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341031-54-7

Basic Information
CAS No.: 341031-54-7
Name: Sunitinib malate
Article Data: 21
Cas Database
Molecular Structure:
Molecular Structure of 341031-54-7 (Sunitinib malate)
Formula: C22H27FN4O2.C4H6O5
Molecular Weight: 532.569
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);
EINECS: 638-825-9
Density: 1.3600g/mLat 25°C(lit.)
Melting Point: 189-191°C
Boiling Point: 572.1 °C at 760 mmHg
Flash Point: 299.8 °C
Solubility: N/A
Appearance: N/A
Hazard Symbols: T
Risk Codes: 61-2-48/25-36/37-22-53
Safety: 53-22-36/37-24/25
Transport Information: N/A
PSA: 172.06000
LogP: 2.77040
Synthetic route
97-67-6

(S)-Malic acid

557795-19-4

sunitinib

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%
56341-41-4

5-fluoroindol-2(3H)-one

97-67-6

(S)-Malic acid

356068-86-5

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

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;
56341-41-4

5-fluoroindol-2(3H)-one

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

356068-86-5

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

341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;80%
56341-41-4

5-fluoroindol-2(3H)-one

1200435-83-1

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

341031-54-7

sunitinib malate

Conditions
ConditionsYield
With pyrrolidine In butan-1-ol at 20℃; Reflux;75.1%
56341-41-4

5-fluoroindol-2(3H)-one

356068-86-5

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

341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;75%
56341-41-4

5-fluoroindol-2(3H)-one

di-(n-propyl ammonium) L-malate

356068-86-5

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

341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;75%
56341-41-4

5-fluoroindol-2(3H)-one

di-(diisopropyl ammonium) L-malate

356068-86-5

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

341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;72.5%
56341-41-4

5-fluoroindol-2(3H)-one

1332307-07-9

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

356068-86-5

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

341031-54-7

sunitinib malate

Conditions
ConditionsYield
In methanol; acetonitrile at 25 - 30℃; for 3h;72%
97-67-6

(S)-Malic acid

1374685-40-1

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

356068-86-5

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

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;
253870-02-9

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

56341-41-4

5-fluoroindol-2(3H)-one

97-67-6

(S)-Malic acid

100-36-7

N,N-diethylethylenediamine

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%
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    Product Name Sunitinib malate Synonyms Sunitinib malate;4-dimethyl-1H-pyrrole-3-carboxamide (2S)-hydroxybu CAS: 341031-54-7 MF: C22H27FN4O2.C4H6O5 M

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    Sunitinib malate CAS No.:341031-54-7 Name: Sunitinib malate Synonyms: 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 (2S)-hydrox

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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.

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