Remdesivir impurity-1 synthesis
- Product Name:Remdesivir impurity-1
- CAS Number:1355049-95-4
- Molecular formula:C12H13N5O4
- Molecular Weight:291.27
![(3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile](/CAS/20211123/GIF/1191237-68-9.gif)
1191237-68-9
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1355049-95-4
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Yield:1355049-95-4 362 mg
Reaction Conditions:
with boron trichloride in dichloromethane at -78 - -40; for 2 h;
Steps:
4.4-1 Example 4-1
Add (2R,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy )-5-((Benzyloxy)methyl)tetrahydrofuran-2-carbonitrile (6.0g, 10.7mmol)Dissolve in anhydrous dichloromethane (60 mL) and cool to -78°C under nitrogen protection.Then add boron trichloride (1M, 40.6mL, 3.8eq.),The reaction mixture was heated to -40°C and stirred for 2 hours.Then the reaction mixture was cooled again to -78°C,And methanol (12 mL) was added dropwise.Add a solution of triethylamine (16mL) in methanol (24mL) dropwise,Finally, the reaction mixture was warmed to room temperature.The mixture was concentrated, and the remaining solid residue was dissolved in methanol (60 mL),And heated to 45°C.Water (60 mL) was added, and the resulting mixture was concentrated under reduced pressure at 45°C,To remove volatiles, and then wash with dichloromethane three times (30mL×3),Retain the water phase, and prepare the liquid phase through preparation and separation. The specific conditions for preparing the liquid phase are as follows:
References:
CN113493480,2021,A Location in patent:Paragraph 0016; 0095-0109
1191237-68-9
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1191237-69-0
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1355049-95-4
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1369903-46-7
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1355049-95-4
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![D-Ribofuranose, 1-C-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-2,3,5-tris-O-(phenylmethyl)-](/CAS/20200611/GIF/1355049-94-3.gif)
1355049-94-3
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1355049-95-4
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16838-89-4
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1191237-69-0
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$8.00/1mg
1355049-95-4
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