Cangrelor Impurity 2 synthesis

5synthesis methods

Product Name:Cangrelor Impurity 2
CAS Number:847460-53-1
Molecular formula:C16H23F3N5O7PS2
Molecular Weight:549.48

(2R,3S,4R,5R)-2-(hydroxyMethyl)-5-(6-((2-(Methylthio)ethyl)aMino)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol

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847460-53-1
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Yield:847460-53-1 66.1%

Reaction Conditions:

with triethyl phosphate;N,N,N',N'-tetramethyl-1,8-diaminonaphthalene;trichlorophosphate at 0 - 5; for 8 h;Large scale;Temperature;

Steps:

3; 4

Will be 15Kg of Canggelorel intermediates III and10.3Kg 1,8 bis-dimethylaminonaphthalene inputs300 Kg of triethyl phosphate,Frozen brine cooled to 0 ~ 5 ,9.9 Kg of phosphorus oxychloride was added to the reaction solution.The mixture was stirred at 0 to 5 ° C for 8 hours,TLC detection of cangrero intermediate III was complete.To obtain a crude triphosphate solution of Canggelorel intermediate I,Purity of about 90%.
A crude triethyl phosphate solution of Cangrero intermediate I (which can be prepared as in Example 3) was transferred to 900 kg of ice water containing 41 Kg of sodium bicarbonate,And stirred for 1.5 hours.The aqueous phase was extracted three times with methyl t-butyl ether (900 Kg) and the organic phase was discarded.The aqueous phase was concentrated under reduced pressure (-0.08 MPa to -0.1 MPa) at 40 ° C until distilled off.To the residue was added 248 Kg of ethanol and stirred for 2 hours.Centrifuged and washed with 25 Kg of ethanol.The resulting solid was put in 240 Kg of deionized water, stirred and dissolved,The pH was adjusted to 2-3 with 1N hydrochloric acid, stirred for 1 hour, centrifuged and washed with 15 Kg of deionized water.The resulting solid solution was poured into 126 Kg of ethanol,Adding 15 kg of ammonia having a mass concentration of 25% (the mass concentration means that the mass of ammonia gas is the percentage of the total mass of the aqueous ammonia solution) is adjusted to pH 7-8,Stirred for 2 hours, centrifuged and washed with 15 Kg of deionized water.Wet goods 40 , -0.08MPa ~ -0.1MPa decompression,Dried at 20 ° C to 25 ° C for 16 hours to obtain 11.6 Kg of a white solid as a Canggellor intermediate I,Yield 66.1%.

References:

CN106674322,2017,A Location in patent:Paragraph 0046; 0048; 0049; 0050; 0051; 0052; 0053; 0054

43157-50-2 Synthesis

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References

(2R,3R,4S,5R)-2-(6-aMino-2-(3,3,3-trifluoropropylthio)-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol

163706-51-2
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847460-53-1
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References

Adenosine,N-acetyl-2-[(3,3,3-trifluoropropyl)thio]-,2',3',5'-triacetate (9CI)

163706-52-3
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847460-53-1
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References

(2R,3R,4R)-2-(acetoxyMethyl)-5-(6-(N-(2-(Methylthio)ethyl)acetaMido)-2-((3,3,3-trifluoropropyl)thio)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

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847460-53-1
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References