Structure of 74647-39-5
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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. : | 74647-39-5 |
Formula : | C11H8N2O2 |
M.W : | 200.19 |
SMILES Code : | O=C(C1=NC=CC(C2=CC=CC=C2)=N1)O |
MDL No. : | MFCD16988171 |
InChI Key : | OKGSNIRNGQVKJO-UHFFFAOYSA-N |
Pubchem ID : | 12582974 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-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 |
---|---|---|
87% | With sulfuric acid; at 100℃; | General procedure: A mixture of an appropriate 4-substititedphenylpyrimidine-2-carboxamide (0.025mol) and 20% H2SO4 (100mL) was heated at 100C for 5-10h and monitored by TLC. The reaction mixture was poured onto ice/water with vigorously stirring and then the precipitatewas collected by filtration and dried to give the corresponding 4-substititedphenylpyrimidine-2-carboxylic acids as light yellow solids. |
86% | With sulfuric acid; at 100℃; for 10.0h; | A mixture of intermediate c (5 g, 0.06 mol)Was added to 20% sulfuric acid (100 mL)100 C for 10 hours,After the completion of the reaction, the temperature was lowered to room temperature,Add 200 mL of water,Stirring for half an hour,Take filter cake, dry,To give a pale yellow solid, 4.3 g,Yield 86%. |
47% | With ethanol; sodium hydroxide; at 100℃; | A solution of 2-cyano-4-phenylpyrimidine and 4-phenylpyrimidine-2-carboxamide (18?, 0.42 g, 2.4 mmol) in a 1 : 1 mixture of EtOH and NaOH solution (1 N) was allowed to stir at 100 C for 3 h. The resulting reaction mixture ws concentrated, water (20 mL) was added and the basic aqueous solution was acidified to pH 6 with concentrated HC1 to give 200 mg (47%) of 4-phenylpyrimidine-2-carboxylic acid (19?) as a yellow solid. NMR (CD3OD, 400 MHz) d 8.81 (br s, 1H), 8.38 (d, J= 6.7 Hz, 2H), 8 21 (br s, i l l). 7.68 - 7.22 (m, 3H). MS m/e: 201 ( I · 1 1 ) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride;Reflux; | <strong>[74647-39-5]4-phenylpyrimidine-2-carboxylic acid</strong> (0.01 mol)Dissolved in 15 mL of thionyl chloride,Reflux reaction 5-7h, evaporated to dryness,The obtained solid was vacuum-dried and stored,To give the intermediate 4-phenylpyrimidine-2-carbonyl chloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | 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℃; | To a solution of 5-((6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yl)oxy)pyridin- 2-amine (S?, 50 mg, 0.12 mmol), <strong>[74647-39-5]4-phenylpyrimidine-2-carboxylic acid</strong> (19?, 35 mg, 0.17 mmol) in DMF (1 mL), DIEA (100 pL, 74 mg, 0.57 mmol) and HATU (140 mg, 0.37 mmol) were added. The reaction mixture was then allowed to stir at room temperature overnight, but a significant amount of the starting material 2-aminopyridine 5? was detected. Additional equivalents of reagents wre added and the reaction mixture was allowed to stir at room temperature until most of the starting 2-aminopyridine 5? was consumed. The reaction mixture was then diluted with water (20 ml) and extracted with DCM (3 x 10 mL) and the combined organic layer was dried (MgS()4) and concentrated to give a brown residue. Reverse phase chromatography provided 26 mg (36%) ofAr-(5-((6-methoxy-7-(3-morpholinopropoxy)quinolin- 4-yl)oxy)pyridin-2-yl)-4-phenylpyrimidine-2-carboxamide (4) as a white solid. NMR (CDJOD, 300 MHz) d 9.03 (d, J= 5.4 Hz, 1H), 8.72 (d, J = 6.7 Hz, 1H), 8.67 (dd, J= 9.1, 0.7 Hz, 1H), 8.52 (dd, J= 2.9, 0.7 Hz, 1H), 8.40 - 8.30 (m, 2H), 8.20 (d, J= 5.4 Hz, 1H), 7.99 (dd, J = 9.1, 2.9 Hz, i l l). 7.86 (s, 1H), 7.66 - 7.52 (m, 4H), 7.06 (d, J = 6.7 Hz, 1H), 4.43 (t, J= 5.5 Hz, 2H), 4.19 - 4 03 (br s, 21 1). 4.09 (s, 3H), 3.93 - 3.75 (m, 2H), 3.67 (d, J= 12.5 Hz, 2H), 3 49 (t, ./= 7 4 Hz, 2H), 3.28 - 3.13 (m, 2H), 2 45 (p, ,/= 6.4 Hz, 2H) MS m/e: 593 (M+H)7 |
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