Tripamide

Tripamide
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 3-(aminosulfonyl)-4-chloro-N-[(3aR,4S,7R,7aS)-octahydro-2H-4,7-methanoisoindol-2-yl]benzamide;
CAS Number	73803-48-2;
PubChem CID	636401;
ChemSpider	4445396;
UNII	G36A0E9CVT;
ChEMBL	ChEMBL2104484;
CompTox Dashboard (EPA)	DTXSID2057817 ;
Chemical and physical data
Formula	C16H20ClN3O3S
Molar mass	369.86 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1C[C@@H]2C[C@H]1[C@@H]3[C@H]2CN(C3)NC(=O)C4=CC(=C(C=C4)Cl)S(=O)(=O)N;
	InChI InChI=1S/C16H20ClN3O3S/c17-14-4-3-11(6-15(14)24(18,22)23)16(21)19-20-7-12-9-1-2-10(5-9)13(12)8-20/h3-4,6,9-10,12-13H,1-2,5,7-8H2,(H,19,21)(H2,18,22,23)/t9-,10+,12-,13+; Key:UHLOVGKIEARANS-NIFPGPBJSA-N;
	(verify)

Tripamide (INN) is a diuretic.

Synthesis

Tripamide synthesis:[1]

Preparation starts by exhaustive reduction of the Diels-Alder adduct from cyclopentadiene and maleimide (1). Nitrosation of the product (2), followed by reduction of the nitroso group of 3, gives the corresponding hydrazine (4). Acylation with acid chloride 5 gives tripamide (6).

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References

U.S. Patent 3,787,440

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[1] U.S. Patent 3,787,440