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

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

Safety Information

WGK Germany 

3

HS Code 

2933998090

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-(84378-44-9)Related Product Information

• Imidazolidinyl urea
• Levamisole
• Imidazole
• Methimazole
• Ro 15-3505
• N,N-Dimethyformamide diethy acetal
• 7-Fluoro-3,4-dihydro-4-methyl-1H-1,4-benzodiazepine-2,5-dione
• Ro 14-7437
• 4H-Imidazo[1,5-a][1,4]benzodiazepine-3-carboxylicacid, 5,6-dihydro-8-hydroxy-5-methyl-6-oxo-, ethyl ester
• fluMazenil iMpurity
• Flumazenil
• 4H-IMIDAZO[1,5-A][1,4]BENZODIAZEPINE-3-CARBOXYLIC ACID, 8-FLUORO-5,6-DIHYDRO-5-METHYL-6-OXO-
• 1-[2-(1H-IMIDAZOL-1-YL)PHENYL]METHANAMINE
• 3'-(2-FLUOROETHYL)FLUMAZENIL
• 2-AMINO-5-FLUOROBENZAMIDE
• 2-(1H-IMIDAZOL-1-YL)BENZENECARBOXAMIDE