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[ CAS No. 478169-74-3 ] {[proInfo.proName]}

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Chemical Structure| 478169-74-3
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Product Details of [ 478169-74-3 ]

CAS No. :478169-74-3 MDL No. :MFCD03086078
Formula : C9H7NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :QFCJSANSFSOSQM-UHFFFAOYSA-N
M.W : 177.16 Pubchem ID :22610021
Synonyms :

Calculated chemistry of [ 478169-74-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.93
TPSA : 63.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 1.63
Log Po/w (WLOGP) : 1.83
Log Po/w (MLOGP) : 1.04
Log Po/w (SILICOS-IT) : 1.69
Consensus Log Po/w : 1.55

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -2.41
Solubility : 0.687 mg/ml ; 0.00388 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.474 mg/ml ; 0.00268 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.67
Solubility : 0.376 mg/ml ; 0.00212 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.23

Safety of [ 478169-74-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 478169-74-3 ]

* 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.

  • Downstream synthetic route of [ 478169-74-3 ]

[ 478169-74-3 ] Synthesis Path-Downstream   1~37

  • 1
  • [ 478169-74-3 ]
  • [ 6148-64-7 ]
  • [ 1607024-89-4 ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: 3-methylbenzo[d]isoxazole-5-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 40℃; for 2h; Stage #2: ethyl potassium malonate With triethylamine; magnesium chloride In tetrahydrofuran; acetonitrile at 20℃; for 1h; 90.5 Step 5: ethyl 3-(3-methylbenzo[d]isoxazol-5-yl)-3-oxopropanoate To a solution of 3-methylbenzo[d]isoxazole-5-carboxylic acid (4.0 g, 22.58 mmol, 1.00 equiv) in tetrahydrofuran (50 mL) was added CDI (11 g, 67.90 mmol, 3.00 equiv). The reaction was stirred for 2 h at 40°C. Separately, to a solution of potassium 3-ethoxy-3-oxopropanoate (10.2 g, 59.93 mmol, 3.00 equiv) in CH3CN (150 mL) was added triethylamine (6.06 g, 59.89 mmol, 3.00 equiv) and MgCl2 (8.55 g, 90.00 mmol, 4.50 equiv). The two solutions were combined and stirred for 1 h at room temperature. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether = 1 :5). The resulting mixture was concentrated under vacuum. The residue was diluted with 200 mL of H20. The pH of the solution was adjusted to pH 4 with aq. HCl (4M). The resulting solution was extracted with 4x50 mL of ethyl acetate and the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1 :50) to provide 4.5 g (81 ) of ethyl 3-(3-methylbenzo[d]isoxazol-5-yl)-3-oxopropanoate as an off-white solid. LC-MS (ES, m/z) [M+H] + 248.0 'H NMR (300 MHz, CDC13): δ 8.33 (s, 1H), 8.21-8.19 (m, 1H), 7.64 (d, / = 6. 1H), 4.34-4.23 (m, 2H), 4.10 (s, 2H), 2.69 (s, 3H), 1.40-1.27 (m, 3H)
  • 2
  • [ 1607024-88-3 ]
  • [ 478169-74-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; N-chloro-succinimide / tetrahydrofuran / 10 h / 20 °C 2: sodium hydroxide; water / methanol / 20 °C
  • 3
  • [ 57009-12-8 ]
  • [ 478169-74-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ammonia / methanol / 20 °C 2: potassium carbonate; N-chloro-succinimide / tetrahydrofuran / 10 h / 20 °C 3: sodium hydroxide; water / methanol / 20 °C
Multi-step reaction with 3 steps 1: sodium acetate; hydroxylamine hydrochloride / water; ethanol / 1.17 h / Reflux 2: <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal / 1,4-dioxane / 0.12 h / 100 °C 3: sodium hydroxide / water; methanol / 5 h / 20 °C
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol; water / 1.17 h / Reflux 2: <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal / 1,4-dioxane / 0.12 h / 100 °C 3: methanol; sodium hydroxide / water / 20 °C
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; sodium acetate / ethanol; water / 2 h / 80 °C / Inert atmosphere 2: <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal / 1,4-dioxane / 2 h / 85 °C / Inert atmosphere 3: sodium hydroxide; methanol; water / 10 h / 20 °C

  • 4
  • [ 1450-75-5 ]
  • [ 478169-74-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine / 100 °C 2: ammonia / methanol / 20 °C 3: potassium carbonate; N-chloro-succinimide / tetrahydrofuran / 10 h / 20 °C 4: sodium hydroxide; water / methanol / 20 °C
  • 5
  • [ 1374962-06-7 ]
  • [ 478169-74-3 ]
YieldReaction ConditionsOperation in experiment
97% With sodium hydroxide In methanol; water at 20℃; for 5h;
97.1% With methanol; sodium hydroxide In water at 20℃; 5 Step 5. Preparation of 3-methylbenzo[d]isoxazole-5-carboxylic acid G-1: Compound F-1 (3.0 g, 15.7 mmol) was dissolved in MeOH (30 mL).After completion, the methanol was depressurized under reduced pressure, cooled to 0 ° C, and the mixture was acidified to pH 5-6.The precipitated solid was collected by filtration, washed with water and dried under reduced pressure.The title compound was obtained as a white solid (2.7 g, 97.1% yield).
90% With water; sodium hydroxide In methanol at 20℃; 110.4 Step 4: 3-methylbenzo[d]isoxazole-5-carboxylic acid Into a 500-mL round-bottom flask, was placed a solution of methyl 3- methylbenzo[d]isoxazole-5-carboxylate (10 g, 52.3 mmol, 1.00 equiv) in methanol (100 mL), and a solution of sodium hydroxide (8.4 g, 210 mmol, 4.00 equiv) in water (10 mL) was added. The reaction was stirred overnight at room temperature and progress was monitored by TLC (ethyl acetate/petroleum ether = 1 : 1). The resulting mixture was concentrated in vacuo. The residue was dissolved in 100 mL of water. The pH of the solution was adjusted to pH 4 with HC1 (4M). The solids were collected by filtration. The solid was dried in an oven in vacuo. This resulted in 8.0 g (90%) of 3-methylbenzo[d]isoxazole-5-carboxylic acid as a light yellow solid. LC-MS (ES, m/z): 178 [M+H]+
With sodium hydroxide In methanol; water
With methanol; water; sodium hydroxide at 20℃; for 10h; 3-methyl-1,2-benzoxazole-5-carboxylic acid as a white solid (Acid B) Into a 50-mL round-bottom flask, was placed methyl 3-methyl-1,2-benzoxazole-5- carboxylate (1-3, 1.0 g, 5.23 mmol, 1.0 equiv), MeOH (10.0 mL), H2O (3.0mL), sodium hydroxide (1.05 g, 26.3 mmol, 5.02 equiv). The resulting solution was stirred for 10 hr at room temperature. The resulting mixture was concentrated. The resulting solution was diluted with 20 mL of H2O and extracted with 2x20 mL of ethyl acetate and the aqueous layers combined. The pH value of the solution was adjusted to pH 3 and the resulting solids were collected by filtration.1H -NMR: (300 MHz, DMSO-d6,ppm) δ 13.17 (s, 1H), 8.47 (dd, J = 1.8, 0.7 Hz, 1H), 8.21 (dd, J = 8.8, 1.7 Hz, 1H), 7.79 (dd, J = 8.7, 0.7 Hz, 1H), 2.61 (s, 3H).

  • 6
  • [ 478169-74-3 ]
  • [ 1607023-43-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 40 °C 1.2: 1 h / 20 °C 2.1: toluene-4-sulfonic acid / butan-1-ol / 1 h / 120 °C
  • 7
  • [ 478169-74-3 ]
  • [ 1607023-44-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 40 °C 1.2: 1 h / 20 °C 2.1: toluene-4-sulfonic acid / butan-1-ol / 2 h / Reflux
  • 8
  • [ 478169-74-3 ]
  • [ 1607025-07-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 40 °C 1.2: 1 h / 20 °C 2.1: toluene-4-sulfonic acid / butan-1-ol / 2 h / 130 °C
  • 9
  • [ 478169-74-3 ]
  • [ 1607025-08-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 40 °C 1.2: 1 h / 20 °C 2.1: toluene-4-sulfonic acid / butan-1-ol / 2 h / 130 °C 3.1: water; sulfuric acid / 6 h / 25 °C
  • 10
  • [ 478169-74-3 ]
  • [ 1607023-63-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 2 h / 40 °C 1.2: 1 h / 20 °C 2.1: toluene-4-sulfonic acid / butan-1-ol / 2 h / 130 °C 3.1: water; sulfuric acid / 6 h / 25 °C 4.1: toluene-4-sulfonic acid / 1-methyl-pyrrolidin-2-one / 1 h / 110 °C
  • 12
  • methyl 4-hydroxy-3-(1-(hydroxyimino)ethyl)benzoate [ No CAS ]
  • [ 478169-74-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal / 1,4-dioxane / 0.12 h / 100 °C 2: sodium hydroxide / water; methanol / 5 h / 20 °C
  • 13
  • [ 478169-74-3 ]
  • 5-morpholino-N<SUP>1</SUP>-propylbenzene-1,2-diamine [ No CAS ]
  • 3-methyl-N-(4-morpholino-2-(propylamino)phenyl)benzo[d]isoxazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
230 mg Stage #1: 3-methylbenzo[d]isoxazole-5-carboxylic acid 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℃; for 0.25h; Stage #2: 5-morpholino-N<SUP>1</SUP>-propylbenzene-1,2-diamine In N,N-dimethyl-formamide at 20℃; for 12h;
230 mg 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 at 20℃; 1.1 Step 1. Preparation of 3-methyl-N-(4-morpholino-2-(propylamino)phenyl)benzo[d]isoxazole-5-carboxamide L-1: Compound G-1 (200.7 mg, 1.13 mmol), diisopropylethylamine (438.15 mg, 3.39 mmol)And HATU (644.5 mg, 1.70 mmol) was dissolved in 10 mL DMF.The reaction mixture was stirred for 15 min then compound K-1-1 (320.0 mg, 1.After completion of reaction, diluted with water and extracted with EtOAc (3 × 20mL).The combined organic layers were dried with anhydrous Na2SO~The crude product is purified by flash chromatography on silica gel to give the title compound.It was a white solid (230 mg, yield 51.6%).
  • 14
  • [ 478169-74-3 ]
  • 5-morpholino-N<SUP>1</SUP>-propylbenzene-1,2-diamine [ No CAS ]
  • 3-methyl-5-(6-morpholino-1-propyl-1H-benzo[d]imidazol-2-yl)benzo[d]isoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 12 h / 20 °C 2.1: acetic acid / 4 h / 120 °C
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / 20 °C 2: acetic acid / 3 h / 120 °C
  • 15
  • [ 478169-74-3 ]
  • C14H23N3O [ No CAS ]
  • 5-(1-butyl-6-morpholino-1H-benzo[d]imidazol-2-yl)-3-methylbenzo[d]isoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 12 h / 20 °C 2.1: acetic acid / 4 h / 120 °C
  • 16
  • [ 478169-74-3 ]
  • C14H23N3O [ No CAS ]
  • C23H28N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-methylbenzo[d]isoxazole-5-carboxylic acid 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℃; for 0.25h; Stage #2: C14H23N3O In N,N-dimethyl-formamide at 20℃; for 12h;
  • 17
  • [ 478169-74-3 ]
  • C13H21N3O2 [ No CAS ]
  • 5-(1-(2-methoxyethyl)-6-morpholino-1H-benzo[d]imidazol-2-yl)-3-methylbenzo[d]isoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 12 h / 20 °C 2.1: acetic acid / 4 h / 120 °C
  • 18
  • [ 478169-74-3 ]
  • C13H21N3O2 [ No CAS ]
  • C22H26N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-methylbenzo[d]isoxazole-5-carboxylic acid 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℃; for 0.25h; Stage #2: C13H21N3O2 In N,N-dimethyl-formamide at 20℃; for 12h;
  • 19
  • [ 478169-74-3 ]
  • C14H21N3O [ No CAS ]
  • 5-(1-(cyclopropylmethyl)-6-morpholino-1H-benzo[d]imidazol-2-yl)-3-methylbenzo[d]isoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 12 h / 20 °C 2.1: acetic acid / 4 h / 120 °C
  • 20
  • [ 478169-74-3 ]
  • C14H21N3O [ No CAS ]
  • C23H26N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-methylbenzo[d]isoxazole-5-carboxylic acid 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℃; for 0.25h; Stage #2: C14H21N3O In N,N-dimethyl-formamide at 20℃; for 12h;
  • 21
  • [ 478169-74-3 ]
  • N<SUP>1</SUP>-(sec-butyl)-5-morpholinobenzene-1,2-diamine [ No CAS ]
  • 5-(1-(sec-butyl)-6-morpholino-1H-benzo[d]imidazol-2-yl)-3-methylbenzo[d]isoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2-chloro-1-methyl-pyridinium iodide; tributyl-amine / toluene / 16 h / 90 °C / Inert atmosphere 2: acetic acid / 4 h / 120 °C
  • 22
  • [ 478169-74-3 ]
  • N<SUP>1</SUP>-(sec-butyl)-5-morpholinobenzene-1,2-diamine [ No CAS ]
  • N-(2-(sec-butylamino)-4-morpholinophenyl)-3-methylbenzo[d]isoxazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In toluene at 90℃; for 16h; Inert atmosphere;
  • 23
  • [ 478169-74-3 ]
  • [ 1610045-58-3 ]
  • 5-(1-benzyl-6-morpholino-1H-benzo[d]imidazol-2-yl)-3-methylbenzo[d]isoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2-chloro-1-methyl-pyridinium iodide; tributyl-amine / toluene / 16 h / 90 °C / Inert atmosphere 2: acetic acid / 4 h / 120 °C
  • 24
  • [ 478169-74-3 ]
  • [ 1610045-58-3 ]
  • C26H26N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In toluene at 90℃; for 16h; Inert atmosphere;
  • 25
  • [ 478169-74-3 ]
  • C17H27N3O [ No CAS ]
  • 5-(1-(cyclohexylmethyl)-6-morpholino-1H-benzo[d]imidazol-2-yl)-3-methylbenzo[d]isoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 12 h / 20 °C 2.1: acetic acid / 4 h / 120 °C
  • 26
  • [ 478169-74-3 ]
  • C17H27N3O [ No CAS ]
  • C26H32N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-methylbenzo[d]isoxazole-5-carboxylic acid 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℃; for 0.25h; Stage #2: C17H27N3O In N,N-dimethyl-formamide at 20℃; for 12h;
  • 27
  • [ 478169-74-3 ]
  • C18H29N3O [ No CAS ]
  • (S)-5-(1-(cyclohexylmethyl)-6-(3-methylmorpholino)-1H-benzo[d]imidazol-2-yl)-3-methylbenzo[d]isoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 12 h / 20 °C 2.1: acetic acid / 4 h / 120 °C
  • 28
  • [ 478169-74-3 ]
  • C18H29N3O [ No CAS ]
  • C27H34N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-methylbenzo[d]isoxazole-5-carboxylic acid 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℃; for 0.25h; Stage #2: C18H29N3O In N,N-dimethyl-formamide at 20℃; for 12h;
  • 29
  • methyl (Z)-4-hydroxy-3-(1-(hydroxyimino)ethyl)benzoate [ No CAS ]
  • [ 478169-74-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal / 1,4-dioxane / 0.12 h / 100 °C 2: methanol; sodium hydroxide / water / 20 °C
  • 30
  • [ 478169-74-3 ]
  • 2-(3-methylbenzo[d]isoxazol-5-yl)-1-propyl-1H-benzo[d]imidazole-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2-chloro-1-methyl-pyridinium iodide; tributyl-amine / toluene / 16 h / 90 °C / Inert atmosphere 2: acetic acid / 3 h / 120 °C
  • 31
  • [ 478169-74-3 ]
  • [ 475489-80-6 ]
  • N-(4-cyano-2-(propylamino)phenyl)-3-methylbenzo[d]isoxazol-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In toluene at 90℃; for 16h; Inert atmosphere; 16.1 Step 1. N-(4-Cyano-2-(propylamino)phenyl)-3-methylbenzo[d]isoxazol-5-carboxamide 3-methylbenzo[d]isoxazole-5-carboxylic acid (150 mg, 0.85 mmol), 4-amino-3-(propylamino)benzonitrile (148.4 mg, 0.85 mmol),2-Chloro-1-methylpyridinium iodide (CMPI) (521.2 mg, 2.04 mmol) and tri-n-butylamine were dissolved in 15 mL of toluene.The reaction mixture was heated to 90 ° C and stirred under N2 for 16 h.After completion, the solvent was removed by evaporation, water was added and extracted with EtOAc (3 × 20mL).The combined organic layers were dried with anhydrous Na2SO~The crude product is purified by flash column chromatography on silica gel to give the title compound.It was a white solid (85 mg, yield 30.0%).
  • 32
  • [ 478169-74-3 ]
  • 1-(2,5-dichloropyridin-4-yl)azetidin-3-amine [ No CAS ]
  • C17H14Cl2N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide
  • 34
  • [ 66033-76-9 ]
  • [ 478169-74-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine / methanol / 18 h / 80 °C 2: sodium hydroxide / methanol; water
  • 35
  • [ 478169-74-3 ]
  • 2-[[(2S)-2-methylpyrrolidin-1-yl]methyl]-1-(2-trimethylsilylethoxymethyl)pyrrolo[3,2-c]pyridine-6-amine [ No CAS ]
  • 3-methyl-N-(2-[[(2S)-2-methylpyrrolidin-1-yl]methyl]-1-[[2-(trimethylsilyl)ethoxy]methyl]pyrrolo[3,2-c]pyridin-6-yl)-1,2-benzoxazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 24h; Inert atmosphere; Preparation of Example 2 Into a 8-mL vial purged and maintained under an inert atmosphere of nitrogen, was placed 2-[[(2S)-2-methylpyrrolidin -1-yl]methyl]-1-[[2- (trimethylsilyl)ethoxy]methyl]pyrrolo[3,2-c]pyridin-6-amine (Amine D, 150.0 mg, 0.42 mmol, 1.0 equiv), pyridine (3.00 mL), 3-methyl-1,2-benzoxazole-5-carboxylic acid (81.1 mg, 0.46 mmol, 1.10 equiv), EDCI (119.6 mg, 0.62 mmol, 1.5 equiv). The resulting solution was stirred at room temperature for 24hr. The resulting mixture was concentrated and diluted with of H2O. The resulting solution was extracted with 3x20 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2 x20 mL of brine. The resulting mixture was concentrated. This resulted in 300 mg (crude) of 3-methyl-N-(2-[[(2S)-2-methylpyrrolidin-1- yl]methyl] -1-[[2-(trimethylsilyl)ethoxy]methyl]pyrrolo[3,2-c]pyridin-6-yl)-1,2-benzoxazole-5- carboxamide as a brown solid. LCMS: [M+H]+=520.
  • 36
  • [ 478169-74-3 ]
  • 2-[[(2S)-2-methylpyrrolidin-1-yl]methyl]-1-(2-trimethylsilylethoxymethyl)pyrrolo[3,2-c]pyridine-6-amine [ No CAS ]
  • 3-methyl-N-(2-[[(2S)-2-methylpyrrolidin-1-yl]methyl]-1H-pyrrolo[3,2-c]pyridin-6-yl)-1,2-benzoxazole-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 24 h / 20 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 16 h / 20 °C / Inert atmosphere
  • 37
  • methyl 4-hydroxy-3-[(1E)-1-(hydroxyimino)ethyl]benzoate [ No CAS ]
  • [ 478169-74-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal / 1,4-dioxane / 2 h / 85 °C / Inert atmosphere 2: sodium hydroxide; methanol; water / 10 h / 20 °C
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