Tadalafil Impurity H
Tadalafil Impurity H is a structurally related byproduct arising from the synthetic pathway of tadalafil, characterized by a substituted pyrazine core with an oxazole ring in place of the thiazole moiety and an additional hydroxyl group at the 6-position. This impurity exhibits a distinct electronic configuration due to the oxygen substitution, leading to altered polarity and chromatographic behavior. It serves as a critical HPLC reference standard for quantifying residual impurities in tadalafil drug substances.
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Molecular Formula
C22H19N3O6
Molecular Weight
421.4000
CAS Number
1346605-38-6
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PubChem CID
71752283 ↗
IUPAC Name
(6R,14aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-6,8,14,14a-tetrahydro-3H-pyrazino[1,2-d][1,4]benzodiazonine-1,4,7,13-tetrone
Other CAS Numbers (also listed on PubChem)
1978322-98-3
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📝 Synonyms
Tadalafil Ketolactam
1346605-38-6
Tadalafil EP Impurity H
1978322-98-3
83Z1ZC7LN1
(6R,14aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-6,8,14,14a-tetrahydro-3H-pyrazino[1,2-d][1,4]benzodiazonine-1,4,7,13-tetrone
rel-(6R,14aR)-6-(1,3-Benzodioxol-5-yl)-2,3,14,14a-tetrahydro-2-methylpyrazino[1,2-d][1,4]benzodiazonine-1,4,7,13(6H,8H)-tetrone
rel-(6R,14aR)-6-(Benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,14,14a-tetrahydrobenzo[h]pyrazino[1,2-d][1,4]diazonine-1,4,7,13(6H,8H)-tetraone
(6R,14aR)-6-(1,3-Benzodioxol-5-yl)-2,3,14,14a-tetrahydro-2-methylpyrazino[1,2-d][1,4]benzodiazonine-1,4,7,13(6H,8H)-tetrone
(6R,14aR)-6-(Benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,14,14a-tetrahydrobenzo[h]pyrazino[1,2-d][1,4]diazonine-1,4,7,13(6H,8H)-tetraone
🔬 Chemical Identifiers
CN1CC(=O)N2[C@@H](C1=O)CC(=O)C3=CC=CC=C3NC(=O)[C@H]2C4=CC5=C(C=C4)OCO5
InChI=1S/C22H19N3O6/c1-24-10-19(27)25-15(22(24)29)9-16(26)13-4-2-3-5-14(13)23-21(28)20(25)12-6-7-17-18(8-12)31-11-30-17/h2-8,15,20H,9-11H2,1H3,(H,23,28)/t15-,20-/m1/s1
BBMXALYUYHSADD-FOIQADDNSA-N
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