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Sunitinib Malate manufacture
Cas No: 341031-54-7
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Sunitinib malate CAS:341031-54-7
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Sunitinib Malate high purity 98%
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Sunitinib Malate
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High purity Various Specifications Sunitinib malate CAS:341031-54-7
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Sunitinib Malate 341031-54-7 API
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341031-54-7 Sunitinib malate
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Sunitinib Malate
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Sunitinib Malate
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341031-54-7 Usage

Anticancer drug

Sunitinib malate is a kind of novel oral multi-targeted anticancer drugs and belongs to multi-targeted tyrosine kinase inhibitor with its trade name being “suntent”. It was successfully developed by Pfizer Company and has dual anti-tumor effect. Moreover, it is the only therapeutic drug which can go beyond the 2-year survival period of advanced kidney cancer and plays a central role in the field of carcinoma and gastrointestinal stromal tumor therapeutic areas. It entered into market in February 2006 in the United States. This drug was the first anti-cancer drug which was approved by the US FDA and can simultaneously treat two diseases.
Sunitinib exerts its therapeutic role through preventing the tumor cells from getting the blood and nutrients needed for growth. Clinical trials have showed that the drug can delay the growth rate of gastrointestinal stromal tumors, and can shrink the size of renal cell tumors. Sunitinib malate is the first novel targeted drug being capable of selectively targets drugs for a variety of new tyrosine kinase receptors. It combine two kinds of anti-tumor mechanisms including both stopping the formation of anti-angiogenic which is responsible for supplying blood to tumor and direct attack of tumor cells. It represents the advent of a new round of targeted therapies, being able to attack the tumor directly without the toxicity of the conventional chemotherapy.
The indications of Sunitinib malate are as follows:
1, Patients who failed in the treatment with matinib mesylate or of intolerant gastrointestinal stromal tumors (GIST).
2, inoperable advanced renal cell carcinoma (RCC).
3, advanced pancreatic endocrine tumors.
The above information is edited by the Chemicalbook of Dai Xiongfeng.

Uses

Sunitinib Malate (Sutent, SU11248) is a multi-targeted RTK inhibitor targeting VEGFR2 (Flk-1) and PDGFRβ with IC50 of 80 nM and 2 nM, and also inhibits c-Kit.

Uses

Anti-cancer drugs

Uses

A multi-kinase inhibitor targeting several receptor tyrosine kinases (RTK). Antineoplastic.

Uses

Sunitinib Malate is a multi-targeted RTK inhibitor targeting VEGFR2 (Flk-1) and PDGFRβ with IC50 of 80 nM and 2 nM, and also inhibits c-Kit

Chemical Properties

Yellow Solid

Biological Activity

Potent, ATP-competitive VEGFR, PDGFR β and KIT inhibitor (K i values are 2, 9, 17, 8 and 4 nM for VEGFR -1, -2, -3, PDGFR β and KIT respectively). Also inhibits cellular receptor phosphorylation of FLT3, RET and CSF-1R. Exhibits antiangiogenic and antitumor activity in multiple xenograft models.

Brand name

(Pfizer).
InChI:InChI=1/C23H30N4O2.C5H8O5/c1-6-27(7-2)11-10-24-23(29)21-15(4)20(25-16(21)5)13-18-17-12-14(3)8-9-19(17)26-22(18)28;6-3(5(9)10)1-2-4(7)8/h8-9,12-13,25H,6-7,10-11H2,1-5H3,(H,24,29)(H,26,28);3,6H,1-2H2,(H,7,8)(H,9,10)/b18-13-;/t;3-/m.0/s1

341031-54-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Sunitinib Malate

1.2 Other means of identification

Product number -
Other names sunitynib L-malate

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:341031-54-7 SDS

341031-54-7Synthetic 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;
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%
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

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%
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%
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%
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%
(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;
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%
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%
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%
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;

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