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Basic Information

Molecular Structure:
CAS No.:	341031-54-7
Name:	Sunitinib malate
Article Data:	21

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
Hazard Symbols:	T
Risk Codes:	61-2-48/25-36/37-22-53
Safety:	53-22-36/37-24/25
PSA:	172.06000
LogP:	2.77040

Synthetic route

: 97-67-6
(S)-Malic acid

: 557795-19-4
sunitinib

: 341031-54-7
sunitinib malate

Conditions

Conditions	Yield
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

Conditions	Yield
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

: 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

Conditions	Yield
In methanol; acetonitrile at 25 - 30℃; for 3h;	80%

...Expand

: 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

Conditions	Yield
With pyrrolidine In butan-1-ol at 20℃; Reflux;	75.1%

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

: 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

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

: 341031-54-7
sunitinib malate

Conditions

Conditions	Yield
In methanol; acetonitrile at 25 - 30℃; for 3h;	75%

...Expand

: 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

Conditions	Yield
In methanol; acetonitrile at 25 - 30℃; for 3h;	75%

...Expand

: 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

Conditions	Yield
In methanol; acetonitrile at 25 - 30℃; for 3h;	72.5%

...Expand

: 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

Conditions	Yield
In methanol; acetonitrile at 25 - 30℃; for 3h;	72%

...Expand

: 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

Conditions	Yield
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

: 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

Conditions	Yield
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

Raw Materials

443-69-6

97-67-6

100-36-7

Total:219 Page 1 of 6 1 2 3 4 5 6 Next>>

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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