Product Name

  • Name

    Sunitinib malate

  • EINECS 638-825-9
  • CAS No. 341031-54-7
  • Article Data21
  • CAS DataBase
  • Density 1.3600g/mLat 25°C(lit.)
  • Solubility
  • Melting Point 189-191°C
  • Formula C22H27FN4O2.C4H6O5
  • Boiling Point 572.1 °C at 760 mmHg
  • Molecular Weight 532.569
  • Flash Point 299.8 °C
  • Transport Information
  • Appearance
  • Safety 53-22-36/37-24/25
  • Risk Codes 61-2-48/25-36/37-22-53
  • Molecular Structure Molecular Structure of 341031-54-7 (Sunitinib malate)
  • Hazard Symbols T
  • Synonyms N-(2-diethylaminoethyl)-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide; (2S)-2-hydroxybutanedioic acid;Butanedioic acid, hydroxy-, (2S)-, compd. with N-(2-(diethylamino)ethyl)-5-((Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide (1:1);PHA-290940AD;1H-Pyrrole-3-carboxamide, N-(2-(diethylamino)ethyl)-5-((Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl)-2,4-dimethyl-, (2S)-hydroxybutanedioate (1:1);Sunitinib malate [USAN];SU011248 L-malate salt;SU010398;SU 011248;Sunitinib malate(TINIBS);
  • PSA 172.06000
  • LogP 2.77040

Synthetic route

(S)-Malic acid
97-67-6

(S)-Malic acid

sunitinib
557795-19-4

sunitinib

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; ethanol at 20℃; for 2h; Darkness;100%
In ethanol for 2 - 4h; Product distribution / selectivity; Reflux; Industry scale;93.6%
In ethanol for 2 - 4h; Product distribution / selectivity; Reflux;93.6%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

(S)-Malic acid
97-67-6

(S)-Malic acid

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
With pyrrolidine In ethanol at 78℃; for 3h;80%
With pyrrolidine In ethanol at 78℃; for 3h;80%
Stage #1: (S)-Malic acid; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide In butan-1-ol at 48℃;
Stage #2: 5-fluoroindol-2(3H)-one With pyrrolidine In butan-1-ol at 94℃; Product distribution / selectivity;		71.2%
Stage #1: 5-fluoroindol-2(3H)-one; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide In ethanol at 8 - 10℃; Reflux;
Stage #2: (S)-Malic acid In ethanol for 4 - 6h; Product distribution / selectivity; Reflux;		71%
Stage #1: (S)-Malic acid; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide In tetrahydrofuran for 4 - 6h;
Stage #2: 5-fluoroindol-2(3H)-one In tetrahydrofuran for 4 - 6h; Product distribution / selectivity; Reflux;
...Expand
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

2-(N,N-diethylamino)ethyl ammonium di(L-malate)

2-(N,N-diethylamino)ethyl ammonium di(L-malate)

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;80%
...Expand
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

L-(-)-malic acid of 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide
1200435-83-1

L-(-)-malic acid of 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
With pyrrolidine In butan-1-ol at 20℃; Reflux;75.1%
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

L-malic acid ; ammonium-L malate
2689-91-0, 4601-92-7, 5972-71-4, 6283-27-8, 18841-14-0, 18841-15-1, 20261-05-6, 54944-40-0, 85273-27-4, 85273-28-5, 102607-29-4

L-malic acid ; ammonium-L malate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;75%
...Expand
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

di-(n-propyl ammonium) L-malate

di-(n-propyl ammonium) L-malate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;75%
...Expand
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

di-(diisopropyl ammonium) L-malate

di-(diisopropyl ammonium) L-malate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;72.5%
...Expand
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

2-(N,N-diethylamino)ethyl ammonium L-malate
1332307-07-9

2-(N,N-diethylamino)ethyl ammonium L-malate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;72%
...Expand
(S)-Malic acid
97-67-6

(S)-Malic acid

5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole
1374685-40-1

5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Stage #1: 5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile for 13h; Reflux;
Stage #2: (S)-Malic acid In methanol; acetonitrile at 20℃; for 22h;		70%
Stage #1: 5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 13h; Reflux;
Stage #2: (S)-Malic acid In methanol for 24h;
Stage #1: 5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole; N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 9.5h; Reflux;
Stage #2: (S)-Malic acid In methanol for 24h;
...Expand
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
253870-02-9

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

(S)-Malic acid
97-67-6

(S)-Malic acid

N,N-diethylethylenediamine
100-36-7

N,N-diethylethylenediamine

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Stage #1: 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid; N,N-diethylethylenediamine With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In tetrahydrofuran for 20h;
Stage #2: (S)-Malic acid In tetrahydrofuran for 4 - 6h; Reflux;
Stage #3: 5-fluoroindol-2(3H)-one In tetrahydrofuran for 4 - 6h; Product distribution / selectivity; Reflux;		67%
...Expand
2-(N,N-diethylamino)ethyl ammonium L-malate
1332307-07-9

2-(N,N-diethylamino)ethyl ammonium L-malate

5-fluoro-2-oxindole
1032268-12-4

5-fluoro-2-oxindole

C14H24N3O5S(1-)*Na(1+)
1338703-87-9

C14H24N3O5S(1-)*Na(1+)

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;67%
...Expand
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

dipyrrolidine L-malate

dipyrrolidine L-malate

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;32%
...Expand
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyrrolidine / methanol / 5 - 7 h / Reflux
2: ethanol / 2 - 4 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane / acetonitrile / 7 h / Reflux
1.2: 3 h / 20 - 60 °C
2.1: methanol / 0.5 h / 20 °C / Inert atmosphere
2.2: 25 °C
View Scheme
ethyl (5-formyl-2,4-dimethyl-1H-pyrrole)-3-carboxylate
2199-59-9

ethyl (5-formyl-2,4-dimethyl-1H-pyrrole)-3-carboxylate

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C
2.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h
2.2: 16 h / 25 - 30 °C
3.1: pyrrolidine / methanol / 5 - 7 h / Reflux
4.1: ethanol / 2 - 4 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C
2.1: triethylamine; dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 20 h
2.2: 4 - 6 h / Reflux
2.3: 4 - 6 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C
2.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h
2.2: 16 h / 25 - 30 °C
3.1: ethanol / 8 - 10 °C / Reflux
3.2: 4 - 6 h / Reflux
View Scheme
2-tert-butyl 4-ethyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate
86770-31-2

2-tert-butyl 4-ethyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogenchloride / isopropyl alcohol / 25 - 50 °C
2.1: trichlorophosphate / 2 - 3 h / 0 - 50 °C
2.2: 25 - 30 °C / pH 12 - 13
3.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C
4.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h
4.2: 16 h / 25 - 30 °C
5.1: pyrrolidine / methanol / 5 - 7 h / Reflux
6.1: ethanol / 2 - 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogenchloride / isopropyl alcohol / 25 - 50 °C
2.1: trichlorophosphate / 2 - 3 h / 0 - 50 °C
2.2: 25 - 30 °C / pH 12 - 13
3.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C
4.1: triethylamine; dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 20 h
4.2: 4 - 6 h / Reflux
4.3: 4 - 6 h / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: hydrogenchloride / isopropyl alcohol / 25 - 50 °C
2.1: trichlorophosphate / 2 - 3 h / 0 - 50 °C
2.2: 25 - 30 °C / pH 12 - 13
3.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C
4.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h
4.2: 16 h / 25 - 30 °C
5.1: ethanol / 8 - 10 °C / Reflux
5.2: 4 - 6 h / Reflux
View Scheme
5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
253870-02-9

5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h
1.2: 16 h / 25 - 30 °C
2.1: pyrrolidine / methanol / 5 - 7 h / Reflux
3.1: ethanol / 2 - 4 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h
1.2: 16 h / 25 - 30 °C
2.1: ethanol / 8 - 10 °C / Reflux
2.2: 4 - 6 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane / ammonium sulfate / 5 h / Reflux
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h
2.2: 25 °C
3.1: N,N-dimethyl-formamide / 25 °C
4.1: methanol / 8 h / 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane / 5 h / Reflux
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / 25 °C
2.2: 1 h / 40 °C
3.1: acetonitrile; N,N-dimethyl-formamide / 1 h / 25 °C
4.1: methanol / 0.5 h / 20 °C / Inert atmosphere
4.2: 25 °C
View Scheme
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 2 h / 35 °C / Large scale
1.2: 2 h / 35 °C / Large scale
2.1: triethylamine / 2 h / 60 °C / Large scale
3.1: methanol / 1 h / 40 °C / Large scale
View Scheme
5-fluoro-1H-indole-2,3-dione
443-69-6

5-fluoro-1H-indole-2,3-dione

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrazine / 5.5 h / 100 - 130 °C
2: pyrrolidine / methanol / 5 - 7 h / Reflux
3: ethanol / 2 - 4 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: hydrazine / 5.5 h / 100 - 130 °C
2.1: ethanol / 8 - 10 °C / Reflux
2.2: 4 - 6 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: hydrazine / 5.5 h / 100 - 130 °C
2.1: triethylamine; dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 20 h
2.2: 4 - 6 h / Reflux
2.3: 4 - 6 h / Reflux
View Scheme
2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester
2199-51-1

2,4-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: trichlorophosphate / 2 - 3 h / 0 - 50 °C
1.2: 25 - 30 °C / pH 12 - 13
2.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C
3.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h
3.2: 16 h / 25 - 30 °C
4.1: pyrrolidine / methanol / 5 - 7 h / Reflux
5.1: ethanol / 2 - 4 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: trichlorophosphate / 2 - 3 h / 0 - 50 °C
1.2: 25 - 30 °C / pH 12 - 13
2.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C
3.1: triethylamine; dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 20 h
3.2: 4 - 6 h / Reflux
3.3: 4 - 6 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: trichlorophosphate / 2 - 3 h / 0 - 50 °C
1.2: 25 - 30 °C / pH 12 - 13
2.1: potassium hydroxide; water / methanol / 4 - 6 h / 60 - 70 °C
3.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / tetrahydrofuran / 0.5 h
3.2: 16 h / 25 - 30 °C
4.1: ethanol / 8 - 10 °C / Reflux
4.2: 4 - 6 h / Reflux
View Scheme
N,N-diethylethylenediamine
100-36-7

N,N-diethylethylenediamine

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol / 1 h / 25 - 30 °C
2: acetonitrile; methanol / 3 h / 25 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1: methanol / 1 h / 25 - 30 °C
2: acetonitrile; methanol / 3 h / 25 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1.1: p-toluenesulfonyl chloride / N,N-dimethyl-formamide / 0.25 h / 15 - 19 °C
1.2: 15 - 19 °C
1.3: 0.67 h / 13 - 16 °C
2.1: methanol / 25 - 30 °C
View Scheme
Multi-step reaction with 6 steps
1.1: dichloromethane / 0.5 h / 0 - 20 °C
2.1: zinc / methanol; acetic acid / 65 - 70 °C
3.1: sulfuric acid / water; methanol / 3.5 h / 60 - 65 °C
4.1: oxalyl dichloride / dichloromethane / 2.5 h / 0 - 10 °C / Inert atmosphere
4.2: 30 °C
5.1: potassium hydroxide / N,N-dimethyl-formamide / 3.5 h / 20 °C / Darkness; Inert atmosphere
6.1: methanol; ethanol / 2 h / 20 °C / Darkness
View Scheme
Multi-step reaction with 3 steps
1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / acetonitrile / 2 h / 35 °C / Large scale
1.2: 2 h / 35 °C / Large scale
2.1: triethylamine / 2 h / 60 °C / Large scale
3.1: methanol / 1 h / 40 °C / Large scale
View Scheme
N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide
356068-86-5

N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydrogensulfite / ethanol; water / 10 - 20 °C
2: acetonitrile; methanol / 3 h / 25 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane / ammonium sulfate / 5 h / Reflux
1.2: 29.3 h / Reflux
2.1: methanol / 8 h / 25 °C / Inert atmosphere
View Scheme
5-fluoroindol-2(3H)-one
56341-41-4

5-fluoroindol-2(3H)-one

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane / ammonium sulfate / 5 h / Reflux
1.2: 29.3 h / Reflux
2.1: methanol / 8 h / 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: ammonium sulfate / Inert atmosphere; Reflux
2.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 13 h / Reflux
2.2: 22 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: ammonium sulfate / Inert atmosphere; Reflux
2: trimethylsilyl trifluoromethanesulfonate / N,N-dimethyl-formamide; acetonitrile / Reflux
3: methanol / 8 h / 25 °C / Inert atmosphere
View Scheme
5-((Z)-(5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid
356068-93-4

5-((Z)-(5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h
1.2: 25 °C
2.1: N,N-dimethyl-formamide / 25 °C
3.1: methanol / 8 h / 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h / 25 °C
1.2: 1 h / 40 °C
2.1: acetonitrile; N,N-dimethyl-formamide / 1 h / 25 °C
3.1: methanol / 0.5 h / 20 °C / Inert atmosphere
3.2: 25 °C
View Scheme
Multi-step reaction with 2 steps
1.1: p-toluenesulfonyl chloride / N,N-dimethyl-formamide / 0.25 h / 15 - 19 °C
1.2: 15 - 19 °C
1.3: 0.67 h / 13 - 16 °C
2.1: methanol / 25 - 30 °C
View Scheme
(Z)-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl 5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate
452105-55-4

(Z)-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl 5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 25 °C
2: methanol / 8 h / 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: acetonitrile; N,N-dimethyl-formamide / 1 h / 25 °C
2.1: methanol / 0.5 h / 20 °C / Inert atmosphere
2.2: 25 °C
View Scheme
N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidine)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide, hydrochloride

N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidine)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide, hydrochloride

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 90 °C / pH 8 - 9
2: methanol / 8 h / 25 °C / Inert atmosphere
View Scheme
sunitinib mesylate

sunitinib mesylate

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water / 80 °C / pH 8 - 9
2: methanol / 8 h / 25 °C / Inert atmosphere
View Scheme
5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole
1374685-40-1

5-fluoro-1-(trimethylsilyl)-2-(trimethylsilyloxy)-1H-indole

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trimethylsilyl trifluoromethanesulfonate / N,N-dimethyl-formamide; acetonitrile / Reflux
2: methanol / 8 h / 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane / trifluorormethanesulfonic acid / acetonitrile / 48 h / 20 - 65 °C
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h
2.2: 25 °C
3.1: N,N-dimethyl-formamide / 25 °C
4.1: methanol / 8 h / 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile; N,N-dimethyl-formamide / Reflux
2.1: methanol / 0.5 h / 20 °C / Inert atmosphere
2.2: 25 °C
View Scheme
sunitinib hydrochloride
1327155-72-5

sunitinib hydrochloride

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: water / 90 °C
2.1: methanol / 0.5 h / 20 °C / Inert atmosphere
2.2: 25 °C
View Scheme
sunitinib methanesulfonic acid
1275588-72-1

sunitinib methanesulfonic acid

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: water / 80 °C
2.1: methanol / 0.5 h / 20 °C / Inert atmosphere
2.2: 25 °C
View Scheme
N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide
590424-05-8

N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

sunitinib malate
341031-54-7

sunitinib malate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxalyl dichloride / dichloromethane / 2.5 h / 0 - 10 °C / Inert atmosphere
1.2: 30 °C
2.1: potassium hydroxide / N,N-dimethyl-formamide / 3.5 h / 20 °C / Darkness; Inert atmosphere
3.1: methanol; ethanol / 2 h / 20 °C / Darkness
View Scheme
sunitinib malate
341031-54-7

sunitinib malate

(Z)-N-[2-(diethylamino)ethyl]-5-[(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-yliden)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide L-malate

(Z)-N-[2-(diethylamino)ethyl]-5-[(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-yliden)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide L-malate

Conditions
ConditionsYield
In ethanol Product distribution / selectivity; Reflux;

Sunitinib malate Analytical Methods

Sunitinib inhibits cellular signaling by targeting multiple receptor tyrosine kinases.These include all receptors for platelet-derived growth factor  and vascular endothelial growth factor receptors ,which play a role in both tumor angiogenesis and tumor cell proliferation. The simultaneous inhibition of these targets therefore leads to both reduced tumor vascularization and cancer cell death, and ultimately tumor shrinkage.

Sunitinib malate Specification

1. Introduction of Sunitinib malate

Sunitinib malate, with the IUPAC Name of N-(2-diethylaminoethyl)-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene) methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide; (2S)-2-hydroxybutanedioic acid, is one kind of yellow solid.

2. Properties of Sunitinib malate

Sunitinib malate has the following properties: (1)Flash Point: 299.8 °C; (2)Enthalpy of Vaporization: 85.77 kJ/mol; (3)Boiling Point: 572.1 °C at 760 mmHg; (4)Vapour Pressure: 4.24E-13 mmHg at 25°C.

3. Structure Descriptors of Sunitinib malate

You could convert the following datas into the molecular structure:
(1).InChI:InChI=1S/C22H27FN4O2.C4H6O5/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28;5-2(4(8)9)1-3(6)7/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28);2,5H,1H2,(H,6,7)(H,8,9)/b17-12-;/t;2-/m.0/s1 
(2).InChIKey:InChIKey=LBWFXVZLPYTWQI-IPOVEDGCSA-N 
(3).Smiles:c1c(F)cc2\C(C(Nc2c1)=O)=C\c1[nH]c(c(C(NCCN(CC)CC)=O)c1C)C.C([C@@H](C(=O)O)O)C(O)=O

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