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CAS No. : | 19541-96-9 | MDL No. : | MFCD02708434 |
Formula : | C9H10N4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 174.20 | 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 |
---|---|---|
81% | With potassium carbonate; acetic acid; In N,N-dimethyl-formamide; | Reference Example 2-43 4,5-Difluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid Under an argon atmosphere, a solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (6.01 g, 34.5 mmol), 2-chloro-4,5-difluorobenzoic acid (6.64 g, 34.5 mmol), copper acetate (II) (0.718 g, 3.95 mmol) and potassium carbonate (4.77 g, 34.5 mmol) in N,N-dimethylformamide (30 mL) was heated under reflux for 2 hours. The solution was cooled to room temperature, and poured into water. The solution was made weakly acidic by the addition of acetic acid, and the resulting crude crystals were collected by filtration. The crystals were washed with water and air dried to give the title compound (9.21 g, 81% yield). mp: 247-248 C. (recrystallized from methanol). NMR (DMSO-d6) delta: 2.25 (3H, s), 6.33 (1H, s), 7.28-7.34 (1H, m), 7.46-7.56 (1H, m), 7.80-8.02 (3H, m), 8.30-8.44 (1H, m), 12.30 (1H, br s), hidden (1H). |
81% | With potassium carbonate; acetic acid; In N,N-dimethyl-formamide; | Production Example 7 4,5-Difluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid Under an argon atmosphere, a solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (6.01 g, 34.5 mmol), 2-chloro-4,5-difluorobenzoic acid (6.64 g, 34.5 mmol), copper acetate (II) (0.718 g, 3.95 mmol) and potassium carbonate (4.77 g, 34.5 mmol) in N,N-dimethylformamide (30 mL) was heated under reflux for 2 hrs. The solution was cooled to room temperature, and poured into water. The solution was made weakly acidic by the addition of an acetic acid solution, and the resulting crude crystals were collected by filtration. The crystals were washed with water and air dried to give the title compound (9.21 g, 81% yield). mp: 247-248C (recrystallized from methanol). NMR (DMSO-d6) delta: 2.25 (3H, s), 6.33 (1H, s), 7.28-7.34 (1H, m), 7.46-7.56 (1H, m), 7.80-8.02 (3H, m), 8.30-8.44 (1H, m), 12.30 (1H, br s), hidden (1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | EXAMPLE 2-78 4-Chloro-5-fluoro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline Following the procedures described in Reference Example 2-5 and Example 2-1, the title compound was prepared from <strong>[111771-08-5]2-fluoro-6-iodobenzoic acid</strong> and 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (51% yield). mp: 160-161 C. (recrystallized from ethyl acetate). NMR (CDCl3) delta: 3.01 (3H, s), 7.14-7.29 (2H, m), 7.63-7.76 (1H, m), 7.88-8.01 (2H, m), 8.65-8.78 (2H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium carbonate; acetic acid; In N,N-dimethyl-formamide; | Reference Example 2-10 2-[[3-Methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]-5-(trifluoromethyl)benzoic acid A solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (8.71 g, 50.0 mmol), <strong>[657-06-7]2-chloro-5-(trifluoromethyl)benzoic acid</strong> (12.4 g, 55.0 mmol), copper acetate (II) (1.00 g, 5.50 mmol) and potassium carbonate (7.60 g, 55.0 mmol) in N,N-dimethylformamide (50 mL) was heated under reflux for 1.5 hours under an argon atmosphere. The solution was cooled to room temperature, and poured into water. The solution was made acidic by the addition of acetic acid, and the resulting crude crystals were collected by filtration. The crystals were washed with water and air dried to give the title compound (17.7 g, 89% yield). mp: 228-229 C. (recrystallized from ethyl acetate). NMR (CDCl3) delta: 2.37 (3H, s), 6.19 (1H, s), 7.13 (1H, ddd, J=1.0 Hz, 4.8 Hz, 7.4 Hz), 7.70-7.85 (3H, m), 7.93 (1H, d, J=8.4 Hz), 8.39 (1H, d, J=1.8 Hz), 8.45 (1H, ddd, J=0.8 Hz, 1.8 Hz, 4.8 Hz), 12.46 (1H, br s), hidden (1H). |
89% | With potassium carbonate; acetic acid; In N,N-dimethyl-formamide; | Production Example 4 2-[[3-Methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]-5-(trifluoromethyl)benzoic acid A solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (8.71 g, 50.0 mmol), <strong>[657-06-7]2-chloro-5-(trifluoromethyl)benzoic acid</strong> (12.4 g, 55.0 mmol), copper acetate (II) (1.00 g, 5.50 mmol) and potassium carbonate (7.60 g, 55.0 mmol) in N,N-dimethylformamide (50 mL) was heated at reflux for 1.5 hrs. under an argon atmosphere. The solution was cooled to room temperature, and poured into water. The solution was made acidic by the addition of an acetic acid solution, and the resulting crude crystals were collected by filtration. The crystals were washed with water and air dried to give the title compound (17.7 g, 89% yield). mp: 228-229C (recrystallized from ethyl acetate). NMR (CDCl3) delta: 2.37 (3H, s), 6.19 (1H, s), 7.13 (1H, ddd, J=1.0Hz, 4.8Hz, 7.4Hz), 7.70-7.85 (3H, m), 7.93 (1H, d, J=8.4Hz), 8.39 (1H, d, J=1.8Hz), 8.45 (1H, ddd, J=0.8Hz, 1.8Hz, 4.8Hz), 12.46 (1H, br s), hidden (1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Reference Example 2-26 4,5-Dichloro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid Following the procedure described in Reference Example 2-5, the title compound was prepared from <strong>[50-82-8]2,4,5-trichlorobenzoic acid</strong> and 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (92% yield). mp: 288-289 C. (recrystallized from ethanol). NMR (DMSO-d6) delta: 2.26 (3H, s), 6.32 (1H, s), 7.29-7.35 (1H, m), 7.69 (1H, s), 7.83 (1H, d, J=8.4 Hz), 7,94-8.03 (2H, m), 8.41-8.44 (1H, m), 12.34 (1H, br s), hidden (1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate; acetic acid; In N,N-dimethyl-formamide; | Reference Example 2-5 2-[[3-Methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid A solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (5.23 g, 30 mmol), o-iodobenzoic acid (8.93 g, 36 mmol), copper acetate (II) (0.654 g, 3.6 mmol) and potassium carbonate (4.98 g, 36 mmol) in N,N-dimethylformamide (30 mL) was heated under reflux for 1 hour under an argon atmosphere. After the solution was cooled to room temperature, the mixture was poured into water. The solution was made weakly acidic by the addition of acetic acid, and the resulting crude crystals were collected by filtration. The crystals were washed with water and air dried to give the title compound (8.64 g, 98% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | With potassium carbonate; acetic acid; In N,N-dimethyl-formamide; | Reference Example 2-41 Methyl 2,3-difluoro-6-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoate A solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (6.16 g, 35.4 mmol), methyl 6-bromo-2,3-difluorobenzoate (8.11 g, 32.3 mmol), copper acetate (II) (0.49 g, 2.7 mmol) and potassium carbonate (4.46 g, 323 mmol) in N,N-dimethylformamide (30 mL) was heated under reflux for 1 hour under an argon atmosphere, and the solution was allowed to cool to room temperature and poured into water. The solution was made weakly acidic by the addition of acetic acid, and organic matter was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1) to give the title compound (0.86 g, 8% yield). NMR (CDCl3) delta: 2.30 (3H, s), 4.00 (3H, s), 5.94 (1H, s), 7.11-7.27 (2H, m), 7.23 (1H, dd, J=8.2 Hz, 9.2 Hz), 7.80 (1H, ddd, J=1.8 Hz, 7.4 Hz, 8.4 Hz), 7.94 (1H, ddd, J=1.0 Hz, 1.2 Hz, 8.4 Hz), 8.50 (1H, ddd, J=1.0 Hz, 1.8 Hz, 5.0 Hz), 11.60 (1H, br s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | EXAMPLE 1-52 4-Chloro-6-fluoro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline Following the procedures described in Reference Example 1-11 and Example 1-34, the title compound was prepared from <strong>[52548-63-7]5-fluoro-2-iodobenzoic acid</strong> and 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (57% yield). mp: 185-187 C. (recrystallized from ethyl acetate). NMR (DMSO-d6) delta: 3.00 (3H, s), 7.21-7.28 (1H, m), 7.62 (1H, ddd, J=3.0 Hz, 5.4 Hz, 9.4 Hz), 7.89-7.99 (2H, m), 8.19 (1H, dd, J=5.4 Hz, 9.4 Hz), 8.69 (1H, d, J=3.6 Hz), 8.77 (1H, d, J=8.2 Hz). | |
57% | EXAMPLE 2-80 4-Chloro-6-fluoro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline Following the procedures described in Reference Example 2-5 and Example 2-1, the title compound was prepared from <strong>[52548-63-7]5-fluoro-2-iodobenzoic acid</strong> and 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (57% yield). mp: 185-187 C. (recrystallized from ethyl acetate). NMR (DMSO-d6) delta: 3.00 (3H, s), 7.21-7.28 (1H, m), 7.62 (1H, ddd, J=3.0 Hz, 5.4 Hz, 9.4 Hz), 7.89-7.99 (2H, m), 8.19 (1H, dd, J=5.4 Hz, 9.4 Hz), 8.69 (1H, d, J=3.6 Hz), 8.77 (1H, d, J=8.2 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 99% 2: 14% | In tetrahydrofuran; methanol; sodium hydroxide; trichlorophosphate | 2.63 Methyl 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline-6-carboxylate EXAMPLE 2-63 Methyl 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline-6-carboxylate Following the procedure described in Reference Example 2-5, 4-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]isophthalic acid was prepared from bromoisophthalic acid and 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (99% yield). A solution of the compound (23.0 g, 68.0 mmol) in phosphorus oxychloride (108 g, 704 mmol) was heated under reflux for I hour. The reaction solution was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. To a stirred mixture of the residue in tetrahydrofuran (100 mL), methanol (10 mL) was added dropwise carefully, and the precipitate was collected by filtration. The precipitate was dissolved in a sodium hydroxide solution, and organic matter was extracted with chloroform. The extract was washed with saturated brine and water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform) to give the title compound (3.40 g, 14% yield). mp: 199-200° C. (recrystallized from ethyl acetate). NMR (CDCl3) δ: 3.01 (3H, s), 4.04 (3H, s), 7.27 (1H, ddd, J=1.0 Hz, 4.8 Hz, 7.4 Hz), 7.95 (1H, ddd, J=1.8 Hz, 7.4 Hz, 8.4 Hz), 8.19 (1H, d, J=9.0 Hz), 8.38 (1H, dd, J=1.8 Hz, 9.0 Hz), 8.69 (1H, ddd, J=0.8 Hz, 1.8 Hz, 4.8 Hz), 8.78 (1H, ddd, J=0.8 Hz, 1.0 Hz, 8.4 Hz), 9.15 (1H, d, J=1.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | Reference Example 2-22 6-Chloro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid Following the procedure described in Reference Example 2-5, the title compound was prepared from <strong>[13420-63-8]2-chloro-6-iodobenzoic acid</strong> and 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (28% yield). mp: 201-202 C. (recrystallized from ethanol). NMR (DMSO-d6) delta: 2.22 (3H, s), 6.12 (1H, s), 7.10 (1H, dd, J=1.0 Hz, 7.8 Hz), 7.32 (1H, ddd, J=1.0 Hz, 5.0 Hz, 7.0 Hz), 7.41 (1H, dd, J=7.4 Hz, 7.8 Hz), 7.52 (1H, dd, J=1.0 Hz, 8.4 Hz), 7.88 (1H, dd, J=1.0 Hz, 7.4 Hz), 8.01 (1H, ddd, J=1.8 Hz, 7.0 Hz, 8.4 Hz), 8.42 (1H, ddd, J=0.8 Hz, 1.8 Hz, 5.0 Hz), 11.35 (1H, br s), hidden (1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | EXAMPLE 2-84 4-Chloro-8-fluoro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline Following the procedures described in Reference Example 2-5 and Example 2-1, the title compound was prepared from <strong>[387-48-4]3-fluoro-2-iodobenzoic acid</strong> and 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (36% yield). mp: 191 C. (recrystallized from ethyl acetate). NMR (CDCl3) delta: 3.01 (3H, s), 7.26 (1H, ddd, J=1.2 Hz, 4.8 Hz, 7.4 Hz), 7.45-7.59 (2H, m), 7.97 (1H, ddd, J=1.2 Hz, 7.4 Hz, 8.4 Hz), 8.15-8.23 (1H, m), 8.68 (1H, ddd, J=0.8 Hz, 1.8 Hz, 4.8 Hz), 8.92 (1H, ddd, J=0.8 Hz, 1.2 Hz, 8.4 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Reference Example 2-34 4-Fluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid Following the procedure described in Reference Example 2-5, the title compound was prepared from <strong>[56096-89-0]4-fluoro-2-iodobenzoic acid</strong> and 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (86% yield). mp: 242-243 C. (recrystallized from ethanol). NMR (DMSO-d6) delta: 2.26 (3H, s), 6.35 (1H, s), 6.74 (1H, ddd, J=2.2 Hz, 8.0 Hz, 8.8 Hz), 7.27-7.36 (2H, m), 7.83 (1H, ddd, J=0.6 Hz, 1.2 Hz, 8.4 Hz), 7.95-8.06 (2H, m), 8.44 (1H, ddd, J=0.6 Hz, 1.8 Hz, 4.8 Hz), 12.37 (1H, br s), hidden (1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | R.2.45 4-Chloro-5-fluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid Reference Example 2-45 4-Chloro-5-fluoro-2-[[3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-yl]amino]benzoic acid Following the procedure described in Reference Example 2-5, the title compound was prepared from 2,4-dichloro-5-fluorobenzoic acid and 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (24% yield). mp: 245-246° C. (recrystallized from ethyl acetate). NMR (DMSO-d6) δ: 2.25 (3H, s), 6.28 (1H, s), 7.28-7.35 (1H, m), 7.64 (1H, d, J=6.6 Hz), 7.80-7.85 (2H, m), 7.95-8.03 (1H, m), 8.42 (1H, dd, J=1.2 Hz, 4.8 Hz), 12.21 (1H, br s), hidden (1H). |