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Chemical Structure| 635678-09-0
Chemical Structure| 635678-09-0
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Product Details of [ 635678-09-0 ]

CAS No. :635678-09-0 MDL No. :MFCD18157679
Formula : C16H23NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 293.36 Pubchem ID :-
Synonyms :

Safety of [ 635678-09-0 ]

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Application In Synthesis of [ 635678-09-0 ]

* 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 [ 635678-09-0 ]

[ 635678-09-0 ] Synthesis Path-Downstream   1~34

  • 1
  • [ 50-00-0 ]
  • [ 906565-52-4 ]
  • [ 635678-09-0 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: methyl 3-methoxy-4-(1-tert-butyloxycarbonylpiperidin-4-ylmethoxy)benzoate With formic acid at 20℃; for 0.005h; Stage #2: formaldehyd at 95℃; for 0.6h; Inert atmosphere; 1 Synthesis of Methyl 4-(N-methyl-4-piperidinylmethoxy)-3-methoxybenzoate Methyl 4-(N-Boc-4-piperidinylmethoxy)-3-methoxybenzoate (1g, 2.64mmol) was weighted into a 100 mL eggplant-shaped flask, and about 12 mL of formic acid was added, and stirred for about 30 min at room temperature for dissolving it. Afterwards, formaldehyde solution (4 mL, 47.44 mmol, 37%) was slowly added dropwise, heated under reflux at 95°C in an atomsphere of argon for about 6 h. The reaction was confirmed as being completed by TLC. The solvent was removed by a diaphragm pump. The crude product was separated by silica gel column chromatography (dichloromethane / methanol = 30: 1) to obtain 730 mg of methyl 4-(N-methyl-4-piperidinylmethoxy)-3-methoxybenzoate as a white solid with a yield of 94%. 1H NMR(400MHz, DMSO): δ 7.57 (d, J= 8.4Hz, 1H), 7.42 (s, 1H), 7.10 (d, J= 8.4Hz, 1H), 3.94 (d, J = 6Hz, 2H), 3.82 (s, 3H), 3.81 (s, 3H), 3.25 (d, J = 12Hz, 2H), 2.70 (dd, J1 = 11.2Hz, J2 = 22.8Hz, 2H), 2.6 (s, 3H), 1.97-1.80 (m, 1H), 1.88 (d, J= 21.6Hz, 2H), 1.49-1.40 (m, 2H).
With formic acid
0.43 g Stage #1: methyl 3-methoxy-4-(1-tert-butyloxycarbonylpiperidin-4-ylmethoxy)benzoate With formic acid at 20℃; for 0.5h; Stage #2: formaldehyd at 120℃; for 8h; Inert atmosphere;
  • 2
  • [ 635678-09-0 ]
  • [ 906565-53-5 ]
YieldReaction ConditionsOperation in experiment
78% With nitric acid; trifluoroacetic acid In dichloromethane at 25℃;
78% With nitric acid; trifluoroacetic acid In dichloromethane at 20℃; for 0.00625h; Cooling with ice; 1 Synthesis of methyl 6-nitro-4-(N-methyl-4-piperidinylmethoxy)-3-methoxybenzoate Methyl 4-(N-methyl-4-piperidinylmethoxy)-3-methoxybenzoate (500 mg, 1.7 mmol) was weighted into a 100 mL eggplant-shaped flask, and about 20 mL of DCM was added to dissolve it. About 2 mL of trifluoroacetic acid was slowly added dropwise in an ice bath, and 24 M fuming nitric acid (400 uL, 8.52mmol) was added dropwise within 15 minutes. The reaction was conducted at room temperature for about 6 h. After the reaction was completed, the pH was adjusted to 7 with saturated sodium bicarbonate aqueous solution, and the resulting system was extracted with saturated sodium chloride / ethyl acetate, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the crude product was separated by silica gel column chromatography (dichloromethane / methanol = 30: 1) to obtain 450 mg of light yellow oily methyl 6-nitro-4-(N-methyl-4-piperidinylmethoxy)-3-methylbenzoate with a yield of 78%. 1H NMR(400MHz, DMSO): δ 7.62 (s, 1H), 7.31 (s, 1H), 3.97 (d, J = 6Hz), 3.92 (s, 3H), 3.83 (s, 3H), 2.77 (d, J= 11.2 Hz, 2H), 2.15 (s, 3H), 1.86 (t, J = 11.2Hz, 2H), 1.76-1.74 (m, 1H), 1.72 (d, J = 10.4Hz, 2H), 1.30-1.25 (m, 2H).
With nitric acid; trifluoroacetic acid In dichloromethane
With nitric acid; trifluoroacetic acid In dichloromethane at 20℃;

  • 3
  • 3-methoxy-4-(piperidin-4-ylmethoxy)-benzoic acid methyl ester [ No CAS ]
  • [ 50-00-0 ]
  • [ 635678-09-0 ]
YieldReaction ConditionsOperation in experiment
80% With formic acid In water at 95℃;
  • 4
  • [ 3943-74-6 ]
  • [ 635678-09-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / CH2Cl2; toluene / 1 h / 20 °C 2: HCl / dioxane / 1 h / 20 °C 3: 80 percent / formic acid / H2O / 95 °C
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide 2: aq. HCO2H
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 5 h / 120 °C 2.1: formic acid / 0.5 h / 20 °C 2.2: 8 h / 120 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0 h / 20 °C 1.2: 3 h / Reflux 2.1: formic acid / 0.01 h / 20 °C 2.2: 0.6 h / 95 °C / Inert atmosphere

  • 5
  • [ 123855-51-6 ]
  • [ 635678-09-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 92 percent / triphenylphosphine; diethyl azodicarboxylate / CH2Cl2; toluene / 1 h / 20 °C 2: HCl / dioxane / 1 h / 20 °C 3: 80 percent / formic acid / H2O / 95 °C
  • 6
  • [ 635678-09-0 ]
  • 4-(3'-chloro-4'-fluoro)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C 2: hydrogen / palladium on activated carbon / methanol 3: 2-methoxy-ethanol / 2 h / 115 °C 4: oxalyl chloride / CHCl3; dimethylformamide / Heating 5: 88 percent / HCl / propan-2-ol / 2 h / Heating
  • 7
  • [ 635678-09-0 ]
  • [ 264208-72-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C 2: hydrogen / palladium on activated carbon / methanol 3: 2-methoxy-ethanol / 2 h / 115 °C 4: oxalyl chloride / CHCl3; dimethylformamide / Heating
Multi-step reaction with 4 steps 1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3: 2-methoxy-ethanol / 8 h / 120 °C 4: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating
Multi-step reaction with 4 steps 1: trifluoroacetic acid; nitric acid / dichloromethane / 0.01 h / 20 °C / Cooling with ice 2: palladium on activated charcoal; hydrogen / methanol / 6 h 3: 2-methoxy-ethanol / 3.67 h / 120 °C 4: N,N-dimethyl-formamide; thionyl chloride / 0.12 h / 20 °C / Cooling with ice
  • 8
  • [ 635678-09-0 ]
  • [ 264208-69-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C 2: hydrogen / palladium on activated carbon / methanol 3: 2-methoxy-ethanol / 2 h / 115 °C
Multi-step reaction with 3 steps 1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3: 2-methoxy-ethanol / 8 h / 120 °C
Multi-step reaction with 3 steps 1: trifluoroacetic acid; nitric acid / dichloromethane / 0.01 h / 20 °C / Cooling with ice 2: palladium on activated charcoal; hydrogen / methanol / 6 h 3: 2-methoxy-ethanol / 3.67 h / 120 °C
  • 9
  • [ 635678-09-0 ]
  • [ 635678-10-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C 2: hydrogen / palladium on activated carbon / methanol
Multi-step reaction with 2 steps 1: HNO3; TFA / CH2Cl2 2: H2 / Pd/C / methanol
Multi-step reaction with 2 steps 1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C
Multi-step reaction with 2 steps 1: trifluoroacetic acid; nitric acid / dichloromethane / 0.01 h / 20 °C / Cooling with ice 2: palladium on activated charcoal; hydrogen / methanol / 6 h

  • 10
  • [ 906565-52-4 ]
  • [ 635678-09-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: HCl / dioxane / 1 h / 20 °C 2: 80 percent / formic acid / H2O / 95 °C
  • 11
  • [ 166815-96-9 ]
  • [ 635678-09-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide 2: aq. HCO2H
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 5 h / 120 °C 2.1: formic acid / 0.5 h / 20 °C 2.2: 8 h / 120 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0 h / 20 °C 1.2: 3 h / Reflux 2.1: formic acid / 0.01 h / 20 °C 2.2: 0.6 h / 95 °C / Inert atmosphere
  • 12
  • [ 635678-09-0 ]
  • 6-methoxy-7-(1-methyl-piperidin-4-ylmethoxy)-4-oxo-3,4-dihydro-quinoline-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: HNO3; TFA / CH2Cl2 2: H2 / Pd/C / methanol 3: n-BuLi / tetrahydrofuran
  • 13
  • [ 635678-09-0 ]
  • 2-(dimethylamino-methyleneamino)-5-methoxy-4-(1-methyl-piperidin-4-ylmethoxy)-benzoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: HNO3; TFA / CH2Cl2 2: H2 / Pd/C / methanol
  • 14
  • [ 635678-09-0 ]
  • [ 423180-28-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: HNO3; TFA / CH2Cl2 2: H2 / Pd/C / methanol 3: n-BuLi / tetrahydrofuran 4: POCl3
  • 15
  • [ 635678-09-0 ]
  • 4-[(2,4-dichlorophenyl)amino]-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy-]-3-quinolinecarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: HNO3; TFA / CH2Cl2 2: H2 / Pd/C / methanol 3: n-BuLi / tetrahydrofuran 4: POCl3 5: NaH / tetrahydrofuran
  • 16
  • [ 635678-09-0 ]
  • 6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]-4-[(3,4,5-trimethoxyphenyl)amino]quinoline-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: HNO3; TFA / CH2Cl2 2: H2 / Pd/C / methanol 3: n-BuLi / tetrahydrofuran 4: POCl3 5: pyridine hydrochloride / 2-ethoxy-ethanol
  • 17
  • [ 635678-09-0 ]
  • 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]-3-quinolinecarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: HNO3; TFA / CH2Cl2 2: H2 / Pd/C / methanol 3: n-BuLi / tetrahydrofuran 4: POCl3 5: NaH / tetrahydrofuran
  • 18
  • [ 635678-09-0 ]
  • N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3.1: 2-methoxy-ethanol / 8 h / 120 °C 4.1: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5.1: isopropyl alcohol / 1 h / 20 °C 5.2: 8 h / 80 °C
Multi-step reaction with 5 steps 1.1: trifluoroacetic acid; nitric acid / dichloromethane / 0.01 h / 20 °C / Cooling with ice 2.1: palladium on activated charcoal; hydrogen / methanol / 6 h 3.1: 2-methoxy-ethanol / 3.67 h / 120 °C 4.1: N,N-dimethyl-formamide; thionyl chloride / 0.12 h / 20 °C / Cooling with ice 5.1: isopropyl alcohol / 1 h / 20 °C 5.2: 0.6 h / 80 °C
  • 19
  • [ 635678-09-0 ]
  • N-(4-fluoro-3-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3.1: 2-methoxy-ethanol / 8 h / 120 °C 4.1: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5.1: isopropyl alcohol / 1 h / 20 °C 5.2: 8 h / 80 °C
  • 20
  • [ 635678-09-0 ]
  • N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)-2-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3.1: 2-methoxy-ethanol / 8 h / 120 °C 4.1: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5.1: isopropyl alcohol / 1 h / 20 °C 5.2: 8 h / 80 °C
  • 21
  • [ 635678-09-0 ]
  • N-(4-fluoro-3-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)-2-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3.1: 2-methoxy-ethanol / 8 h / 120 °C 4.1: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5.1: isopropyl alcohol / 1 h / 20 °C 5.2: 8 h / 80 °C
  • 22
  • [ 635678-09-0 ]
  • 2-(2,3-dihydro-1H-inden-2-yl)-N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3.1: 2-methoxy-ethanol / 8 h / 120 °C 4.1: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5.1: isopropyl alcohol / 1 h / 20 °C 5.2: 8 h / 80 °C
  • 23
  • [ 635678-09-0 ]
  • 2-(2,3-dihydro-1H-inden-2-yl)-N-(4-fluoro-3-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3.1: 2-methoxy-ethanol / 8 h / 120 °C 4.1: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5.1: isopropyl alcohol / 1 h / 20 °C 5.2: 8 h / 80 °C
  • 24
  • [ 635678-09-0 ]
  • N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)-2-phenylpropionamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3.1: 2-methoxy-ethanol / 8 h / 120 °C 4.1: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5.1: isopropyl alcohol / 1 h / 20 °C 5.2: 8 h / 80 °C
  • 25
  • [ 635678-09-0 ]
  • N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)-3-methyl-2-phenylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3.1: 2-methoxy-ethanol / 8 h / 120 °C 4.1: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5.1: isopropyl alcohol / 1 h / 20 °C 5.2: 8 h / 80 °C
  • 26
  • [ 635678-09-0 ]
  • N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)-2,2-diphenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2.1: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3.1: 2-methoxy-ethanol / 8 h / 120 °C 4.1: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5.1: isopropyl alcohol / 1 h / 20 °C 5.2: 8 h / 80 °C
  • 27
  • [ 635678-09-0 ]
  • N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)-2-(1-oxoisoindolin-2-yl)-2-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3: 2-methoxy-ethanol / 8 h / 120 °C 4: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5: hydrogenchloride / isopropyl alcohol; water / 8 h / 80 °C
Multi-step reaction with 5 steps 1: trifluoroacetic acid; nitric acid / dichloromethane / 0.01 h / 20 °C / Cooling with ice 2: palladium on activated charcoal; hydrogen / methanol / 6 h 3: 2-methoxy-ethanol / 3.67 h / 120 °C 4: N,N-dimethyl-formamide; thionyl chloride / 0.12 h / 20 °C / Cooling with ice 5: hydrogenchloride / isopropyl alcohol; water / 6 h / 80 °C
  • 28
  • [ 635678-09-0 ]
  • N-(4-fluoro-3-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)-2-(1-oxoisoindolin-2-yl)-2-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3: 2-methoxy-ethanol / 8 h / 120 °C 4: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5: hydrogenchloride / isopropyl alcohol; water / 8 h / 80 °C
  • 29
  • [ 635678-09-0 ]
  • (S)-N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl )-2-(1-oxoisoindolin-2-yl)-2-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3: 2-methoxy-ethanol / 8 h / 120 °C 4: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5: hydrogenchloride / isopropyl alcohol; water / 8 h / 80 °C
  • 30
  • [ 635678-09-0 ]
  • (R)-N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)-2-(1-oxoisoindolin-2-yl)-2-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3: 2-methoxy-ethanol / 8 h / 120 °C 4: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5: hydrogenchloride / isopropyl alcohol; water / 8 h / 80 °C
  • 31
  • [ 635678-09-0 ]
  • N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)-2-(3-fluorophenyl)-2-(1-oxoisoindolin-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3: 2-methoxy-ethanol / 8 h / 120 °C 4: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5: hydrogenchloride / isopropyl alcohol; water / 8 h / 80 °C
  • 32
  • [ 635678-09-0 ]
  • N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)-2-(4-fluorophenyl)-2-(1-oxoisoindolin-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3: 2-methoxy-ethanol / 8 h / 120 °C 4: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5: hydrogenchloride / isopropyl alcohol; water / 8 h / 80 °C
  • 33
  • [ 635678-09-0 ]
  • 2-(2,5-difluorophenyl)-N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-yl)amino)phenyl)-2-(1-oxoisoindolin-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3: 2-methoxy-ethanol / 8 h / 120 °C 4: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5: hydrogenchloride / isopropyl alcohol; water / 8 h / 80 °C
  • 34
  • [ 635678-09-0 ]
  • 2-cyclohexyl-N-(3-fluoro-4-((6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline-4-yl)amino)phenyl)-2-(1-oxoisoindolin-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: nitric acid; trifluoroacetic acid / dichloromethane / 25 °C 2: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 25 °C 3: 2-methoxy-ethanol / 8 h / 120 °C 4: thionyl chloride; N,N-dimethyl-formamide / 3 h / Heating 5: hydrogenchloride / isopropyl alcohol; water / 8 h / 80 °C
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