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CAS No. : | 57931-81-4 | MDL No. : | |
Formula : | C11H9NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 219.19 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
89% | With hydrogenchloride for 5h; Heating; | |
56.2% | With hydrogenchloride In acetic acid at 60℃; for 10h; Reflux; | 4.1.3. General procedure B for the synthesis of compounds c1-c3 General procedure: At first, the concentrated HCl (1.38 mL, 37%) was slowly added tothe acetic anhydride (4.50 mL) at 0 C, which yielded a solution ofapproximately 2.8 M HCl in acetic acid. Subsequently, the preparedsolution (3 mL) of 2.8 M HCl in acetic acid was added to the ester(b1-b3, 1.00 mmol). The reaction mixture was heated to 60 C andrefluxed at that temperature for 10 h. After the reaction mixturewas cooled down to the room temperature, it was mixed with 2-propanol. The end product was obtained by filtering, washedwith 2-propanol and dried in a vacuum. 4.1.3.1. 4-Hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (c1). Yield 56.2%, white solid. ESI-MS (m/z): 218.41[MH]. 1H NMR (500 MHz, DMSO-d6) δ 14.42 (s, 1H), 11.34 (s, 1H),8.19 (d, J 7.9 Hz, 1H), 7.99-7.95 (m, 1H), 7.82 (d, J 8.7 Hz, 1H), 7.55(t, J 7.6 Hz, 1H), 3.74 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With dicyclohexyl-carbodiimide In toluene at 80 - 85℃; for 2h; Large scale; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14.1% | Stage #1: 1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: 2-amino-5-ethyl-1,3,4-thiadiazole In N,N-dimethyl-formamide at 20℃; for 48h; | 4.1.5. General procedure D for the synthesis of compounds g1-g37 General procedure: EDCI (1.5 equiv) was added to a solution of the acid (c1-c3, 1.1equiv), DIPEA (1.5 equiv) and HOBt (1.5 equiv) in DMF (10 mL) at0 C and stirred for 5 min. Then, the amine (f1-f35, 1.0 equiv) wasadded to the solution and the reaction mixture was stirred for48 h at room temperature. The mixture was poured into the icedwater. The precipitated solid was filtered and washed with icedwater. After the purification by a silica gel column chromatography,the target compound (11 or g1-g37) was produced. 4.1.5.1. 1-methyl-N-(5-ethyl-1,3,4-thiadiazol-2-yl)-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamide (11). Yield 14.1%, light yellowsolid. ESI-MS (m/z): 331.11[MH]. 1H NMR (400 MHz, DMSO-d6)δ 8.28-8.23 (m, 0H), 7.87-7.84 (m, 1H), 7.74-7.69 (m, 1H), 7.51-7.44(m, 1H), 7.32 (dd, J 16.5, 8.5 Hz, 1H), 3.60 (s, 3H), 1.29-1.17 (m, 2H),0.98-0.85 (m, 3H). 13C NMR (100 MHz, DMSO-d6) δ 162.77, 161.79,161.38, 143.29, 140.25, 133.39, 130.37, 123.04, 120.84, 115.87, 109.55,98.89, 36.24, 29.68, 14.14. HRMS calcd for C15H15N4O3S [MH],331.0865; found, 331.0859. |