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Structured search
18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
ChemicalBook CAS DataBase List Surufatinib
1308672-74-3

Surufatinib synthesis

1synthesis methods
Treatment of sulfonyl chloride 358 at room temperature using triethylamine and 2,2,2-trifluoroethanol (TFE) as solvents followed by hydrogenation afforded aniline 360. Exposure of 360 to DBU under microwave conditions generated an intermediate sulfinyl group. This intermediate sulfinyl group subsequently underwent nucleophilic attack by a commercial diamine, of which diamine 361 afforded the desired sulfonamide 362. Dichloropyrimidine 363 underwent a substitution reaction with hydroxyindole 364 to afford diaryl ether 365. Diaryl ether 365 then underwent a second substitution reaction with amine 362 under acidic conditions. Exposure of the product to a base in aqueous solution ultimately afforded surufatinib in 50% yield.
Surufatinib synthesis
5-((2-chloropyriMidin-4-yl)oxy)-2-Methyl-1H-indole

1071105-16-2
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1-(3-aMinophenyl)-N-(2-(diMethylaMino)ethyl)MethanesulfonaMide

1094797-87-1
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Surufatinib

1308672-74-3
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Yield:-

Reaction Conditions:

with toluene-4-sulfonic acid in N,N-dimethyl-formamide at 55 - 65;

Steps:

1.2
To a 10 L three-necked round bottom flask, equipped with amechanical stirrer and a thermometer, were added Compound 3 (1 .05 Kg), 1 -(3- aminophenyl)-/V-(2-(dimethylamino)ethyl)methanesulfonamide (Compound 4, 1.06 Kg), p-toluenesulfonic acid (0.86 Kg), and /VJV-dimethylformamide (5.25 L). The reaction mixture was carefully warmed to a temperature ranging from 55 to 65 °C, and stirred at this temperature for 16-20 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature, and was transferred portion-wise to a solution of 5% aqueous potassium carbonate.When the addition was complete, the obtained slurry was stirred for another 1 -2 hours. Crude product was collected by filtration, and the wet filter cake was transferred to a 200 L reactor.[0116] To the reactor, toluene (104 Kg) was added, and the suspension was heated to reflux to remove water by a Dean-Stark trap. After the removal of water, the solution was concentrated to a final volume of 30-40 L under reduced pressure, cooled to 15-20 °C. The product was collected and dried to afford the title product (Compound of Formula A, 1.07 Kg). This material can then be used to produce novel forms of the compound of Formula A, such as Form I and/or Form II.

References:

Location in patent:Page/Page column 27

Surufatinib Related Search:

2-Methylindole