Structure of 406204-74-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 406204-74-8 |
Formula : | C9H4Cl2FN |
M.W : | 216.04 |
SMILES Code : | FC1=CC=C2N=C(Cl)C=C(Cl)C2=C1 |
MDL No. : | MFCD09261383 |
InChI Key : | XLEGVSYSXNPSAU-UHFFFAOYSA-N |
Pubchem ID : | 27282142 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In methanol; at 20℃; for 2h;Heating / reflux; | b) 2-Chloro-6-fluoro-4-methoxy-quinoline; To <strong>[406204-74-8]2,4-dichloro-6-fluoro-quinoline</strong> (3.3 g, 15 mmol) in MeOH (50 mL) was added NaOMe (2.5 g, 46 mmol) at rt. under an atmosphere of nitrogen. The slurry was heated at reflux for 2 h, cooled to rt. and concentrated. The residue was purified by flash chromatography [60 g Si02, 4 x 12 cm column, eluting with DCM], which afforded 2.17 g (69%) of the title compound as a white solid material. 'H NMR (300.1 MHz, CDC) 5 7.89 (dd, 1H), 7.68 (dd, 1H), 7.43 (ddd, 1H), 6.71 (s, 1H), 4.02 (s, 3H). LC-MS [M+H] + 212 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | a) 2, 4-Dichloro-6-fluoro-quinoline; To a mixture of 4-fluoroaniline (8.5 g, 76.5 mmol) and malonic acid (8.0 g, 76.9 mmol) was added POC13 (160 g, 1.04 mol) and the mixture was slowly heated to 100C and then kept at this temperature for 18 h. The reaction mixture was cooled to room temperature and poured into ice-water (1.0 L). The brown slurry was filtered and the solid brown/orange material was purified by flash chromatography [350 g Si02, 6 x 24 cm column, eluting with DCM], which afforded 3.37 g (20%) of the title compound as an off-white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; | General procedure: A mixture of substituted 2,4-dichloroquinolines 2a-j (1mol), powdered K2CO3 (1.2 mol) and 4-(3-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate(1; 1 mol) in DMF was stirred at 70 C for 48 h.The progress of the reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was poured into a beaker containing ice cold water and stirred well, the separated solid filtered to dryness and purified through column chromatography of silica gel (60-120 mesh)using pet. ether and ethyl acetate (7:3) mixture as eluent,which afforded the products 3a-j in pure form. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With triethylamine; In 1-methyl-pyrrolidin-2-one; at 100℃; for 1h;Microwave irradiation; | 2,4-Dichloro-6-fluoroquinoline (200.0 mg, 0.93 mmol), 2-(4-nitrophenyl)ethan-1-amine hydrochloride (188.0 mg, 0.93 mmol) and Et3N (390.0 muL, 2.79 mmol) were added to NMP (3.1 mL). The reaction mixture was reacted in a microwaver (50W, 100) for 1 hour and cooled to room temperature. After addition of ice water, the reaction mixture was extracted with CH2Cl2. The organic layer was washed with brine, dried with Na2SO4and filtered. The residue obtained under reduced pressure was purified by column chromatography (n-Hex:EtOAc=1:1) on silica. The fractions containing the product were collected and evaporated to obtain the white solid compound, 2-chloro-6-fluoro-N-(4-nitrophenethyl)quinolin-4-amine (45.0 mg, 14%).[299][300]1H NMR (300 MHz, CDCl3) delta = 8.27 - 8.17 (m, 2H), 7.96 - 7.86 (m, 1H), 7.49 - 7.36 (m, 3H), 7.17 (dd,J= 2.7, 9.5 Hz, 1H), 6.49 (s, 1H), 4.91 (t,J= 4.8 Hz, 1H), 3.73 - 3.63 (m, 2H), 3.19 (t,J= 7.1 Hz, 2H)[301]LC/MS ESI (+): 346 (M+1) |