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| | 4H-IMIDAZO[1,5-A][1,4]BENZODIAZEPINE-3-CARBOXYLIC ACID, 8-FLUORO-5,6-DIHYDRO-5-METHYL-6-OXO- Basic information |
| Product Name: | 4H-IMIDAZO[1,5-A][1,4]BENZODIAZEPINE-3-CARBOXYLIC ACID, 8-FLUORO-5,6-DIHYDRO-5-METHYL-6-OXO- | | Synonyms: | FluMazenil Carboxylic Acid;4H-IMIDAZO[1,5-A][1,4]BENZODIAZEPINE-3-CARBOXYLIC ACID, 8-FLUORO-5,6-DIHYDRO-5-METHYL-6-OXO-;FLUMAZENIL ACID;3-Desethyl-FMZ;4H-Imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid,;8-fluoro-5,6-dihydro-5-methyl-6-oxo-;8-Fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid;8-Fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid | | CAS: | 84378-44-9 | | MF: | C13H10FN3O3 | | MW: | 275.24 | | EINECS: | | | Product Categories: | | | Mol File: | 84378-44-9.mol | ![4H-IMIDAZO[1,5-A][1,4]BENZODIAZEPINE-3-CARBOXYLIC ACID, 8-FLUORO-5,6-DIHYDRO-5-METHYL-6-OXO- Structure](CAS/GIF/84378-44-9.gif) |
| | 4H-IMIDAZO[1,5-A][1,4]BENZODIAZEPINE-3-CARBOXYLIC ACID, 8-FLUORO-5,6-DIHYDRO-5-METHYL-6-OXO- Chemical Properties |
| Melting point | >255°C (Subl.) | | Boiling point | 570.5±50.0 °C(Predicted) | | density | 1.55±0.1 g/cm3(Predicted) | | storage temp. | Sealed in dry,Store in freezer, under -20°C | | solubility | DMSO (Slightly), Methanol (Slightly, Heated) | | form | Solid | | pka | 4.31±0.20(Predicted) | | color | White to Off-White | | Major Application | pharmaceutical (small molecule) | | InChI | InChI=1S/C13H10FN3O3/c1-16-5-10-11(13(19)20)15-6-17(10)9-3-2-7(14)4-8(9)12(16)18/h2-4,6H,5H2,1H3,(H,19,20) | | InChIKey | SFVXVWJBSJCRJO-UHFFFAOYSA-N | | SMILES | N12C=NC(C(O)=O)=C1CN(C)C(=O)C1=CC(F)=CC=C12 |
| WGK Germany | 3 | | HS Code | 2933998090 | | Storage Class | 11 - Combustible Solids |
| | 4H-IMIDAZO[1,5-A][1,4]BENZODIAZEPINE-3-CARBOXYLIC ACID, 8-FLUORO-5,6-DIHYDRO-5-METHYL-6-OXO- Usage And Synthesis |
| Chemical Properties | Colorless solid | | Uses | Flumazenil carboxylic acid is a derivative of Flumazenil (F500450), a benzodiazepine antagonist that can prevent or abolish (at the receptor level) the effects of a benzodiazepine. | | Synthesis | The general procedure for the synthesis of 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[F]imidazo[1,5-a][1,4]diazepine-3-carboxylic acid from ethyl 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate is as follows: 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[1,5-a][1,4]diazepine-3-carboxylic acid was prepared from 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[1,5-a][1,4]diazepine-3-carboxylic acid as follows. -6-oxo-5,6-dihydro-4H-benzo[F]imidazo[1,5-a][1,4]diazepine-3-carboxylic acid ethyl ester (0.5 g, 1.7 mmol) was suspended in tetrahydrofuran (THF, 50 mL). Aqueous sodium hydroxide (2M, 10 mL) was added to the suspension to completely dissolve the solid. The reaction mixture was stirred at room temperature until completion of the reaction was confirmed by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the solvent was evaporated under reduced pressure. The residue was dissolved in water and acidified with 2M hydrochloric acid to precipitate the target product as a solid. The solid product was collected by filtration and dried under vacuum to afford 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylic acid as a colorless solid (0.45 g, 100% yield). The structure of the product was confirmed by 1H NMR (CD3OD): δ 3.24 (3H, s, CH3), 4.62 (1H, br d, J = 15.4 Hz, CHaHb), 5.19 (1H, br d, J = 15.4 Hz, CHaHb), 7.62 (1H, ddd, JHF = 12.5 Hz, JHH = 7.7 and 3.1 Hz. CFCHCH), 7.79 (1H, dd, JHF = 8.9 Hz, JHH = 3.1 Hz, CCHCF), 7.87 (1H, dd, JHF = 9.1 Hz, JHH = 4.5 Hz, CHCHCF), 9.63 (1H, s, NCHN). | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 3, p. 821 - 826
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S517-S519 |
| | 4H-IMIDAZO[1,5-A][1,4]BENZODIAZEPINE-3-CARBOXYLIC ACID, 8-FLUORO-5,6-DIHYDRO-5-METHYL-6-OXO- Preparation Products And Raw materials |
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