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[ CAS No. 106976-24-3 ] {[proInfo.proName]}

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Product Details of [ 106976-24-3 ]

CAS No. :106976-24-3 MDL No. :MFCD12026295
Formula : C8H8BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PJGDLDZLEKENNP-UHFFFAOYSA-N
M.W : 230.06 Pubchem ID :13792251
Synonyms :

Calculated chemistry of [ 106976-24-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 50.47
TPSA : 63.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 2.37
Log Po/w (WLOGP) : 2.05
Log Po/w (MLOGP) : 0.95
Log Po/w (SILICOS-IT) : 1.64
Consensus Log Po/w : 1.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.199 mg/ml ; 0.000864 mol/l
Class : Soluble
Log S (Ali) : -3.34
Solubility : 0.105 mg/ml ; 0.000457 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.66
Solubility : 0.504 mg/ml ; 0.00219 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.45

Safety of [ 106976-24-3 ]

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 [ 106976-24-3 ]

* 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 [ 106976-24-3 ]

[ 106976-24-3 ] Synthesis Path-Downstream   1~47

  • 1
  • [ 106976-23-2 ]
  • [ 106976-24-3 ]
YieldReaction ConditionsOperation in experiment
~ 60% A 30% hydrogen peroxide sol. (2 mL/g) was added to a sol. of isatin derivative in 10 M of sodium hydroxide sol. (10 mL/g) at 70 C. and the reaction mixture was then held at this temperature for 1 h. The mixture was then cooled to 0 C., adjusted to pH 8 with conc. HCl, diluted with EE and then brought to pH 4-5. The organic phase was washed with water, dried (NaSO4) and the solvent removed. (Yield approx. 60%)
  • 2
  • [ 106976-24-3 ]
  • [ 108-24-7 ]
  • [ 106976-25-4 ]
YieldReaction ConditionsOperation in experiment
94% In acetic acid at 100℃; for 0.25h;
With acetic acid at 90 - 95℃; for 0.166667h;
  • 3
  • [ 6933-10-4 ]
  • [ 106976-24-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 80 percent / hydroxylamine sulfate, sodium sulfate, aq. HCl / 8 h / 80 °C 2: 33 percent / aq. H2SO4 / 0.25 h / 80 °C 3: 86 percent / 3percent NaOH, 27percent aq. H2O2
  • 4
  • [ 106976-24-3 ]
  • [ 34545-25-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 94 percent / acetic acid / 0.25 h / 100 °C 2: 64 percent / HNO3 / 0.25 h / 0 - 5 °C 3: 71 percent / 50percent aq. H2SO4 / 5 h / 100 °C 4: H2, NaOH / Pd/C / H2O
Multi-step reaction with 4 steps 1: AcOH / 0.17 h / 90 - 95 °C 2: fuming HNO3 / 0.17 h / 5 °C 3: aq. NaOH / 5 h / 90 °C 4: H2, aq. NaOH / Pd/C
  • 5
  • [ 106976-24-3 ]
  • [ 106976-27-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 94 percent / acetic acid / 0.25 h / 100 °C 2: 64 percent / HNO3 / 0.25 h / 0 - 5 °C 3: 71 percent / 50percent aq. H2SO4 / 5 h / 100 °C
Multi-step reaction with 3 steps 1: AcOH / 0.17 h / 90 - 95 °C 2: fuming HNO3 / 0.17 h / 5 °C 3: aq. NaOH / 5 h / 90 °C
  • 6
  • [ 106976-24-3 ]
  • [ 106976-26-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 94 percent / acetic acid / 0.25 h / 100 °C 2: 64 percent / HNO3 / 0.25 h / 0 - 5 °C
Multi-step reaction with 2 steps 1: AcOH / 0.17 h / 90 - 95 °C 2: fuming HNO3 / 0.17 h / 5 °C
  • 7
  • [ 106976-24-3 ]
  • [ 106976-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 94 percent / acetic acid / 0.25 h / 100 °C 2: 64 percent / HNO3 / 0.25 h / 0 - 5 °C 3: 71 percent / 50percent aq. H2SO4 / 5 h / 100 °C 4: H2, NaOH / Pd/C / H2O 5: methanol / 0.25 h / Heating
  • 8
  • [ 106976-24-3 ]
  • [ 106976-14-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 94 percent / acetic acid / 0.25 h / 100 °C 2: 64 percent / HNO3 / 0.25 h / 0 - 5 °C 3: 71 percent / 50percent aq. H2SO4 / 5 h / 100 °C 4: H2, NaOH / Pd/C / H2O 5: methanol / 0.25 h / Heating 6: 5percent Pd/C / various solvent(s) / 72 h / Heating
  • 9
  • [ 106987-81-9 ]
  • [ 106976-24-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 33 percent / aq. H2SO4 / 0.25 h / 80 °C 2: 86 percent / 3percent NaOH, 27percent aq. H2O2
  • 10
  • [ 106976-24-3 ]
  • [ 124340-99-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: AcOH / 0.17 h / 90 - 95 °C 2: fuming HNO3 / 0.17 h / 5 °C 3: aq. NaOH / 5 h / 90 °C 4: H2, aq. NaOH / Pd/C 5: cupric acetate, AcOH / H2O; methanol / Heating
  • 11
  • [ 106976-24-3 ]
  • [ 124340-71-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: AcOH / 0.17 h / 90 - 95 °C 2: fuming HNO3 / 0.17 h / 5 °C 3: aq. NaOH / 5 h / 90 °C 4: H2, aq. NaOH / Pd/C 5: cupric acetate, AcOH / H2O; methanol / Heating 6: 1.) 1,1'-carbonyldiimidazole / 1.) DMF, 40 deg C, 5 min, 2.) 10 min
  • 12
  • [ 106976-24-3 ]
  • [ 60100-09-6 ]
  • [ 943605-85-4 ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: 2-amino-5-bromo-4-methylbenzoic acid With ammonia for 1h; Heating / reflux; Stage #2: formamide for 4h; Heating / reflux; Stage #3: With water for 0.5h; Heating / reflux; v; 1 The bromoanthranilic acid (commercially available or produced as described above) was refluxed for 1 hour in liquid ammonia (1 mL/g). The solution was then evaporated to low bulk and the residue mixed with formamide (2 mL/g) and refluxed 4 hours. Water was added, the mixture boiled for 30 min, and 20% sodium hydroxide sol. was then added until a clear solution formed. Ammonium carbonate was added to the hot solution until a precipitate formed. The mixture was held at 4° C. for 16 hours before the precipitate was filtered out, washed with water and dried in vacuum (yield 50-80%).
  • 13
  • [ 64818-80-0 ]
  • [ 106976-24-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: acetic acid; bromine / 120 h / 20 °C 3: sodium hydroxide; water / 20 h / 90 °C
  • 14
  • [ 2305-36-4 ]
  • [ 106976-24-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sulfuric acid / 67 h / Reflux 2: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 3: acetic acid; bromine / 120 h / 20 °C 4: sodium hydroxide; water / 20 h / 90 °C
9.04 g With hydrogen bromide In water; dimethyl sulfoxide at 10 - 35℃; 10.A A) 2-amino-5-bromo-4-methylbenzoic acid To a mixture of 2-amino-4-methylbenzoic acid (6.14 g) and DMSO (60 mil) was added hydrobromic acid (48% v/v, 23 mL) at 0°C, and the mixture was stirred at room temperature overnight. To the reaction mixture was added water (150 mL) and the mixture was stirred for 30 min. The precipitate was collected by filtration, washed with water and dried to give the title compound (9.04 g) . (1428) MS, found: 230.0, 232.0.
YieldReaction ConditionsOperation in experiment
With water; sodium hydroxide In ethanol at 60℃; for 1h; 67 2-Amino-3-chloro-4-formyl-5-trifluoromethyl-benzoic acid General procedure: A 1 N aqueous sodium hydroxide solution (23 ml) was added to a solution of 2-amino-3-chloro-4-formyl-5-trifluoromethyl-benzoic acid ethyl ester (Compound 24, 3.47 g, 12 mmol) in ethanol (117 ml), and the mixture was stirred at 60°C for one hour. After cooling to room temperature, a 1 N aqueous hydrochloric acid solution (23 ml) was added, and the reaction solution was concentrated under reduced pressure to give a crude product of the title compound. LCMS: m/z 266 [M-H]- HPLC retention time: 0.67 min (analysis condition D)
With N-Bromosuccinimide In N,N-dimethyl-formamide at -10℃; for 2h;
  • 16
  • [ 79043-90-6 ]
  • [ 106976-24-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; bromine / 120 h / 20 °C 2: sodium hydroxide; water / 20 h / 90 °C
  • 17
  • ethyl 2-acetamido-5-bromo-4-methylbenzoate [ No CAS ]
  • [ 106976-24-3 ]
YieldReaction ConditionsOperation in experiment
81% With water; sodium hydroxide at 90℃; for 20h;
  • 18
  • [ 106976-24-3 ]
  • 6-bromo-3-((1S,2S)-2-hydroxycyclohexyl)-7-methylquinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2: 4 h / 120 - 150 °C / Microwave irradiation; Sealed tube
  • 19
  • [ 106976-24-3 ]
  • 6-[(6-chloropyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclohexyl]-7-methylquinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2.1: 4 h / 120 - 150 °C / Microwave irradiation; Sealed tube 3.1: bis(tri-t-butylphosphine)palladium(0) / tetrahydrofuran / 0 °C / Inert atmosphere 3.2: 0 - 20 °C / Inert atmosphere
  • 20
  • [ 106976-24-3 ]
  • 3-[(1S,2S)-2-hydroxycyclohexyl]-7-methyl-6-[6-(1-methyl-1H-pyrazol-4-yl)pyridin-3-yl]methyl}quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 2.1: 4 h / 120 - 150 °C / Microwave irradiation; Sealed tube 3.1: bis(tri-t-butylphosphine)palladium(0) / tetrahydrofuran / 0 °C / Inert atmosphere 3.2: 0 - 20 °C / Inert atmosphere 4.1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 2 h / 100 °C / Microwave irradiation; Sealed tube; Inert atmosphere
  • 21
  • [ 106976-24-3 ]
  • [ 13374-30-6 ]
  • 2-amino-5-bromo-N-((1S,2S)-2-hydroxycyclohexyl)-4-methylbenzamide [ No CAS ]
  • 22
  • [ 67-56-1 ]
  • [ 106976-24-3 ]
  • methyl 2-amino-5-bromo-4-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride at 0 - 80℃; for 24h; Experimental procedure for the synthesis of A-9a A-6c (5.0 g, 21 .7 mmol, 1.0 equiv.) is dissolved in MeOH (50 mL) and cooled down to 0 °C. Thionyl chloride (12.9 g, 108.7 mmol, 5.0 equiv.) is added dropwise, then the reaction mixture is stirred for 24 h at 80 °C. MeOH is evaporated, water is added to the reaction mixture and extracted with EtOAc. The combined organic layer is dried (MgS04), filtered and concentrated in vacuo to give product A-9a (HPLC method: GVK_LCMS_05: tret [min] = 1 .67; [M+H]+ = 196.1 ).
  • 23
  • [ 106976-24-3 ]
  • C10H8BrClN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonium acetate / methanol / 24 h / 120 °C / Sealed tube 2: trichlorophosphate / 4 h / 140 °C
  • 24
  • [ 1445-45-0 ]
  • [ 106976-24-3 ]
  • C10H9BrN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate In methanol at 120℃; for 24h; Sealed tube; Experimental procedure for the synthesis of Α-10i To a stirred solution of A-6b (75.0 g, 326.0 mmol, 1 .0 equiv.) in MeOH (600 mL) is added ammonium acetate (251.0 g, 3.3 mol, 10.0 equiv.) and trimethyl orthoacetate (391.2 g, 3.3 mol, 10.0 equiv.). The reaction mixture is heated in a seal tube to 120 °C for 24 h. The MeOH is evaporated, water is added to the reaction mixture and the precipitate is filtered off. The crude compound is washed with petrol ether and Et20 to give the desired product Α-10i.
  • 25
  • [ 106976-24-3 ]
  • 1,5-anhydro-3-(6-bromo-8-chloro-7-methyl-4-oxo-1,2,3-benzotriazin-3(4H)-yl)-2,3-dideoxy-L-threo-pentitol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-chloro-succinimide / acetonitrile / 10 - 35 °C 2: HATU; triethylamine / N,N-dimethyl-formamide / 10 - 35 °C 3: hydrogenchloride; sodium nitrite / water / 3 h / 0 - 35 °C
  • 26
  • [ 106976-24-3 ]
  • 1,5-anhydro-3-(8-chloro-7-methyl-4-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3-benzotriazin-3(4H)-yl)-2,3-dideoxy-L-threo-pentitol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-chloro-succinimide / acetonitrile / 10 - 35 °C 2: HATU; triethylamine / N,N-dimethyl-formamide / 10 - 35 °C 3: hydrogenchloride; sodium nitrite / water / 3 h / 0 - 35 °C 4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 110 °C / Inert atmosphere
  • 27
  • [ 106976-24-3 ]
  • 1,5-anhydro-3-(8-chloro-6-(3-fluoro-4-(methylcarbamoyl)benzyl)-7-methyl-4-oxoquinazolin-3(4H)-yl)-2,3-dideoxy-L-threo-pentitol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-chloro-succinimide / acetonitrile / 10 - 35 °C 2: HATU; triethylamine / N,N-dimethyl-formamide / 10 - 35 °C 3: 2 h / 90 °C / Inert atmosphere 4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 110 °C / Inert atmosphere 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 1 h / 100 °C / Microwave irradiation
  • 28
  • [ 106976-24-3 ]
  • 2-amino-5-bromo-3-chloro-4-methylbenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.59 g With N-chloro-succinimide In acetonitrile at 10 - 35℃; 10.B B) 2-amino-5-bromo-3-chloro-4-methylbenzoic acid To a mixture of 2-amino-5-bromo-4-methylbenzoic acid (1432) (9.04 g) and acetonitrile (180 mL) was added NCS (7.35 g) at room temperature. The mixture was stirred at room temperature overnight. The precipitate was collected by filtration, washed with a small amount of ethyl acetate and dried under reduced pressure to give the title compound (5.59 g) . MS, found: 264.0, 266.0.
  • 29
  • [ 106976-24-3 ]
  • 3-((2-amino-5-bromo-3-chloro-4-methylbenzoyl)amino)-1,5-anhydro-2,3-dideoxy-L-threo-pentitol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-chloro-succinimide / acetonitrile / 10 - 35 °C 2: HATU; triethylamine / N,N-dimethyl-formamide / 10 - 35 °C
  • 30
  • [ 106976-24-3 ]
  • 1,5-anhydro-3-(6-bromo-8-chloro-7-methyl-4-oxoquinazolin-3(4H)-yl)-2,3-dideoxy-L-threo-pentitol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-chloro-succinimide / acetonitrile / 10 - 35 °C 2: HATU; triethylamine / N,N-dimethyl-formamide / 10 - 35 °C 3: 2 h / 90 °C / Inert atmosphere
  • 31
  • [ 106976-24-3 ]
  • 1,5-anhydro-3-(8-chloro-7-methyl-4-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-3(4H)-yl)-2,3-dideoxy-L-threo-pentitol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-chloro-succinimide / acetonitrile / 10 - 35 °C 2: HATU; triethylamine / N,N-dimethyl-formamide / 10 - 35 °C 3: 2 h / 90 °C / Inert atmosphere 4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 110 °C / Inert atmosphere
  • 32
  • [ 106976-24-3 ]
  • 1,5-anhydro-3-(8-chloro-6-(3-fluoro-4-(methylcarbamoyl)benzyl)-7-methyl-4-oxo-1,2,3-benzotriazin-3(4H)-yl)-2,3-dideoxy-L-threo-pentitol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-chloro-succinimide / acetonitrile / 10 - 35 °C 2: HATU; triethylamine / N,N-dimethyl-formamide / 10 - 35 °C 3: hydrogenchloride; sodium nitrite / water / 3 h / 0 - 35 °C 4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene / 110 °C / Inert atmosphere 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 1 h / 100 °C
  • 33
  • [ 106976-24-3 ]
  • methyl 6-bromo-5-methylquinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid; nitrobenzene / 16 h / 125 °C 2: thionyl chloride / 16 h / 0 °C / Reflux
  • 34
  • [ 106976-24-3 ]
  • methyl 5-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sulfuric acid; nitrobenzene / 16 h / 125 °C 2.1: thionyl chloride / 16 h / 0 °C / Reflux 3.1: potassium acetate / 1,4-dioxane / 0.25 h / 25 - 30 °C / Inert atmosphere 3.2: 10 h / 100 °C / Inert atmosphere
  • 35
  • [ 106976-24-3 ]
  • methyl 6-(2-chloropyridin-4-ylmethyl)-5-methylquinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sulfuric acid; nitrobenzene / 16 h / 125 °C 2.1: thionyl chloride / 16 h / 0 °C / Reflux 3.1: potassium acetate / 1,4-dioxane / 0.25 h / 25 - 30 °C / Inert atmosphere 3.2: 10 h / 100 °C / Inert atmosphere 4.1: potassium carbonate / water; 1,4-dioxane / 0.25 h / 25 - 30 °C / Inert atmosphere 4.2: 8 h / 100 °C / Inert atmosphere
  • 36
  • [ 106976-24-3 ]
  • 6-(2-chloropyridin-4-ylmethyl)-5-methylquinoline-8-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sulfuric acid; nitrobenzene / 16 h / 125 °C 2.1: thionyl chloride / 16 h / 0 °C / Reflux 3.1: potassium acetate / 1,4-dioxane / 0.25 h / 25 - 30 °C / Inert atmosphere 3.2: 10 h / 100 °C / Inert atmosphere 4.1: potassium carbonate / water; 1,4-dioxane / 0.25 h / 25 - 30 °C / Inert atmosphere 4.2: 8 h / 100 °C / Inert atmosphere 5.1: sodium hydroxide; water / methanol / 2 h / 0 °C / Reflux
  • 37
  • [ 106976-24-3 ]
  • N-(2-hydroxycyclohexyl)-6-(2-chloropyridin-4-ylmethyl)-5-methylquinoline-8-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sulfuric acid; nitrobenzene / 16 h / 125 °C 2.1: thionyl chloride / 16 h / 0 °C / Reflux 3.1: potassium acetate / 1,4-dioxane / 0.25 h / 25 - 30 °C / Inert atmosphere 3.2: 10 h / 100 °C / Inert atmosphere 4.1: potassium carbonate / water; 1,4-dioxane / 0.25 h / 25 - 30 °C / Inert atmosphere 4.2: 8 h / 100 °C / Inert atmosphere 5.1: sodium hydroxide; water / methanol / 2 h / 0 °C / Reflux 6.1: N-ethyl-N,N-diisopropylamine; O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate / dichloromethane / 16 h / 0 - 30 °C
  • 38
  • [ 106976-24-3 ]
  • [ 56-81-5 ]
  • 6-bromo-5-methylquinoline-8-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With sulfuric acid; nitrobenzene at 125℃; for 16h; Intermediate 1: 6-Bromo-5-methylquinoline-8-carboxylic acid (I-i) To a stirred solution of 2-amino-5-bromo-4-methyl-benzoic acid (15.9 g, 69.1 mmol) in nitrobenzene (22.8 mL) at RT, glycerol (24.8 g, 269.6 mmol) followed by con. H2SO4 (22.28 g, 222.8 mmol) were added. Reaction mixture was gradually heated to 125 °C and was stirred at this temperature for 16 h. After cooling it to RT, the reaction mixture was quenched with ice & diluted with water and EtOAc. The two layers were separated and aqueous layer was extracted with EtOAc. The aqueous layer was further extracted with 10% ammonical methanol DCM solvent system. The combined organic layer was washed once with brine solution, dried over anhydrous Na2S04 and the solvent was removed under reduced pressure to obtain the title compound. Yield: 9.65 g (52 %); 1H-NMR (400 MHz, CDC13): δ 16.49 (bs, 1H), 8.94 (s, 1H), 8.93 (d, 7=6.2 Hz, 1H), 7.69 (dd, 7=4.3, 8.6 Hz, 1H), 2.87 (s, 3H); Mass (m z): 265.8, 267.8 (M+H)+.
  • 40
  • [ 106976-24-3 ]
  • C16H21N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / 60 °C / Inert atmosphere 2: ammonium hydroxide / water / Reflux 3: potassium phosphate; <i>L</i>-proline; copper(l) iodide / dimethyl sulfoxide / 90 °C / Inert atmosphere; Sealed tube
  • 41
  • [ 106976-24-3 ]
  • C24H26BrN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / 60 °C / Inert atmosphere 2: ammonium hydroxide / water / Reflux 3: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 25 °C
  • 42
  • [ 106976-24-3 ]
  • C32H46N4O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine / 60 °C / Inert atmosphere 2: ammonium hydroxide / water / Reflux 3: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 25 °C 4: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 16 h / Inert atmosphere; Reflux
  • 43
  • [ 106976-24-3 ]
  • C33H48N4O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: pyridine / 60 °C / Inert atmosphere 2: ammonium hydroxide / water / Reflux 3: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 25 °C 4: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 16 h / Inert atmosphere; Reflux 5: sodium cyanoborohydride; sodium tris(acetoxy)borohydride / methanol; water / 1 h / 20 °C
  • 44
  • [ 106976-24-3 ]
  • {2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-7-methylquinazolin-6-yl}-N-methyl-N-propylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine / 60 °C / Inert atmosphere 2: ammonium hydroxide / water / Reflux 3: potassium phosphate; <i>L</i>-proline; copper(l) iodide / dimethyl sulfoxide / 90 °C / Inert atmosphere; Sealed tube 4: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C
  • 45
  • [ 106976-24-3 ]
  • 2-({2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-7-methylquinazolin-6-yl}-N-methylamino)ethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: pyridine / 60 °C / Inert atmosphere 2: ammonium hydroxide / water / Reflux 3: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 25 °C 4: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate / toluene / 16 h / Inert atmosphere; Reflux 5: sodium cyanoborohydride; sodium tris(acetoxy)borohydride / methanol; water / 1 h / 20 °C 6: hydrogenchloride / methanol; water / 20 °C
  • 47
  • C8H9ClIN [ No CAS ]
  • [ 106976-24-3 ]
  • C16H16BrClN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
59.9% With potassium acetate; copper diacetate; copper In water at 120℃; Inert atmosphere; 18.1 Step 1: A mixture of a (1.0 g, 4.35 mmol, 1.0 eq), b (1.83 g, 6.53 mmol, 1.5 eq), potassium Acetate (1.28 g, 13.1 mmol, 3.0 eq), cupric acetate (0.24 g, 1.31 mmol, 0.3 eq), and copper powder (0.084 g, 1.31 mmol, 0.3 eq) in 2-Pentanol (20 mL) was stirred at 120 °C overnight under nitrogen atmosphere, then cooled to room temperature. Water (30 mL) was added. The mixture was filtered through celite. The filtrate was acidified to pH=2 with 2 N HCl (aq.), then water (50.0 mL) was added. The resulting mixture was extracted with EtOAc (50 mL x 2). The combined organic layers were washed with brine (50.0 mL x 2), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford the crude which was purified by trituration with PE (20 mL) to afford c 1.0 g, 59.9 %). LCMS: 383.0 [M+H]+.
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