ChemicalBook CAS DataBase List Tolvaptan

Tolvaptan synthesis

10synthesis methods

Product Name:Tolvaptan
CAS Number:150683-30-0
Molecular formula:C26H25ClN2O3
Molecular Weight:448.94

Tolvaptan is a selective, competitive vasopressin receptor 2 antagonist used to treat hyponatremia (low blood sodium levels) associated with congestive heart failure, cirrhosis, and the syndrome of inappropriate antidiuretic hormone (SIADH).

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

ROUTE 10

Cordero-Vargas, Alejandro; Quiclet-Sire, Beatrice; Zard, Samir Z. A flexible approach for the preparation of substituted benzazepines: Application to the synthesis of tolvaptan. Bioorganic & Medicinal Chemistry. Volume 14. Issue 18. Pages 6165-6173. 2006.

137973-76-3
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$59.00/2 mg

150683-30-0
344 suppliers
$25.00/1mg

Yield:150683-30-0 96%

Reaction Conditions:

with methanol;sodium tetrahydroborate at 0; for 2 h;

Steps:

1.7 (7) Preparation of N-[4-[(7-chloro-2,3,4,5-tetrahydro-5-hydroxy-1H-1-benzazepine-1-yl)carbonyl]-3-methylphenyl]-2-methylbenzamide
7-chloro-5-hydroxy-2,3,4,5-tetrahydro-1H-1- benzazepine (19.0g, 42.51mmol) was dissolved in methanol (200ml) in a solvent, at 0 for Conditional batch of sodium borohydride (2.42g, 63.77mmol), after the addition was complete stirring was continued for 2h, TLC the reaction was complete. The reaction mixture was poured into water, extracted with methylene chloride, dried over anhydrous sodium sulfate, filtration and vacuum distillation of crude with methanol: petroleum ether (2: 1) and recrystallized to give a white solid tolvaptan (18.33g , 96.0%).

References:

Shanghai Tin Tsz Bio Valley Biological Engineering Co.;Li, Xinjuanzi;Li, Jianzhi;Ma, Xilai;Chi, Wangzhou;Liu, Hai;Hu, Xuhua;Zheng, Xiaoli;Di, Zhijun;Li, Jianxun CN105315169, 2016, A Location in patent:Paragraph 0170; 0211; 0212

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