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[ CAS No. 53929-59-2 ]

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Chemical Structure| 53929-59-2
Chemical Structure| 53929-59-2
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Product Details of [ 53929-59-2 ]

CAS No. :53929-59-2 MDL No. :MFCD00209967
Formula : C6H9N3 Boiling Point : 317.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :123.16 g/mol Pubchem ID :-
Synonyms :

Safety of [ 53929-59-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53929-59-2 ]

  • Downstream synthetic route of [ 53929-59-2 ]

[ 53929-59-2 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 6635-86-5 ]
  • [ 53929-59-2 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen;5% Pd(II)/C(eggshell); In methanol; at 20℃; under 760.051 Torr; for 2h; Example 1. Preparation of N-Cthiazol^-yl^-CS-CtrifluoromethyOphenyO-SH- imidazo[4,5-b]pyridine-7-carboxamide (Compound 100): Step 1) Synthesis of 4-methylpyridine-2,3-diamine (2):;1 24-Methyl-3-nitropyridin-2-amine (1; 2.0 g, 13 mmol) was dissolved in methanol (30 mL). After a catalytic amount of 5% Pd/C (100 mg) was added, and the mixture was stirred under 1 atm of hydrogen at room temperature for 2 h. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated under a reduced pressure to afford 4-methylpyridine-2, 3-diamine 2 as a brown solid (1.84 g, yield: 100%). This material was used in the next step without additional purification. MS (ESI) calcd for C6H9N3: 123.2; found: 124 [M+H].
97% With hydrogen;5%-palladium/activated carbon; In methanol; at 20℃; under 1034.32 Torr; for 3.5h; Shake a mixture of commercially available 4-methyl-3-nitro- pyridin-2-ylamine (5. 00 g, 32.65 mmol) and 5% palladium on carbon (750 mg) in methanol (200 mL) at room temperature under hydrogen (20 psi) in a Parr bottle for 3.5 h. Filter the mixture through a plug of Celite, eluting with methanol (2 x 50 mL) and remove the filtrate solvent under reduced pressure to afford 4-methylpyridine-2,3-diamine (Step 1) as yellow solid, which is used in the next step without further purification (3.92 g, 97%): APCI MS M/Z 124 [C6HGN3 + H] +.
97% With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; Commercially available 2-amino-4-methyl-3nitropyridine (10.0 g, 65.3 mmol) was suspended in ethanol (450 mL) and the flask was filled with argon. 10% palladium carbon (13.9 g, 50% water-containing) was added to the mixture and stirred at room temperature overnight under the flow of hydrogen. Solids were filtered through Celite and this was washed with ethanol. The filtrate was concentrated under reduced pressure to obtain Compound P12 (7.81 g, 63.3 mmol, 97%). ESI-MS: m/z 124 [M + H]+ 1H NMR (CDCl3)delta(ppm): 2.17 (s, 3H), 3.27 (brs, 2H), 4.16 (brs, 2H), 6.53 (d, J = 5.3 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H).
92% With methanol;5%-palladium/activated carbon; for 2h; 4-Methyl-3-nitropyridine-2-amine (25 g, 163.4 mmol) was dissolved in 100 ml of MeOH, and a catalytic amount of 5% Pd/C was added thereto, and the mixture was stirred for 2 hrs. The reaction solution was filtered through a celite pad, the pad was thoroughly washed with MeOH, and the combined mixture was concentrated under a reduced pressure to remove the solvent. The resulting residue was vacuum dried to obtain the title compound (18.49 g, 150.33 mmol; yield: 92 %). 1H-NMR (CDCl3): 2.17 (s, 3H), 3.27 (br, 2H), 4.14 (br, 2H), 6.54 (d,2H), 7.55 (d, 2H) M. W.: 124
67% With hydrogen;5%-palladium/activated carbon; In acetic acid; at 20℃; under 760.051 Torr; for 3h; 7.5 g of 5 % palladium-carbon catalyst (water content 50 %) was added to acetic acid (300 ml) solution of 15.0 g (97.9 mmol) of <strong>[6635-86-5]2-amino-4-methyl-3-nitropyridine</strong>, and the resulting mixture was stirred under atmospheric pressure of hydrogen at room temperature for 3 hours. After filtrating and concentrating under reduced pressure, the residue was dissolved in aqueous 10 % sodium carbonate solution and concentrated under reduced pressure. The residue was dissolved in mixed solution of chloroform/methanol (3/1, v/v) , and the insoluble material was removed through filtration. This was applied to a silica gel column chromatography. From the eluate with chloroform/methanol (20/1, v/v) , a pink-brown solidwas obtained. From the 1H-NMR, since the presence of acetic acid therein was confirmed, this solid was again dissolved in aqueous 10 % sodium carbonate solution and concentrated under reduced pressure. The residue was dissolved in chloroform, dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure and the resulting residue was dried to obtain 8.13 g (67 %) of the entitled compound as a yellow-brown solid. MS(FAB)m/z:124(M+1)+.1H-NMR(CD3OD)delta: 2.14(3H, s) , 6.46(2H, t, J=5.4Hz) , 7.27(2H, t, J=5.4Hz).
37% With iron; ammonium chloride; In water; isopropyl alcohol; at 70℃; for 2h; c) 4-Methylpyridine-2,3-diamine (A21) Iron powder (0.365 g, 6.53 mmol) and NH4CI (0.349 g, 6.53 mmol) were added to a stirred suspension of 4-methyl-3-nitropyridin-2-amine A17 (0.200 g, 1.31 mmol) in /-PrOH (10 mL) and water (5 mL). The reaction was heated to 70 C and stirred for 2 hours. The reaction was then cooled and filtered through a plug of celite, which was washed with EtOAc (75 mL). The filtrate was washed with saturated aqueous NaHC03 (75 mL), brine (75 mL), dried (Na2S04), filtered and concentrated in vacuo to give the title compound (0.060 g, 37%) as a dark purple solid. H NMR (400 MHz, CDCI3): delta 7.55 (d, J = 5.1 Hz, 1 H), 6.53 (d, J = 5.1 Hz, 1 H), 4.19 (br s, 2H), 3.26 (brs, 2H), 2.16 (s, 3H). LCMS-B: rt 0.74 min, m/z (positive ion) 124.1 [M+H]+.
palladium dihydroxide; In methanol; EXAMPLE 17 STR19 2,3-Diamino-4-methylpyridine A solution of <strong>[6635-86-5]2-amino-4-methyl-3-nitropyridine</strong> (Aldrich 10 Chemical Co., 500 mg) in methanol (3 mL) was treated with palladium hydroxide on carbon (50 mg) and stirred under a hydrogen atmosphere (1 atm) at room temperature for 6 h. The mixture was filtered through a pad of celite filter aid and the solvent removed by rotoevaporation to give the title compound (340 mg). Mass spectrum (FAB): m/e=124 (M+1).
palladium-carbon; In ethanol; Step A: Preparation of 2,3-diamino-4-picoline (cf. Lappin, G. R.; Slezak, F. B. J. Am. Chem. Soc., 1950, 72, 2806-7) To a slurry of <strong>[6635-86-5]2-amino-4-methyl-3-nitropyridine</strong> (10.0 g, 65.3 mmol) in 350 mL of 95% EtOH was added 500 mg of a 10% Pd/C catalyst. The mixture was stirred under a H2 atmosphere (1 atm) for 36 hours. Filtration and evaporation gave 8.05 g of a black solid which was used directly in the next step.
palladium-carbon; In ethanol; Step A: Preparation of 2,3-diamino-4-picoline (cf. Lappin, G. R.; Slezak, F. B. J. Am. Chem. Soc., 1950, 72,2806-7) To a slurry of <strong>[6635-86-5]2-amino-4-methyl-3-nitropyridine</strong> (10.0 g, 65.3 mmol) in 350 ml of 95% EtOH was added 500 mg of a 10% Pd/C catalyst. The mixture was stirred under a H2 atmosphere (1 atm) for 36 hours. Filtration and evaporation gave a black solid which was used directly in the next step.
With hydrogen;nickel; In methanol; under 2280.15 Torr; for 1.5 - 2h;Product distribution / selectivity; Raney Nickel (2.5 g) is added to a mixture of commercially available 4-methyl-3- nitro-pyridin-2-ylamine x175 (7.0 g, 45.7 mmol) in methanol (300 ml), and the obtained reaction mixture is hydrogenated in the Parr apparatus at the hydrogen pressure 3 atm EPO <DP n="134"/>until the total conversion of compound x175 is attained for approximately 1.5-2 h. The catalyst is separated by filtration, the filtrate is washed with methanol, and the alcohol solution is evaporated to dryness. CH(OMe)3 (100 ml) and PTSA (0.5 g) are added to the residue, and an air reflux condenser is mounted. The apparatus is argon-blown, and the obtained reaction mixture is heated to 125 0C under vigorous stirring for 1O h. The formed solution is evaporated, and the residue is dissolved in 5 % HCI (100 ml). The solution is refluxed for 1 h and evaporated to one-third volume. The solution is neutralized to pH 7 and extracted with 10 % tert-butanol in chloroform (4 x 100 ml). The organic layer is dried over anhydrous Na2SO4, and the solvent is evaporated. The residue is purified by chromatography on silicagel (chloroform/methanol) to afford 7-methyl-3H-imidazo[4,5- b]pyridine x176.Yield: 70 %.LC-IvIS (MH+): 134.; Raney Ni (1.5 g) is added to a mixture of commercially available nitrogen- containing 4-methyl-3-nitropyridin-2-amine x220 (4.0 g, 26.1 mmol) in methanol (150 ml), and the obtained reaction mixture is hydrogenated in the Parr apparatus at the hydrogen pressure 3 atm until the total conversion of compound x220 is attained for approximately 1.5-2 h. The catalyst is separated by filtration, the filtrate is washed with methanol, and the alcohol solution is evaporated to dryness. The residue is dissolved in sulfolane (10 ml), then PhC(OMe)3 (5.7 g, 1.2 eq, 31.3 mmol) and PTSA (0.3 g) are added, and an air reflux condenser is mounted. The apparatus is argon-blown, and the obtained reaction mixture is heated to 165 0C under vigorous stirring for 10 h. Water (100 ml), saturated aqueous NaHCC>3 (5 ml), and hexane (50 ml) are added to the reaction mixture. The obtained suspension is stirred for 5 min, and the residue is separated by filtration. The residue is washed with water (50 ml) and hexane (100 ml), and vacuum-dried over P2O5 to a constant weight at 45 0C to give 7-methyl-2-phenyl-3H-imidazo[4,5-b]pyridine x221 (2.2 g).Yield: 40 %. LC-MS (MH+): 210.
In ethanol; 2,3-Diamino-4-methylpyridine (56) A mixture of <strong>[6635-86-5]2-amino-4-methyl-3-nitropyridine</strong> (919 mg, 6.0 mmol), ethanol (20 mL) and Raney Ni (about 200 mg) was shaken under H2 (30-40 psi) for 1 h, then filtered. The filtrate was evaporated to dryness, giving 740 mg (100%) of the diamine 56, mp 114-5 C. 1 H NMR (DMSO-d6), 1.997 (s, 3H), 4.359 (s, 2H), 5.250 (s, 2H), 6.264 (d, 1H, J=3), 7.173 (d, 1H, J=3).
palladium-carbon; In ethanol; Step A: Preparation of 2,3-diamino-4-picoline (cf. Lappin, G. R.; Slezak, F. B. J. Am. Chem. Soc., 1950, 72, 2806-7) To a slurry of <strong>[6635-86-5]2-amino-4-methyl-3-nitropyridine</strong> (10.0 g, 65.3 mmol) in 350 mL of 95% EtOH was added 500 mg of a 10% Pd/C catalyst. The mixture was stirred under a H2 atmosphere (1 atm) for 36 hours. Filtration and evaporation gave 8.05 g of a black solid which was used directly in the next step.

  • 2
  • [ 53929-59-2 ]
  • [ 79-14-1 ]
  • [ 115951-72-9 ]
YieldReaction ConditionsOperation in experiment
52% at 140 - 150℃; for 3h;
  • 3
  • [ 53929-59-2 ]
  • [ 107-92-6 ]
  • [ 133239-98-2 ]
YieldReaction ConditionsOperation in experiment
With PPA at 80 - 90℃;
  • 4
  • [ 53929-59-2 ]
  • [ 802294-64-0 ]
  • [ 133240-12-7 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: 4-methyl-2,3-diaminopyridine; propionic acid at 100℃; for 3h; Stage #2: With ammonia; sodium carbonate In water for 1h; 13 Compound P12 (1.80 g, 14.6 mmol) was suspended in polyphosphoric acid (38 g), and propionic acid (3.27 mL, 43.8 mmol) was added to the solution, followed by stirring at 100°C for 3 hours. The reaction mixture was moved to ice water, and sodium carbonate was added in a little portion while stirring. Then, 28 % aqueous ammonia solution was added to the mixture to control the pH to 9 and the mixture was stirred for 1 hour. The reaction mixture was extracted with chloroform twice, and the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform: methanol=50:1) to obtain compound P13 (2.24 g, 14.0 mmol, 96%). ESI-MS: m/z 162 [M + H]+ 1H NMR (CDCl3)δ(ppm): 1.53 (t, J = 7.7 Hz, 3H), 2.68 (s, 3H), 3.08 (q, J = 7.7 Hz, 2H), 7.02 (d, J = 5.1 Hz, 1H), 8.17 (d, J = 4.9 Hz, 1H), 14.1 (brs, 1H).
79% With PPA at 100℃; for 5h;
24% Stage #1: 4-methyl-2,3-diaminopyridine; propionic acid at 130℃; for 36h; Stage #2: propionic acid With PPA at 80℃; for 24h; Stage #3: With sodium hydroxide 2 Step 2. Preparation of 2-ethyl-7-methylirnidazo-(4,5-b)pyridine; 4-Methyl-pyridine-2,3-diamine (24g, 195 mmol) was dissolved in propionic acid ( 25 mL, 270 mmol) and heated at 1300C for 12 hours. As starting material and product were observed, heating continued an additional 24 h. 50Og of polyphosphoric acid and 50 mL propionic acid were added and the reaction heated at 8O0C for 24 hours. Reaction progress was monitored by mass spectroscopy (M+1 =162.0). After starting material mass was consumed, the reaction mixture was poured over ice, and pH basified with solid NaOH. Aqueous solution extracted with EtOAc (5 x 75 mL). Solvent was removed in vacuo and the residue purified by silica gel chromatography to give 2-ethyl-7- methylimidazo-(4,5-b)pyridine (7.7 g, 24% yield). 1 H NMR (400 MHz, DMSO-D6) δ ppm 1.3 (q, J=7.7 Hz, 3 H) 2.5 (s, 3 H) 2.8 (m, 2 H) 6.9 (d, J=4.9 Hz, 1 H) 8.0 (m, 1 H) 12.5 (d, J=99.8 Hz, 1 H)
  • 7
  • [ 53929-59-2 ]
  • [ 148402-26-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 79 percent / polyphosphoric acid / 5 h / 100 °C 2: 76 percent / Cs2CO3 / dimethylformamide / 24 h / Ambient temperature 3: 90 percent / conc. aq. HCl / ethanol / 2 h / Heating
  • 8
  • [ 53929-59-2 ]
  • 4'-(2-Ethyl-7-methyl-imidazo[4,5-b]pyridin-3-ylmethyl)-biphenyl-2-sulfonic acid 1-dimethylamino-meth-(E)-ylideneamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 79 percent / polyphosphoric acid / 5 h / 100 °C 2: 76 percent / Cs2CO3 / dimethylformamide / 24 h / Ambient temperature
  • 9
  • [ 53929-59-2 ]
  • C25H26N4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 79 percent / polyphosphoric acid / 5 h / 100 °C 2: 76 percent / Cs2CO3 / dimethylformamide / 24 h / Ambient temperature 3: 90 percent / conc. aq. HCl / ethanol / 2 h / Heating 4: 74 percent / K2CO3 / 1,2-dimethoxy-ethane / 6 h / Heating
  • 10
  • [ 53929-59-2 ]
  • 3-[(2'-allylaminocarbonylaminosulfonylbiphenyl-4-yl)-methyl]-2-ethyl-7-methyl-imidazo[4,5-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 79 percent / polyphosphoric acid / 5 h / 100 °C 2: 76 percent / Cs2CO3 / dimethylformamide / 24 h / Ambient temperature 3: 90 percent / conc. aq. HCl / ethanol / 2 h / Heating 4: 94 percent / K2CO3 / acetone / 3 h / Heating
  • 11
  • [ 53929-59-2 ]
  • 2-Ethyl-7-methyl-3-[(2'-n-propylaminocarbonyl-aminosulfonylbiphenyl-4-yl) methyl]-imidazo[4,5-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 79 percent / polyphosphoric acid / 5 h / 100 °C 2: 76 percent / Cs2CO3 / dimethylformamide / 24 h / Ambient temperature 3: 90 percent / conc. aq. HCl / ethanol / 2 h / Heating 4: 71 percent / K2CO3 / acetone / 3 h / Heating
  • 12
  • [ 53929-59-2 ]
  • C26H28N4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 79 percent / polyphosphoric acid / 5 h / 100 °C 2: 76 percent / Cs2CO3 / dimethylformamide / 24 h / Ambient temperature 3: 90 percent / conc. aq. HCl / ethanol / 2 h / Heating 4: 40 percent / K2CO3 / 1,2-dimethoxy-ethane / 6 h / Heating
  • 13
  • [ 53929-59-2 ]
  • C27H29N5O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 79 percent / polyphosphoric acid / 5 h / 100 °C 2: 76 percent / Cs2CO3 / dimethylformamide / 24 h / Ambient temperature 3: 90 percent / conc. aq. HCl / ethanol / 2 h / Heating 4: Cs2CO3 / dimethylformamide / 1 h / 80 °C
  • 14
  • [ 53929-59-2 ]
  • C30H29N5O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 79 percent / polyphosphoric acid / 5 h / 100 °C 2: 76 percent / Cs2CO3 / dimethylformamide / 24 h / Ambient temperature 3: 90 percent / conc. aq. HCl / ethanol / 2 h / Heating 4: 65 percent / K2CO3 / acetone / 3 h / Heating
  • 15
  • [ 53929-59-2 ]
  • C30H28N4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 79 percent / polyphosphoric acid / 5 h / 100 °C 2: 76 percent / Cs2CO3 / dimethylformamide / 24 h / Ambient temperature 3: 90 percent / conc. aq. HCl / ethanol / 2 h / Heating 4: 83 percent / K2CO3 / 1,2-dimethoxy-ethane / 6 h / Heating
  • 16
  • [ 53929-59-2 ]
  • [ 115951-65-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 80 percent / 5 h / Heating 2: 85 percent / H2O / 0.25 h / Heating 3: 50 percent / KMnO4, Na2CO3 / H2O / 2 h / Heating 4: 70 percent / conc. H2SO4 / 8 h / Heating 5: 52 percent / conc. NH3 / 0.17 h / Heating 6: 56 percent / POCl3 / 5 h / Heating
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