ABC00786LR

2,3-Dehydro Ketoconazole

2,3-Dehydro Ketoconazole is a synthetic byproduct of Ketoconazole featuring a conjugated 2,3-double bond in the terminal side chain, replacing the saturated methylene group. This structural modification introduces a trans-alkene functionality adjacent to the 1,2,4-triazole moiety, while retaining the core 4-(4-chlorophenyl)-1-(1H-1,2,4-triazol-1-ylmethyl)butan-1-one scaffold. The compound retains two chloroaromatic substituents and a ketone at C-1, but exhibits altered electronic properties due to the unsaturated side chain. It arises via oxidative elimination during API synthesis, specifically during triazole coupling steps. Functions as an HPLC reference standard for quantifying dehydrogenation impurities in Ketoconazole formulations.

On Request
Molecular Formula C26H26Cl2N4O4
Molecular Weight 529.4000
CAS Number 254912-63-5 โœ“ Verified
PubChem CID 71315319 โ†—
Purity N/A
Product Type API Impurity
Parent Drug Ketoconazole
Lead Time On Request
IUPAC Name 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-2,3-dihydropyrazin-1-yl]ethanone

๐Ÿ“ Synonyms

254912-63-5 2,3-Dehydro Ketoconazole 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-2,3-dihydropyrazin-1-yl]ethanone 1-(4-(4-((Trans-2-((1H-imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-3,4-dihydropyrazin-1(2H)-yl)ethanone R-049223 54OX2F5ST1 Ketoconazole EP Impurity A (+/-)-1-Acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)1,2,3,4-tetrahydropyrazine 1-Acetyl-4-(4-(((2RS,4SR)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)1,2,3,4-tetrahydropyrazine Ethanone, 1-(4-(4-(((2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-3,4-dihydro-1(2H)-pyrazinyl)-, rel-

๐Ÿ”ฌ Chemical Identifiers

CC(=O)N1CCN(C=C1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
InChI=1S/C26H26Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-10,12,14,18,23H,11,13,15-17H2,1H3/t23-,26-/m0/s1
GHVFISLXKPKRQU-OZXSUGGESA-N

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