(6aR,9S)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

Base Information

• Chemical Name: (6aR,9S)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• CAS No.: 65700-36-9
• Molecular Formula: C₃₂H₄₀BrN₅O₅
• Molecular Weight: 654.604
• European Community (EC) Number: 806-443-3
• DSSTox Substance ID: DTXSID30525872
• Mol file: 65700-36-9.mol

Synonyms:65700-36-9;(6aR,9S)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;DTXSID30525872;(8S)-2-Bromo-alpha-Ergocryptine;(5'alpha,8alpha)-2-Bromo-12'-hydroxy-5'-(2-methylpropyl)-3',6',18-trioxo-2'-(propan-2-yl)ergotaman

Chemical Property of (6aR,9S)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

Chemical Property:

• Boiling Point: 891.3±65.0 °C(Predicted)
• PKA: 9.60±0.60(Predicted)
• Density: 1.52±0.1 g/cm3(Predicted)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 653.22128
• Heavy Atom Count: 43
• Complexity: 1230

Purity/Quality:

97% ^*data from raw suppliers

(8S)-2-Bromo-α-Ergocryptine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1C(=O)N2CCCC2C3(N1C(=O)C(O3)(C(C)C)NC(=O)C4CN(C5CC6=C(NC7=CC=CC(=C67)C5=C4)Br)C)O
• Isomeric SMILES: CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]3(N1C(=O)[C@](O3)(C(C)C)NC(=O)[C@@H]4CN([C@@H]5CC6=C(NC7=CC=CC(=C67)C5=C4)Br)C)O
• Uses: The (8S)-epimer of 2-Bromo-α-Ergocryptine (B682600), as impurity. Dopamine receptor agonist; derivative of the ergotoxin group of ergot alkaloids. Prolactin inhibitor; antiparkinsonian.

Technology Process of (6aR,9S)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

There total 3 articles about (6aR,9S)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.2%

α-ergocryptine (511-09-1,511-10-4,106188-95-8) → Bromocriptine (25614-03-3,65700-36-9,68944-89-8,82773-21-5,82796-58-5)

Guidance literature:

With piperidone-⁽²⁾-hydrotribromide; In 1,4-dioxane; for 0.0333333h; Ambient temperature;

Reference yield: 70.0%

α-ergocryptine (511-09-1,511-10-4,106188-95-8) → 2-bromo-α-ergocryptine (25614-03-3,65700-36-9,68944-89-8,82773-21-5,82796-58-5)

Guidance literature:

With boron trifluoride diethyl etherate; bromine; In tetrahydrofuran; dichloromethane; at -20 ℃; for 0.0166667h;

DOI:10.1135/cccc19920565

Reference yield:

α-ergocryptine (511-09-1,511-10-4,106188-95-8) + piperidone-(2)-hydrotribromide → piperidin-2-one (675-20-7) + Bromocriptine (25614-03-3,65700-36-9,68944-89-8,82773-21-5,82796-58-5)

Guidance literature:

In 1,4-dioxane; for 0.0333333h; Product distribution; Ambient temperature; bromination reagent; var. ergot alkaloids;

upstream raw materials:

α-ergocryptine

α-ergocryptine

Refernces

• 1、 Rucman,Korsic,Jurgec. "A new synthesis of 2-bromo-α-ergocryptine and related ergot derivatives". . p. 406 - 410. Retrieved 2007/10/02.