%
Rucaparib
283173-50-2

Rucaparib

Trimethylboroxine
823-96-1

Trimethylboroxine

C20H20FN3O

C20H20FN3O

Conditions
ConditionsYield
With pentamethylcyclopentadienyl(benzene)cobalt(III) hexafluorophosphate; potassium carbonate; silver carbonate In 2-methyltetrahydrofuran at 100℃; for 16h; Inert atmosphere; Sealed tube;39%
methanol
67-56-1

methanol

Rucaparib
283173-50-2

Rucaparib

phosphate salt of 8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one

phosphate salt of 8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one

Conditions
ConditionsYield
Stage #1: methanol; Rucaparib for 0.166667h;
Stage #2: With phosphoric acid In methanol at 20℃; for 0.5h;
Rucaparib
283173-50-2

Rucaparib

camphor-10-sulfonic acid
76-26-6, 3144-16-9, 5872-08-2, 35963-20-3

camphor-10-sulfonic acid

A

8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid salt

8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid salt

B

8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid salt

8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid salt

Conditions
ConditionsYield
In water; isopropyl alcohol at 70℃; for 0.166667h; Product distribution / selectivity;
...Expand
Rucaparib
283173-50-2

Rucaparib

camphor-10-sulfonic acid
76-26-6, 3144-16-9, 5872-08-2, 35963-20-3

camphor-10-sulfonic acid

CO-338

CO-338

Conditions
ConditionsYield
In water; isopropyl alcohol at 70℃; for 0.166667h;
Rucaparib
283173-50-2

Rucaparib

(R)-10-camphorsulfonic acid
35963-20-3

(R)-10-camphorsulfonic acid

8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid salt

8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid salt

Conditions
ConditionsYield
In water; isopropyl alcohol at 70℃; for 0.166667h;
In ethanol at 75 - 85℃; for 3h; Solvent; Temperature;0.25 g
Rucaparib
283173-50-2

Rucaparib

C27H38ClN6O4Pt(1+)*NO3(1-)

C27H38ClN6O4Pt(1+)*NO3(1-)

C46H54ClFN9O4Pt(1+)*NO3(1-)

C46H54ClFN9O4Pt(1+)*NO3(1-)

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;
Rucaparib
283173-50-2

Rucaparib

C31H40ClN6O4Pt(1+)*NO3(1-)

C31H40ClN6O4Pt(1+)*NO3(1-)

C50H56ClFN9O4Pt(1+)*NO3(1-)

C50H56ClFN9O4Pt(1+)*NO3(1-)

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;

8-Fluoro-1,3,4,5-tetrahydro-2-[4-[(methylamino)methyl]phenyl]-6H-pyrrolo[4,3,2-ef][2]benzazepin-6-one Specification

The CAS register number of 6H-Pyrrolo[4,3,2-ef][2]benzazepin-6-one,8-fluoro-1,3,4,5-tetrahydro-2-[4-[(methylamino)methyl]phenyl]- is 283173-50-2. It also can be called as 8-fluoro-2-(4-((methylamino)methyl)phenyl)-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one and the systematic name about this chemical is 8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one. The molecular formula about this chemical is C19H18FN3O and the molecular weight is 323.369823.

Physical properties about 6H-Pyrrolo[4,3,2-ef][2]benzazepin-6-one,8-fluoro-1,3,4,5-tetrahydro-2-[4-[(methylamino)methyl]phenyl]- are: (1)ACD/LogP: 3.80; (2)ACD/LogD (pH 7.4): 1; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 4; (7)#H bond acceptors: 4; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 56.92 Å2; (11)Index of Refraction: 1.649; (12)Molar Refractivity: 91.911 cm3; (13)Molar Volume: 252.359 cm3; (14)Polarizability: 36.437x10-24cm3; (15)Surface Tension: 52.168 dyne/cm; (16)Density: 1.281 g/cm3; (17)Flash Point: 331.938 °C; (18)Enthalpy of Vaporization: 92.573 kJ/mol; (19)Boiling Point: 625.248 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: Fc4cc2c1c(nc(c1CCNC2=O)c3ccc(cc3)CNC)c4
(2)InChI: InChI=1/C19H18FN3O/c1-21-10-11-2-4-12(5-3-11)18-14-6-7-22-19(24)15-8-13(20)9-16(23-18)17(14)15/h2-5,8-9,21,23H,6-7,10H2,1H3,(H,22,24)
(3)InChIKey: HMABYWSNWIZPAG-UHFFFAOYAU
(4)Std. InChI: InChI=1S/C19H18FN3O/c1-21-10-11-2-4-12(5-3-11)18-14-6-7-22-19(24)15-8-13(20)9-16(23-18)17(14)15/h2-5,8-9,21,23H,6-7,10H2,1H3,(H,22,24)
(5)Std. InChIKey: HMABYWSNWIZPAG-UHFFFAOYSA-N

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View