| Identification | Back Directory | [Name]
4-AMINO-2-FLUORO-N-METHYLBENZAMIDE | [CAS]
915087-25-1 | [Synonyms]
Enzalutamide Impurity 20
4-AMINO-2-FLUORO-N-METHYLBENZAMIDE
N-Methyl-2-fluoro-4-aminobenzamide
N-Methyl-4-amino-2-fluoro-benzamide
4-amino-2-fluoro-N-menthylbenzamide
BenzaMide, 4-aMino-2-fluoro-N-Methyl-
2. 4-aMino-2-fluoro-N-MethylbenzaMide | [Molecular Formula]
C8H9FN2O | [MDL Number]
MFCD09909322 | [MOL File]
915087-25-1.mol | [Molecular Weight]
168.17 |
| Chemical Properties | Back Directory | [Melting point ]
160 - 163°C | [Boiling point ]
320℃ | [density ]
1.234 | [Fp ]
147℃ | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
14.12±0.46(Predicted) | [color ]
White to Off-White | [Stability:]
Moisture Sensitive | [InChI]
InChI=1S/C8H9FN2O/c1-11-8(12)6-3-2-5(10)4-7(6)9/h2-4H,10H2,1H3,(H,11,12) | [InChIKey]
XOKAXPQJUODMSH-UHFFFAOYSA-N | [SMILES]
C(NC)(=O)C1=CC=C(N)C=C1F |
| Hazard Information | Back Directory | [Description]
4-amino-2-fluoro-N-methylbenzamide is a novel antiandrogen drug MDV (Marek's Disease Virus) 3100 key intermediate which is the new generation oral androgen antagonist medicine of united states drug developer Medivation company exploitation, be mainly used in treating advanced prostate cancer (CRPC) patient. | [Uses]
4-?Amino-?2-?fluoro-?N-?methylbenzamide acts as a reagent in the design, synthesis and biological evaluation of novel 5-oxo-2-thioxoimidazolidine derivatives as potent androgen receptor antagonists. Also, in the preparation and structure-activity relationship of chiral benzyloxypyridinone derivatives as c-Met kinase inhibitors | [Preparation]
2-fluoro-4-nitrotoluene as raw material, through potassium permanganate oxidation, the thionyl chloride chlorination, methylamine amination, and Pd/C hydrogenation reduction prepare 4-amino-2-fluoro-N-methylbenzamide.
 | [Synthesis]
General procedure for the synthesis of N-methyl-2-fluoro-4-aminobenzamide from the compound (CAS: 956104-46-4): Trifluoroacetic acid (TFA, 1 mL) was slowly added dropwise to a solution of 4-methylamino-2-fluorobenzyl amide (60 mg, 0.21 mmol) in anhydrous dichloromethane (DCM, 0.5 mL), under protection of argon gas. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the solvent was removed by rotary evaporator and the residue was purified by silica gel fast column chromatography (eluent: hexane/ethyl acetate) to quantitatively obtain the target product, N-methyl-2-fluoro-4-aminobenzamide. The product structure was confirmed by 1H NMR (500 MHz, CDCl3) and 13C NMR (500 MHz, CDCl3): 1H NMR δ 2.98 (d, J = 4.8 Hz, 3H), 4.15 (br s, 2H), 6.32 (d, J = 14.3 Hz, 1H), 6.48 (d, J = 8.2 Hz, 1H), 6.61 ( br s, 1H), 7.90 (dd, J = 8.6 Hz, 1H); 13C NMR δ 26.63, 100.8 (d, J = 28.8 Hz), 110.3 (d, J = 244.6 Hz), 110.9, 133.3 (d, J = 4.3 Hz), 151.4 (d, J = 12.5 Hz), 162.2 (d, J = 244.6 Hz), 164.3 (d, J = 3.5 Hz). | [References]
[1] Patent: WO2008/119015, 2008, A2. Location in patent: Page/Page column 52-53
[2] Patent: US9388159, 2016, B2. Location in patent: Page/Page column 21; 22 |
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