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[ CAS No. 1005785-85-2 ]

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Chemical Structure| 1005785-85-2
Chemical Structure| 1005785-85-2
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Product Details of [ 1005785-85-2 ]

CAS No. :1005785-85-2 MDL No. :MFCD15526816
Formula : C10H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :179.22 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1005785-85-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1005785-85-2 ]

  • Downstream synthetic route of [ 1005785-85-2 ]

[ 1005785-85-2 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 186581-53-3 ]
  • [ 1005785-85-2 ]
  • [ 215436-29-6 ]
  • 3
  • [ 1005785-85-2 ]
  • (2-methyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methanamine [ No CAS ]
  • 5-(tert-butyl)-N-(2-methyl-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzyl)picolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% A solution of carboxylic acid (80 mg, 0.45 mmol) and CDI (145 mg, 0.90 mmol) in DMF (4 mL) was stirred at rt for 0.5 h, followed by the addition of the amine (110 mg, 0.45 mmol) and Et3N (137 mg, 1.35 mmol) and the mixture was stirred at rt for 16 h. After diluted with water (5 mL), the mixture was extracted with EtOAc (5 mL x 2). The combined organics were concentrated in vacuo and the residue was purified by reverse phase chromatography (MeOH/H2O with 0.05% NH3.H2O as mobile phase) to afford the title compound (26 mg, yield 15%) as a yellow solid. ESI-MS (M+H)+: 400.2.1H NMR (400 MHz, CD3OD) : 8.77-8.74 (m, 2H), 8.06-8.03 (m, 2H), 7.92-7.95 (m, 2H), 7.54-7.51 (m, 2H), 6.86 (d, J = 4.0 Hz, 1H), 4.74 (s, 2H), 2.53 (s, 3H), 1.42 (s, 9H).
  • 4
  • [ 1005785-85-2 ]
  • C14H11F3N4 [ No CAS ]
  • N-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-(trifluoromethyl)benzyl)-5-(tert-butyl)picolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20℃; for 2h; A solution of carboxylic acid (80 mg, 0.45 mmol) and CDI (145 mg, 0.90 mmol) in DMF (4 mL) was stirred at rt for 0.5 h, followed by the addition of the amine (110 mg, 0.45 mmol) and Et3N (137 mg, 1.35 mmol) and the mixture was stirred at rt for 16 h. After diluted with water (5 mL), the mixture was extracted with EtOAc (5 mL x 2). The combined organics were concentrated in vacuo and the residue was purified by reverse phase chromatography (MeOH/H2O with 0.05% NH3.H2O as mobile phase) to afford the title compound (26 mg, yield 15%) as a yellow solid. ESI-MS (M+H)+: 400.2.1H NMR (400 MHz, CD3OD) : 8.77-8.74 (m, 2H), 8.06-8.03 (m, 2H), 7.92-7.95 (m, 2H), 7.54-7.51 (m, 2H), 6.86 (d, J = 4.0 Hz, 1H), 4.74 (s, 2H), 2.53 (s, 3H), 1.42 (s, 9H).
  • 5
  • [ 102236-19-1 ]
  • [ 1005785-85-2 ]
  • 6
  • [ 215436-29-6 ]
  • [ 1005785-85-2 ]
YieldReaction ConditionsOperation in experiment
60 mg With lithium hydroxide; In tetrahydrofuran; water; at 50℃; for 1h; 5-tert-butylpyridine-2-carboxylic acid In a 50-mL round bottom flask, methyl 5-tert-butylpyridine-2-carboxylate (90 mg, 0.47 mmol, 1.00 equiv) was dissolved in a mixture of tetrahydrofuran and water (2:1, 3 mL), to which was added LiOH (40 mg, 1.67 mmol, 3.59 equiv) at room temperature. The resulting solution was then stirred for 1 h at 50 C. After the reaction was done, the reaction mixture was concentrated under reduced pressure. The pH value of the remaining solution was adjusted to 6 using HCl solution (1 M) and the resulting solution was extracted with ethyl acetate (3*30 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure to afford 5-tert-butylpyridine-2-carboxylic acid (60 mg, 68% for 2 steps) as yellow oil. MS: m/z=180.0[M+H]+
  • 7
  • [ 1005785-85-2 ]
  • 2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]benzylamine [ No CAS ]
  • 5-tert-butyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% 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℃; 5-tert-butyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-2-carboxamide In a 50-mL round bottom flask, [2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methanamine (90 mg, 0.28 mmol, 1.00 equiv) was dissolvent in N,N-dimethylformamide (15 mL), to which were added <strong>[1005785-85-2]5-tert-butylpyridine-2-carboxylic acid</strong> (60.3 mg, 0.34 mmol, 1.21 equiv), HATU (176 mg, 0.46 mmol, 1.66 equiv) and DIEA (120 mg, 0.93 mmol, 3.33 equiv) in sequence at room temperature. The resulting solution was then stirred overnight at room temperature. After the reaction was done, it was quenched by the addition of water (5 mL) and the resulting mixture was extracted with dichloromethane (3*20 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by prep-HPLC with the following conditions: column, XBridge Shield RP18 OBD Column, 5 um, 19*150 mm; mobile phase, MeCN in water (with 10 mM NH4HCO3), 40% to 57% gradient in 6 min; detector, UV 254 nm 5-tert-butyl-N-([2-fluoro-4-[2-(1-methyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]phenyl]methyl)pyridine-2-carboxamide (20 mg, 15%) was obtained as white solid. HPLC: 95.5% purity. MS: m/z=484.3 [M+H]+. 1H-NMR (400 MHz, DMSO-d6): delta 13.42 (br s, 1H), 9.35 (m, 1H), 8.73-8.72 (m, 1H), 8.44 (s, 1H), 8.27 (m, 2H), 8.13 (s, 2H), 8.02-8.00 (m, 2H), 7.48 (m, 2H), 4.64-4.62 (m, 2H), 3.94 (s, 3H), 1.36 (s, 9H).
  • 8
  • [ 40472-90-0 ]
  • [ 75-24-1 ]
  • [ 1005785-85-2 ]
YieldReaction ConditionsOperation in experiment
11% To a solution of 2-(6-methylpyridin-3-yl)propan-2-ol (0146) (0.31 g, 2.05 mmol, 1 equiv.) in CH2CI2 (10 ml) was added SOCI2 (0.727g, 6.16 mmol, 3 equiv.) dropwise at 0C with ice-cooling. The reaction mixture was stirred at bath temperature for 2 h and then concentrated to remove volatiles. The residue was then diluted with DCE (20 mL) and cooled to 0C. MesAl (2 M solution in Hexane, 2.1 mL, 4.31 mmol, 2.1 equiv.) was added dropwise and kept stirring for 3 h at 0C. Then the reaction mixture was slowly warmed up to 85 C and stirred for 18 h. The reaction was cooled to room temperature and quenched with NaHC03 (sat. 5 ml), then brine (5 ml). The mixture was filtered though a pad of celite and the filter cake was washed with CH2CI2. The filtrate and washings were washed with brine, dried over sodium sulfate, and concentrated in vacuo to give crude product as an unseparable mixture of 5-(tert-butyl)-2-methylpyridine and (5-(prop-l-en-2-yl)pyridin-2- yl)methylium. The crude product was used for next step without further purification. To a sealed tube was charged a suspension of 5-(tert-butyl)-2-methylpyridine, (5-(prop-l-en-2-yl)pyridin-2- yl)methylium and Se02 (1.14 g, 10.25 mmol, 5 equiv.) in pyridine (lOmL), the mixture was stirred at H0C for 18 h. After cooled down to room temperature, the mixture was diluted with MeOH and filtered, the filtrate was concentrated and purified via silica FCC (gradient elution from 30% EtOAc in Hexanes to 70% EtOAc in Hexanes) to give the desired product 5-(tert-butyl)picolinic acid pale solid (40 mg, 11% over three steps). ^-NMR (600 MHz,
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