6-Hydroxy-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one
Olodaterol
CAS: 868049-49-4
Molecular Formula: C21H26N2O5
6-Hydroxy-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one - Names and Identifiers
6-Hydroxy-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one - Physico-chemical Properties
| Molecular Formula | C21H26N2O5 |
| Molar Mass | 386.44 |
| Density | 1.250 |
| Boling Point | 649.0±55.0 °C(Predicted) |
| pKa | 9.42±0.20(Predicted) |
| Use | Odarterol has a nearly full-effect β2-receptor agonism (the semi-maximum effect concentration is 0.1nM, and the affinity internal activity with isoprenaline is 88%). Otarterol has different effects on different β-adrenergic receptors. It has a complete agonist effect on β2-receptors, while it is a partial agonist to β1-adrenergic receptors. |
6-Hydroxy-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one - Upstream Downstream Industry
6-Hydroxy-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one - Introduction
Odarterol (Olodaterol) is a new type of selective fast-acting β2-adrenergic receptor agonist. This product can bind to β2 receptors to increase the level of intracellular cAMP, which in turn causes protein kinase A The activation and phosphorylation of other related targets finally achieve the effect of dilating the trachea. Odarol has high selectivity for β2-adrenergic receptors (referred to as β2-receptors) and has rapid onset of effect, long half-life, more than 12h, can maintain 24h of bronchodilation.
Last Update：2024-04-10 22:29:15
6-Hydroxy-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one - Synthesis method
Synthesis method of odaterol:
- 2, 5-dihydroxyacetophenone (
- Reaction with benzyl bromide to obtain 1-[2-hydroxy-5-(benzyloxy)-phenyl] ethanone
- After nitration, it is reduced to 1-[2-hydroxy-3-amino-5-(benzyloxy) phenyl]-ethanone under the action of platinum dioxide
- 6-benzyloxy-8-(2-bromoacetyl)-2H-benzo [B][1,4]-oxazine -3(4H)-one is obtained by acyl chlorination reaction, intramolecular condensation and bromination reaction
- (R)-6-benzyloxy-8-(ethylene oxide -2-yl)-2H-benzo [B][1,4] oxazine -3(4H)-one obtained by asymmetric reduction and intramolecular ring
- Condensation with 1-(4-methoxyphenyl)-2-methyl-2-propylamine (9) to obtain 6-benzyloxy-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1, 1-dimethylethyl] amino] ethyl]-2H-benzo [B][1,4] oxazine -3(4H)-one
- re-debenzyl protection 1, the total yield 16.2% (in 2).
platinum dioxide used in this method is more expensive, and the bromination reaction yield is low (74%). Compound 2 is protected by benzylation, nitration, nitro reduction, acyl chlorination, intramolecular condensation, oxidation, esterification, condensation and debenzyl. The target product obtained by this method is the racemate of Odarterol, which is not a single configuration target product.
Last Update：2024-04-09 21:01:54
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Product Name: 6-Hydroxy-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one Visit Supplier Webpage Request for quotationCAS: 868049-49-4
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View History
6-Hydroxy-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one
Chrysodine
Solvent Black 29
1187830-75-6
152955-55-0
4-Chloro-2-fluoro-5-sulfonamidebenzonitrile
2-mercapto-1,3,4-thiadiazol
185672-33-7
545347-75-9
1-Pentyl-4-amino-N,N-di(2-propenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
Chrysodine
Solvent Black 29
1187830-75-6
152955-55-0
4-Chloro-2-fluoro-5-sulfonamidebenzonitrile
2-mercapto-1,3,4-thiadiazol
185672-33-7
545347-75-9
1-Pentyl-4-amino-N,N-di(2-propenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide
Raw Materials for 6-Hydroxy-8-[(1R)-1-hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-2H-1,4-benzoxazin-3(4H)-one
8-[(1R)-1-Hydroxy-2-[[2-(4-methoxyphenyl)-1,1-dimethylethyl]amino]ethyl]-6-(phenylmethoxy)-2H-1,4-benzoxazin-3(4H)-one
6-benzyloxy-8-((R)-2-chloro-1-hydroxy-ethyl)-4H-benzo[1,4]-oxazin-3-one
6-benzyloxy-8-((R)-2-chloro-1-hydroxy-ethyl)-4H-benzo[1,4]-oxazin-3-one