210101-16-9 Usage
Uses
Used in Pharmaceutical Industry:
Conivaptan is used as a vasopressin antagonist for the treatment of hyponatremia (low blood sodium levels) caused by the syndrome of inappropriate antidiuretic hormone (SIADH). By blocking the V1a and V2 receptors, Conivaptan helps to increase free water excretion and raise blood sodium levels, thus alleviating the symptoms of hyponatremia.
In addition to its primary use, Conivaptan may also have potential applications in other areas of medicine, such as the treatment of other conditions related to vasopressin dysregulation. However, further research and clinical trials would be necessary to establish its efficacy and safety in these contexts.
Synthesis
After looking at several different approaches to the synthesis, a convergent approach, shown in the Scheme 4, was developed
for large scale synthesis. Bromination of benzazepinone
10 with pyridinium hydrobromide perbromide in chloroform followed by recrystallization gave bromide 11.
Reaction of bromide 11 with ethaneimidate hydrochloride in
the presence of potassium carbonate in toluene or chloroform
gave the desired imidazole 12 in 69% yield. Although chlo-roform provided a slightly better yield, for large scale preparation,
toluene was used to minimize halogenated solvent
waste and because the quality of product was similar or better
than with use of chloroform. Deprotection of the tosylate
was found to be effective with heating the sulfonamide 12 in
80% sulfuric acid at 80oC. The benzazepinone product 13
was obtained in 90% yield after crystallization from acetonitrile
and water mixture.Synthesis of the coupling partner 16 required to provide
conivaptan was synthesized in 95% yield from biphenyl 2-
benzoic acid via sequential reaction with thionyl
chloride in toluene followed by coupling with aminobenzoic
acid in acetone with N,N-dimethylaniline as a base. High
quality acid 16 was obtained by crystallization from DMF
and water. The acid 16 was activated by converting it into
acid chloride with thionyl chloride in acenonitrile, to which
was added imidazo benzazepine 13 in toluene and, after recrystallization
in acidic ethanol, gave conivaptan hydrochloride
(III) in 90% yield.
Check Digit Verification of cas no
The CAS Registry Mumber 210101-16-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,1,0,1,0 and 1 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 210101-16:
(8*2)+(7*1)+(6*0)+(5*1)+(4*0)+(3*1)+(2*1)+(1*6)=39
39 % 10 = 9
So 210101-16-9 is a valid CAS Registry Number.
InChI:InChI=1/C32H26N4O2/c1-21-33-28-19-20-36(29-14-8-7-13-27(29)30(28)34-21)32(38)23-15-17-24(18-16-23)35-31(37)26-12-6-5-11-25(26)22-9-3-2-4-10-22/h2-18H,19-20H2,1H3,(H,33,34)(H,35,37)
