Product Name

  • Name

    Niraparib

  • EINECS
  • CAS No. 1038915-60-4
  • Article Data14
  • CAS DataBase
  • Density 1.343 g/cm3
  • Solubility
  • Melting Point
  • Formula C19H20N4O
  • Boiling Point 463.619 °C at 760 mmHg
  • Molecular Weight 320.394
  • Flash Point 234.188 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 1038915-60-4 (Niraparib)
  • Hazard Symbols
  • Synonyms (S)-2-(4-(Piperidin-3-yl)phenyl)-2H-indazole-7-carboxamide
  • PSA 72.94000
  • LogP 3.62050

Synthetic route

C27H36N4O2S

C27H36N4O2S

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 5,5-dimethyl-1,3-cyclohexadiene at 40℃; for 3h;95%
C19H20N4O*C11H13NO4

C19H20N4O*C11H13NO4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
With sodium hydroxide In water; ethyl acetate at 20℃;94.2%
formaldehyd
50-00-0

formaldehyd

(S)-2-{[4-(piperidin-3-yl)phenyl]azo}benzamide

(S)-2-{[4-(piperidin-3-yl)phenyl]azo}benzamide

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; cobalt(III) acetylacetonate In 1,4-dioxane at 100℃; for 0.333333h; Temperature; Reagent/catalyst; Solvent; Microwave irradiation;93%
2-[4-(3-piperidinyl)phenyl]-2H-indazole-7-carboxamide

2-[4-(3-piperidinyl)phenyl]-2H-indazole-7-carboxamide

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
With N-Ac-Leu In methanol at 70℃; for 1h;91.2%
2-[4-((3S)-3-piperidinyl)phenyl]-2H-indazole-7-carboxamide p-toluenesulfonic acid salt
1038915-73-9

2-[4-((3S)-3-piperidinyl)phenyl]-2H-indazole-7-carboxamide p-toluenesulfonic acid salt

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
With sodium hydroxide In 2-methyltetrahydrofuran at 20℃; for 0.5h;75.9%
With sodium hydroxide In 2-methyltetrahydrofuran; water at 20℃; for 0.5h;75.9%
racemic 3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidinium chloride
1038915-56-8

racemic 3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidinium chloride

A

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

B

2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide
1038915-58-0

2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide

Conditions
ConditionsYield
With diethylamine In isopropyl alcohol at 35℃; under 75007.5 Torr; Purification / work up; Resolution of racemate;
With carbon dioxide Resolution of racemate; Supercritical conditions; optical yield given as %ee;
tert-butyl 3-[4-({[3-(methoxycarbonyl)-2-nitrophenyl]methylene}amino)phenyl]piperidine-1-carboxylate
1038915-99-9

tert-butyl 3-[4-({[3-(methoxycarbonyl)-2-nitrophenyl]methylene}amino)phenyl]piperidine-1-carboxylate

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethyl phosphite / 24 h / 92 °C
2: formamide; sodium methylate / N,N-dimethyl-formamide / 3.5 h / 0 - 40 °C
3: trifluoroacetic acid / dichloromethane / 20 h
4: N-Ac-Leu / methanol / 1 h / 70 °C
View Scheme
methyl 2-{4-[1-(tert-butoxycarbonyl)piperidin-3-yl]phenyl}-2H-indazole-7-carboxylate
1038915-90-0

methyl 2-{4-[1-(tert-butoxycarbonyl)piperidin-3-yl]phenyl}-2H-indazole-7-carboxylate

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: formamide; sodium methylate / N,N-dimethyl-formamide / 3.5 h / 0 - 40 °C
2: trifluoroacetic acid / dichloromethane / 20 h
3: N-Ac-Leu / methanol / 1 h / 70 °C
View Scheme
Multi-step reaction with 4 steps
1: sodium methylate / N,N-dimethyl-formamide / 3.5 h / 40 °C
2: trifluorormethanesulfonic acid / dichloromethane
3: ethanol / 0.5 h / Reflux
4: sodium hydroxide / water; ethyl acetate / 20 °C
View Scheme
3-methyl-2-nitrobenzoic acid
5437-38-7

3-methyl-2-nitrobenzoic acid

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: sulfuric acid / 58 °C
2: manganese(IV) oxide; nitric acid / 40 °C
3: sodium hydrogencarbonate; acetic acid / 2 h / 40 °C
4: triethyl phosphite / 24 h / 92 °C
5: formamide; sodium methylate / N,N-dimethyl-formamide / 3.5 h / 0 - 40 °C
6: trifluoroacetic acid / dichloromethane / 20 h
7: N-Ac-Leu / methanol / 1 h / 70 °C
View Scheme
methyl 3-methyl-2-nitrobenzoate
5471-82-9

methyl 3-methyl-2-nitrobenzoate

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: manganese(IV) oxide; nitric acid / 40 °C
2: sodium hydrogencarbonate; acetic acid / 2 h / 40 °C
3: triethyl phosphite / 24 h / 92 °C
4: formamide; sodium methylate / N,N-dimethyl-formamide / 3.5 h / 0 - 40 °C
5: trifluoroacetic acid / dichloromethane / 20 h
6: N-Ac-Leu / methanol / 1 h / 70 °C
View Scheme
Multi-step reaction with 5 steps
1.1: N,N-dimethyl-formamide / 18 h / 130 °C
2.1: sodium periodate / N,N-dimethyl-formamide / 3.5 h / 20 °C
3.1: hexane / 18 h / Reflux
4.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
5.1: ammonium bicarbonate / methanol / 12 h / 100 °C
5.2: 3 h / 20 °C / pH Ca. 3
View Scheme
Multi-step reaction with 5 steps
1.1: N,N-dimethyl-formamide / 18 h / 130 °C
2.1: sodium periodate / N,N-dimethyl-formamide / 3.5 h / 20 °C
3.1: hexane / 18 h / Reflux
4.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
5.1: ammonium bicarbonate / methanol / 12 h / 100 °C
5.2: 3 h / 20 °C / pH Ca.3
View Scheme
3-formyl-2-nitrobenzoic acid methyl ester
138229-59-1

3-formyl-2-nitrobenzoic acid methyl ester

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium hydrogencarbonate; acetic acid / 2 h / 40 °C
2: triethyl phosphite / 24 h / 92 °C
3: formamide; sodium methylate / N,N-dimethyl-formamide / 3.5 h / 0 - 40 °C
4: trifluoroacetic acid / dichloromethane / 20 h
5: N-Ac-Leu / methanol / 1 h / 70 °C
View Scheme
Multi-step reaction with 3 steps
1.1: hexane / 18 h / Reflux
2.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
3.1: ammonium bicarbonate / methanol / 12 h / 100 °C
3.2: 3 h / 20 °C / pH Ca. 3
View Scheme
Multi-step reaction with 3 steps
1.1: hexane / 18 h / Reflux
2.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
3.1: ammonium bicarbonate / methanol / 12 h / 100 °C
3.2: 3 h / 20 °C / pH Ca.3
View Scheme
β-(dimethylamino)-3-carbomethoxy-2-nitrostyrene
68109-89-7, 93247-79-1

β-(dimethylamino)-3-carbomethoxy-2-nitrostyrene

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium periodate / N,N-dimethyl-formamide / 3.5 h / 20 °C
2.1: hexane / 18 h / Reflux
3.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
4.1: ammonium bicarbonate / methanol / 12 h / 100 °C
4.2: 3 h / 20 °C / pH Ca. 3
View Scheme
Multi-step reaction with 4 steps
1.1: sodium periodate / N,N-dimethyl-formamide / 3.5 h / 20 °C
2.1: hexane / 18 h / Reflux
3.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
4.1: ammonium bicarbonate / methanol / 12 h / 100 °C
4.2: 3 h / 20 °C / pH Ca.3
View Scheme
18-(nitrobenzylideneamino)phenylpiperidine-1-carboxylate
1312106-32-3

18-(nitrobenzylideneamino)phenylpiperidine-1-carboxylate

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
2.1: ammonium bicarbonate / methanol / 12 h / 100 °C
2.2: 3 h / 20 °C / pH Ca. 3
View Scheme
2-[4-((3S)-(tertbutoxycarbonyl)piperidin-3-yl)phenyl]-2H-indazole-7-carboxylic acid methyl ester
1196713-67-3

2-[4-((3S)-(tertbutoxycarbonyl)piperidin-3-yl)phenyl]-2H-indazole-7-carboxylic acid methyl ester

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Stage #1: 2-[4-((3S)-(tertbutoxycarbonyl)piperidin-3-yl)phenyl]-2H-indazole-7-carboxylic acid methyl ester With ammonium bicarbonate In methanol at 100℃; for 12h;
Stage #2: With hydrogenchloride In methanol; water at 20℃; for 3h; pH=Ca. 3;		8.2 g
Stage #1: 2-[4-((3S)-(tertbutoxycarbonyl)piperidin-3-yl)phenyl]-2H-indazole-7-carboxylic acid methyl ester With ammonium bicarbonate In methanol at 100℃; for 12h;
Stage #2: With hydrogenchloride In water at 20℃; for 3h; pH=Ca.3;		8.2 g
3-(4'-nitrophenyl)pyridine
4282-46-6

3-(4'-nitrophenyl)pyridine

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 10 h / 110 °C
2.1: sodium tetrahydroborate; methanol / 8.5 h / 3 - 20 °C
2.2: 24 h / 9120.61 Torr / Autoclave
3.1: L-Tartaric acid / acetonitrile / 10 °C / Reflux
4.1: sodium hydroxide; triethylamine; dmap / dichloromethane / 8 h / 20 °C
5.1: hexane / 18 h / Reflux
6.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
7.1: ammonium bicarbonate / methanol / 12 h / 100 °C
7.2: 3 h / 20 °C / pH Ca. 3
View Scheme
1-benzyl-3-(4-nitrophenyl)pyridinium bromide

1-benzyl-3-(4-nitrophenyl)pyridinium bromide

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium tetrahydroborate; methanol / 8.5 h / 3 - 20 °C
1.2: 24 h / 9120.61 Torr / Autoclave
2.1: L-Tartaric acid / acetonitrile / 10 °C / Reflux
3.1: sodium hydroxide; triethylamine; dmap / dichloromethane / 8 h / 20 °C
4.1: hexane / 18 h / Reflux
5.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
6.1: ammonium bicarbonate / methanol / 12 h / 100 °C
6.2: 3 h / 20 °C / pH Ca. 3
View Scheme
(3S)-3-(4-aminophenyl)piperidine
1196713-21-9

(3S)-3-(4-aminophenyl)piperidine

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide; triethylamine; dmap / dichloromethane / 8 h / 20 °C
2.1: hexane / 18 h / Reflux
3.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
4.1: ammonium bicarbonate / methanol / 12 h / 100 °C
4.2: 3 h / 20 °C / pH Ca. 3
View Scheme
3-(4-aminophenyl)piperidine
19733-56-3

3-(4-aminophenyl)piperidine

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: L-Tartaric acid / acetonitrile / 10 °C / Reflux
2.1: sodium hydroxide; triethylamine; dmap / dichloromethane / 8 h / 20 °C
3.1: hexane / 18 h / Reflux
4.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
5.1: ammonium bicarbonate / methanol / 12 h / 100 °C
5.2: 3 h / 20 °C / pH Ca. 3
View Scheme
Multi-step reaction with 4 steps
1.1: acetonitrile / 10 °C / Reflux
1.2: 0.33 h
1.3: 8 h / 20 °C
2.1: hexane / 18 h / Reflux
3.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
4.1: ammonium bicarbonate / methanol / 12 h / 100 °C
4.2: 3 h / 20 °C / pH Ca.3
View Scheme
(3S)-3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester
1171197-20-8

(3S)-3-(4-aminophenyl)piperidine-1-carboxylic acid tert-butyl ester

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hexane / 18 h / Reflux
2.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
3.1: ammonium bicarbonate / methanol / 12 h / 100 °C
3.2: 3 h / 20 °C / pH Ca. 3
View Scheme
Multi-step reaction with 3 steps
1.1: hexane / 18 h / Reflux
2.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
3.1: ammonium bicarbonate / methanol / 12 h / 100 °C
3.2: 3 h / 20 °C / pH Ca.3
View Scheme
tert-butyl 3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}-piperidine-1-carboxylate
1038915-92-2

tert-butyl 3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}-piperidine-1-carboxylate

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trifluorormethanesulfonic acid / dichloromethane
2: ethanol / 0.5 h / Reflux
3: sodium hydroxide / water; ethyl acetate / 20 °C
View Scheme
1-benzyl-3-piperidone
40114-49-6

1-benzyl-3-piperidone

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -60 °C / Inert atmosphere
1.2: 8 h / Inert atmosphere; Reflux
2.1: acetonitrile / 10 °C / Reflux
2.2: 0.33 h
2.3: 8 h / 20 °C
3.1: hexane / 18 h / Reflux
4.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
5.1: ammonium bicarbonate / methanol / 12 h / 100 °C
5.2: 3 h / 20 °C / pH Ca.3
View Scheme
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene
171364-83-3

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -60 °C / Inert atmosphere
1.2: 8 h / Inert atmosphere; Reflux
2.1: acetonitrile / 10 °C / Reflux
2.2: 0.33 h
2.3: 8 h / 20 °C
3.1: hexane / 18 h / Reflux
4.1: sodium azide; 2,6-dimethylpyridine / N,N-dimethyl-formamide / 24 h / 120 °C
5.1: ammonium bicarbonate / methanol / 12 h / 100 °C
5.2: 3 h / 20 °C / pH Ca.3
View Scheme
C25H28BrNO5

C25H28BrNO5

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
2: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere
3: ammonia / acetonitrile / 2 h / 105 °C
4: sodium hydroxide / water / 20 - 35 °C
5: potassium carbonate; copper(I) bromide; 8-quinolinol; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane / N,N-dimethyl acetamide / 24 h / 110 °C / Inert atmosphere
6: methanesulfonic acid / o-xylene / 3 h / 40 °C
View Scheme
C13H19BrO6S2

C13H19BrO6S2

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ammonia / acetonitrile / 2 h / 105 °C
2: sodium hydroxide / water / 20 - 35 °C
3: potassium carbonate; copper(I) bromide; 8-quinolinol; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane / N,N-dimethyl acetamide / 24 h / 110 °C / Inert atmosphere
4: methanesulfonic acid / o-xylene / 3 h / 40 °C
View Scheme
4-(3S-piperidine-3-yl)bromobenzene
1335523-82-4

4-(3S-piperidine-3-yl)bromobenzene

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / water / 20 - 35 °C
2: potassium carbonate; copper(I) bromide; 8-quinolinol; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane / N,N-dimethyl acetamide / 24 h / 110 °C / Inert atmosphere
3: methanesulfonic acid / o-xylene / 3 h / 40 °C
View Scheme
(S)-3-(4-bromophenyl)piperidine-1-carboxylic acid tert-butyl ester
1476776-55-2

(S)-3-(4-bromophenyl)piperidine-1-carboxylic acid tert-butyl ester

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; copper(I) bromide; 8-quinolinol; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane / N,N-dimethyl acetamide / 24 h / 110 °C / Inert atmosphere
2: methanesulfonic acid / o-xylene / 3 h / 40 °C
View Scheme
C8H6N2O2

C8H6N2O2

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 0.5 h / 20 - 35 °C
1.2: 3 h / 45 °C
2.1: potassium carbonate; copper(I) bromide; 8-quinolinol; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane / N,N-dimethyl acetamide / 24 h / 110 °C / Inert atmosphere
3.1: methanesulfonic acid / o-xylene / 3 h / 40 °C
View Scheme
C12H15N3O

C12H15N3O

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; copper(I) bromide; 8-quinolinol; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane / N,N-dimethyl acetamide / 24 h / 110 °C / Inert atmosphere
2: methanesulfonic acid / o-xylene / 3 h / 40 °C
View Scheme
(S)-tert-butyl 3-(4-(7-(tert-butylcarbamoyl)-2H-indazol-2-yl)phenyl)piperidine-1-carboxylate
1476776-84-7

(S)-tert-butyl 3-(4-(7-(tert-butylcarbamoyl)-2H-indazol-2-yl)phenyl)piperidine-1-carboxylate

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
With methanesulfonic acid In o-xylene at 40℃; for 3h;
C11H15BrO2

C11H15BrO2

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere
2: ammonia / acetonitrile / 2 h / 105 °C
3: sodium hydroxide / water / 20 - 35 °C
4: potassium carbonate; copper(I) bromide; 8-quinolinol; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane / N,N-dimethyl acetamide / 24 h / 110 °C / Inert atmosphere
5: methanesulfonic acid / o-xylene / 3 h / 40 °C
View Scheme
(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

2-[4-((3S)-3-piperidinyl)phenyl]-2H-indazole-7-carboxamide p-toluenesulfonic acid salt
1038915-73-9

2-[4-((3S)-3-piperidinyl)phenyl]-2H-indazole-7-carboxamide p-toluenesulfonic acid salt

Conditions
ConditionsYield
In Isopropyl acetate; dimethyl sulfoxide; isopropyl alcohol at 5 - 70℃; Inert atmosphere;85%
In water at 20 - 30℃; for 4h; Inert atmosphere;110 g
(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

D-(+)-camphoric acid
124-83-4

D-(+)-camphoric acid

2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (1R,3S)-(+)-camphorate

2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (1R,3S)-(+)-camphorate

Conditions
ConditionsYield
In tetrahydrofuran; methanol at 20 - 40℃; for 72h;75%
(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

(R)-Mandelic Acid
611-71-2

(R)-Mandelic Acid

2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (R)-(-)-mandelate

2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (R)-(-)-mandelate

Conditions
ConditionsYield
In tetrahydrofuran; acetonitrile at 20 - 40℃; for 80h;50.6%
(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

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

(1S)-10-camphorsulfonic acid

2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (1S)-(+)-camsylate

2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (1S)-(+)-camsylate

Conditions
ConditionsYield
In tetrahydrofuran; acetonitrile at 20 - 40℃;37%
(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine
1038915-60-4

(3S)-3-[4-{7-(aminocarbonyl)-2H-indazol-2-yl}phenyl]piperidine

(3S)-3-[4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl]piperidinium chloride
1038915-64-8

(3S)-3-[4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl]piperidinium chloride

Conditions
ConditionsYield
With hydrogenchloride In water for 0.25h;

MK-4827 Specification

The MK-4827 is an organic compound with the formula C19H20N4O. The systematic name of this chemical is 2-{4-[(3S)-Piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide. With the CAS registry number 1038915-60-4, it is also named as 2H-indazole-7-carboxamide, 2-[4-[(3S)-3-piperidinyl]phenyl]-.

Physical properties about MK-4827 are: (1)ACD/LogP: 2.01; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1.511; (6)#H bond acceptors: 5; (7)#H bond donors: 3; (8)#Freely Rotating Bonds: 3; (9)Polar Surface Area: 72.94 Å2; (10)Index of Refraction: 1.705; (11)Molar Refractivity: 92.745 cm3; (12)Molar Volume: 238.638 cm3; (13)Polarizability: 36.767×10-24cm3; (14)Surface Tension: 56.836 dyne/cm; (15)Density: 1.343 g/cm3; (16)Flash Point: 234.188 °C; (17)Enthalpy of Vaporization: 72.488 kJ/mol; (18)Boiling Point: 463.619 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc2cn(nc2c(c1)C(=O)N)c3ccc(cc3)[C@@H]4CCCNC4
(2)InChI: InChI=1/C19H20N4O/c20-19(24)17-5-1-3-15-12-23(22-18(15)17)16-8-6-13(7-9-16)14-4-2-10-21-11-14/h1,3,5-9,12,14,21H,2,4,10-11H2,(H2,20,24)/t14-/m1/s1
(3)InChIKey: PCHKPVIQAHNQLW-CQSZACIVBN
(4)Std. InChI: InChI=1S/C19H20N4O/c20-19(24)17-5-1-3-15-12-23(22-18(15)17)16-8-6-13(7-9-16)14-4-2-10-21-11-14/h1,3,5-9,12,14,21H,2,4,10-11H2,(H2,20,24)/t14-/m1/s1
(5)Std. InChIKey: PCHKPVIQAHNQLW-CQSZACIVSA-N

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