63719-21-1

Basic information

• Product Name: PERGOLIDE MESYLATE INTERMEDIATE
• Synonyms: PERGOLIDE MESYLATE INTERMEDIATE
• CAS NO: 63719-21-1
• Molecular Formula: C₁₈H₂₄N₂O
• Molecular Weight: 284.4
• Mol File: 63719-21-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: PERGOLIDE MESYLATE INTERMEDIATE(CAS DataBase Reference)
• NIST Chemistry Reference: PERGOLIDE MESYLATE INTERMEDIATE(63719-21-1)
• EPA Substance Registry System: PERGOLIDE MESYLATE INTERMEDIATE(63719-21-1)

Safety Data

• Hazardous Substances Data: 63719-21-1(Hazardous Substances Data)

Upstream product

• 3006-19-7 9,10-dihydrolysergic acid methyl ester 
• 107-08-4 1-iodo-propane 
• 5878-43-3 9,10-dihydrolysergic acid 
• 63719-09-5 6-nor-6-n-propyl-9,10-dihydrolysergic acid methyl ester 
• 51260-62-9 D-6-cyano-8β-methoxycarbonylergoline 
• 30341-92-5 methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate 
• 18051-16-6 9,10-dihydrolysergol 

Downstream Products

• 66104-23-2 pergolide mesylate 
• 72821-83-1 D-6-propyl-8β-mesyloxymethylergoline 
• 66104-22-1 pergolide 
• 79675-18-6 Toluene-4-sulfonic acid (6aR,9R,10aR)-7-propyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester 

Relevant articles and documents

Simple and selective one-pot replacement of the N-methyl group of tertiary amines by quaternization and demethylation with sodium sulfide or potassium thioacetate: An application to the synthesis of pergolide

The paper describes a mild, selective, and rapid replacement of an N-methyl group of tertiary amines with other alkyl groups via a simple one-pot procedure. This transformation is easily achieved by preparation of the appropriate quaternary ammonium salt in sulfolane and in situ treatment with sodium sulfide or potassium thioacetate. The protocol is successfully applied to the transformation of dihydrolysergol, dextromethorphan and laudanosine (as models of ergot and opium N-methyl alkaloids) into various N-alkyl congeners.

Development of a practical high-yield industrial synthesis of pergolide mesylate

The development of a high-yield and low environmental impact synthesis able to deliver highly pure pergolide mesylate 1 is described. The process [seven chemical steps (four telescoped), three steps of isolation of intermediate, and only one drying] affords pergolide mesylate 1 in 75-81% overall yield from dihydrolysergic acid 4 with >99.8% purity.

Synthesis and structure-activity relationships of new (5R,8R,10R)-ergoline derivatives with antihypertensive or dopaminergic activity

A series of new (5R,8R,10R)-ergoline derivatives was synthesized, and their antihypertensive and dopaminergic activities were tested in conscious spontaneously hypertensive rats and in rats with unilateral 6- hydroxydopamine-induced lesions of the substantia nigra. (5R,8R,10R)-6- Alkyl-8-ergolinemethanols, prepared from the corresponding ergolinecarboxylates, were converted to the tosylates, which were treated with various five-membered heterocycles containing nitrogen atoms to afford the new ergolines. (5R,8R,10R)-8-(1,2,4-Triazol-1-ylmethyl)-6-methylergoline (4s, maleate: BAM-1110) exhibited potent dopaminergic activity, about 18- fold greater than that of bromocriptine mesylate. (5R,8R,10R)-8-(1,2,4- Triazol-1-ylmethyl)-6-propylergoline (8b, fumarate: BAM-1602) showed extremely potent dopaminergic activity, being about 220 and 1.15 times more active than bromocriptine mesylate and pergolide mesylate, respectively. Several compounds exhibited potent antihypertensive activity. Structure- activity relationships for antihypertensive and dopaminergic activities are discussed.

Ergot derivatives

Compounds and process for making same are disclosed, the compounds having the formula (I): STR1 wherein R1 represents methyl, phenyl, piperidino, 1-pyrrolidinyl, morpholino or 4-methyl-1-piperazinyl, alkyl or alkoxy having from 1 to 4 carbon atoms, amino, substituted amino of the formula NHR' (wherein R' is alkyl having from 1 to 4 carbon atoms, cycloalkyl, a benzyl, or phenyl) or substituted amino of the formula NR" R"' (wherein R" and R"' both represent alkyl having from 1 to 4 carbon atoms); R2 represents a hydrogen atom, alkyl having from 1 to 4 carbon atoms, or phenyl; R3 represents a fluorine atom, cyano, difluoromethyl, difluorobromomethyl, trifluoromethyl, methylthio, methylsulphonyl, sulphonamido, an alkoxy having from 1 to 4 carbon atoms, an alkanoyl having from 2 to 5 carbon atoms, or benzoyl; R4 represents a hydrocarbon having from 1 to 4 carbon atoms; R5 represents a hydrogen atom or methoxy; R6 represents a hydrogen or halogen atom or methyl; and R7 represents a hydrogen atom or methyl. The 2-cyano derivatives are especially preferred. The compounds are useful as antihypertensive agents.

6-N-Propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds

6-n-Propyl (ethyl or allyl)-8β-methoxy-(methylsulfinyl, methylsulfonyl, or methylmercapto) methylergolines, 8-ergolenes or 9-ergolenes, useful as prolactin inhibitors and in the treatment of Parkinsonism.