![356068-94-5](/CAS/GIF/356068-94-5.gif)
Toceranib synthesis
- Product Name:Toceranib
- CAS Number:356068-94-5
- Molecular formula:C22H25FN4O2
- Molecular Weight:396.46
![1-(2-Aminoethyl)pyrrolidine](/CAS/GIF/7154-73-6.gif)
7154-73-6
223 suppliers
$15.00/1g
![5-((Z)-(5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid](/CAS/GIF/356068-93-4.gif)
356068-93-4
140 suppliers
$45.00/25mg
![Toceranib](/CAS/GIF/356068-94-5.gif)
356068-94-5
114 suppliers
$28.00/1mg
Yield: 77%
Reaction Conditions:
with (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate;triethylamine in DMF (N,N-dimethyl-formamide) at 20; for 2 h;
Steps:
5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (100 g) and dimethylformamide (500 ml) were stirred and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (221 g), 1-(2-aminoethyl) pyrrolidine (45.6 g) and triethylamine (93 ml) were added. The mixture was stirred for 2 hours at ambient temperature. The solid product was collected by vacuum filtration and washed with ethanol. The solids were slurry-washed by stirring in ethanol (500 ml) for one hour at 64 C and cooled to room temperature. The solids were collected by vacuum filtration, washed with ethanol, and dried under vacuum to give 5-[5-fluoro-2-oxo-1,2-dihydro-indol- (3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-pyrrolidin-1-yl-ethyl)-amide (101.5 g, 77 % yield). 1H-NMR (dimethylsulfoxide-d6) δ 1.60 (m, 4H, 2xCH2), 2.40, 2.44 (2xs, 6H, 2xCH3), 2.50 (m, 4H, 2xCH2), 2.57, 3.35 (2xm, 4H, 2XCH2), 7.53, 7.70, 7.73, 7.76 (4xm, 4H, aromatic and vinyl), 10.88 (s, 1H, CONH), 13.67 (s, 1H, pyrrole NH). MS m/z 396 [M+1].
References:
PHARMACIA & UPJOHN COMPANY WO2004/76410, 2004, A2 Location in patent:Page 12
![5-Formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid](/CAS/GIF/253870-02-9.gif)
253870-02-9
371 suppliers
$6.00/1g
![Toceranib](/CAS/GIF/356068-94-5.gif)
356068-94-5
114 suppliers
$28.00/1mg
![Ethyl 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylate](/CAS/GIF/2199-59-9.gif)
2199-59-9
241 suppliers
$8.00/250mg
![Toceranib](/CAS/GIF/356068-94-5.gif)
356068-94-5
114 suppliers
$28.00/1mg
![3,5-Dimethylpyrrole-2,4-dicarboxylic acid 2-t-butyl ester-4-ethyl ester](/CAS/GIF/86770-31-2.gif)
86770-31-2
148 suppliers
$19.78/1gm:
![Toceranib](/CAS/GIF/356068-94-5.gif)
356068-94-5
114 suppliers
$28.00/1mg
![1H-Pyrrole-3-carboxamide, 5-formyl-2,4-dimethyl-N-[2-(1-pyrrolidinyl)ethyl]-](/CAS/20210111/GIF/342642-56-2.gif)
342642-56-2
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![5-Fluoro-2-oxindole](/CAS/GIF/56341-41-4.gif)
56341-41-4
529 suppliers
$12.00/5g
![Toceranib](/CAS/GIF/356068-94-5.gif)
356068-94-5
114 suppliers
$28.00/1mg