ChemicalBook CAS DataBase List Lotilaner

Lotilaner synthesis

4synthesis methods

Product Name:Lotilaner
CAS Number:1369852-71-0
Molecular formula:C20H14Cl3F6N3O3S
Molecular Weight:596.76

2-Thiophenecarboxylic acid, 5-[4,5-dihydro-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-3-isoxazolyl]-3-methyl-

1613733-74-6
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2-AMino-N-(2,2,2-trifluoroethyl)acetaMide hydrochloride

1171331-39-7
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$45.00/50mg

1369852-71-0
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Yield:1369852-71-0 72%

Reaction Conditions:

with O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate;triethylamine in N,N-dimethyl-formamide; pH=10 at 20; for 0.666667 h;

Steps:

3.3.3 3.3 Condensation reaction
Add to the 100ml reaction flaskIntermediate 4 (10.74g),HBTU (10.71g, 28.09mmol),DMF (20ml),Intermediate 5, mix well and add triethylamine,Make the pH of the mixed liquid system=10,Stir at room temperature for 40 minutes, TLC monitors the progress of the reaction,After full reaction,Add 40ml of water, stir and crystallize,Suction filtration, wash the filter cake with 20ml water,Dry the filter cake under reduced pressure,Then use a mixture of ethyl acetate and petroleum ether (1:2) or ethanolAnd water (1:2) mixture to recrystallize,Product undergoes chiral resolution (chiral resolution)Obtain the white powder product lotirana 1-3, (10.06g,72% yield, 99.64% purity),The structure of lotirana 1-3 was determined by HNMRThe rate and purity are determined by chromatogram HPLC,As shown in Figure 5 and Figure 6.

References:

CN112457267, 2021, A Location in patent:Paragraph 0032; 0036; 0037; 0038

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Isoxazole, 3-(5-bromo-4-methyl-2-thienyl)-4,5-dihydro-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-

1613733-73-5
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1369852-71-0
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References

1613733-74-6
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1369852-71-0
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References

5-BROMO-3-METHYLTHIOPHENE-2-CARBOXYLIC ACID

38239-45-1
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$26.00/100mg

1369852-71-0
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References