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CAS No. : | 214262-97-2 | MDL No. : | MFCD00800624 |
Formula : | C12H13FO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RLAKVCCLVVITLS-UHFFFAOYSA-N |
M.W : | 208.23 | Pubchem ID : | 736131 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
sulfuric acid;Heating / reflux; | To a solution of methyl [1- (3-FLUOROPHENYL) CYCLOPENTANECARBOXYLIC] acid [(5.] [0G,] 24.01 mmol) in anhydrous methanol was added 1 mL of concentrated sulfuric acid. The mixture was refluxed overnight. The mixture was neutralized to pH 4-5 with sodium carbonate. The solvent was evaporated. The residue was dissolved in ethyl acetate (50 mL), washed with brine (3 x 10 mL, dried over [MGS04.] The crude product was used for the next reaction without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 3; 4-[1-(3-fluorophenyl)cyclopentyl]-1,3-thiazol-2-amine; Step A; To a -70 C solution containing 1.04 g (5.00 mmol) of 1-(3-fluorophenyl)-1-cyclopentane carboxylic acid in 25 mL of ether was added 530 mg (5.24 mmol) of N-methylmorpholine and 716 mg (5.24 mmol) of isobutyl chloroformate. The reaction mixture was stirred for 1 h then filtered through a fine frit funnel. The filtrate was cooled to 0 C and excess CH2N2 (40 mL of diazomethane prepared from 50 mL ether/ 15 mL 40% KOH and 4.4 g MNNG) was pipetted into the flask containing the mixed anhydride. The resulting mixture was stirred until LCMS showed complete conversion to the diazoketone (14 h) then the excess CH2N2 was evaporated. The resulting yellow oil was dissolved in ether and cooled to 0 C and treated with 48% HBr (1.5 mL). Effervescence occurred within 10 seconds and LCMS detected complete conversion to a new peak after 1 h. The reaction mixture was diluted with 50 mL of ether and washed with saturated bicarbonate 2 x 10 mL, water (10 mL) and brine (10 mL). Evaporation of the solvent left the bromo ketone which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; | General procedure: A mixture of 1-[3,5-bis(trifluoromethyl)phenyl]cyclopentanecarboxylic acid (91.0 mg, 279 pmol),(rac)-5-phenyl-3,9-diazaspiro[5.5]undecan-2-one, salt with hydrochloric acid (102 mg, 363 mihoI, Intermediate 16), HATU (117 mg, 307 pmol) and N,N-diisopropylethylamine (240 mI, 1.4 mmol) in DMF (3.3 ml) was stirred over night at room temperature. For the work-up, water was added, the mixture was extracted with ethyl acetate and the combined organic phases were dried and concentrated. The residue was purified by preparative FIPLC (Method 6) to give the title compound 6.10 mg (4 % yield. |
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