1455091-10-7
FG-4592 interMediate
CAS: 1455091-10-7
Molecular Formula: C18H15NO4
1455091-10-7 - Names and Identifiers
1455091-10-7 - Physico-chemical Properties
| Molecular Formula | C18H15NO4 |
| Molar Mass | 298.77 |
| Density | 1.320±0.06 g/cm3(Predicted) |
| Boling Point | 534.7±45.0 °C(Predicted) |
| pKa | 5.80±0.50(Predicted) |
| Storage Condition | 2-8°C |
| Use | Uses Methyl 4-hydroxy-7-phenoxyisoquinoline-3-formate is an intermediate of N-[(4-hydroxy-1-methyl-7-phenoxy-3-isoquinolinyl) carbonyl] glycine (H948180), a hypoxia-inducible factor (HIF) proly hydroxylase inhibitor used to increase leukocyte levels in blood and bone marrow hematopoietic progenitors. |
1455091-10-7 - Upstream Downstream Industry
1455091-10-7 - Uses and synthesis methods
application
4-hydroxy-7-phenoxyisoquinoline-3-methyl formate can be used as an intermediate in pharmaceutical synthesis. It can be used as a raw material to prepare an intermediate 5-phenoxyisobenzofuran-1 (3H)-one, and further react to prepare 2-(chloromethyl)-4-phenoxybenzoate methyl ester, methyl 4-hydroxy-7-phenoxyisoquinoline-3-formate was prepared by reaction with N-p-toluenesulfonylglycine methyl ester.
Preparation
Step 1: 5-phenoxyisobenzofuran-1 (3H)-one
add phenol (20.4g,0.22mol) and DMF50mL to the reaction bottle, start stirring, add 5-bromoisobenzofuran-1 (3H)-one (34.0g,0.16mmol), acetylacetone (3.2g,0.03mol), cuprous bromide (3.6g,0.03mol), potassium carbonate (30.8g,0.22mol) at room temperature, and replace them with nitrogen for three times, heating to 90 ℃ and stirring for reaction overnight, adding 1000mL of purified water to the reaction solution, suction filtration, dissolving the filter cake with 800mL of dichloromethane, washing the organic phase with 800mL of 1N hydrochloric acid solution, washing with 1000mL of purified water, drying the organic phase, concentrating to dry under reduced pressure, adding methanol to 50mL for beating for 1 hour, suction filtration, and obtaining the title compound 5-phenoxyisobenzofuran.
The second step: 2-(chloromethyl)-4-phenoxybenzoate methyl
5-phenoxy isobenzofuran -1(3H)-one (1.0g,4.42mmol), xylene 10mL, benzyl triethylammonium chloride (300mg,1.32mmol), and boron trifluoride ether (200mg,1.41mmol) were sequentially added to the reaction bottle, heated to 100 ℃, dripped with sulfoxide (5.0g,42.03mmol), heated to 135 ℃ for 5 hours after dripping, after the thin layer chromatography monitors the reaction is complete, the filtrate is concentrated under reduced pressure, the concentrated solution is added with methanol 3mL, the reaction is stirred at 55 ℃ for 1 hour, the reduced pressure is concentrated to dry, the residual solution is added with ethyl acetate to dissolve, the organic phase is washed with potassium carbonate solution and sodium chloride solution, concentrated to dry, and the title compound (1.0g,83.0%) is obtained, which is directly used for the next reaction.
The third step: 4-hydroxy-7-phenoxyisoquinoline-3-methyl formate
add 2-(chloromethyl)-4-phenoxybenzoate methyl ester (0.68g,2.46mmol), N-p-toluenesulfonyl glycine methyl ester (0.7g,2.88mmol), potassium carbonate (0.68g,4.923mmol), potassium iodide (0.16g,0.96mmol) and DMF into the reaction bottle, replace with nitrogen, and heat to 50 ℃ for 1 hour, add 2mL of sodium methoxide methanol solution to room temperature and stir for 30min. After the reaction is completely monitored by thin layer chromatography, add 40mL of purified water to the reaction solution, add glacial acetic acid dropwise under stirring to adjust pH = 7, filter by suction, add 4mL of acetone to the filter cake, stir for 2 hours, filter by suction to obtain the title compound 4-hydroxy -7-phenoxyisoquinoline -3-methyl.
Last Update：2024-04-09 21:04:16
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View History
Raw Materials for 1455091-10-7
Methyl 2-(4-methylphenylsulfonamido)acetate
2-{[(methoxycarbonylmethyl)(toluene-4-sulfonyl)amino]methyl}-4-phenoxybenzoic acid methyl ester
5-Bromophthalide
2-{[(methoxycarbonylmethyl)(toluene-4-sulfonyl)amino]methyl}-4-phenoxybenzoic acid methyl ester
5-Bromophthalide
Downstream Products for 1455091-10-7