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[ CAS No. 1246349-89-2 ] {[proInfo.proName]}

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Chemical Structure| 1246349-89-2
Chemical Structure| 1246349-89-2
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Quality Control of [ 1246349-89-2 ]

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Product Details of [ 1246349-89-2 ]

CAS No. :1246349-89-2 MDL No. :MFCD11847304
Formula : C7H5Cl2NO Boiling Point : -
Linear Structure Formula :- InChI Key :SDXMFHWBWDBSKR-UHFFFAOYSA-N
M.W : 190.03 Pubchem ID :53402442
Synonyms :

Calculated chemistry of [ 1246349-89-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.45
TPSA : 29.96 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) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 2.13
Log Po/w (WLOGP) : 2.59
Log Po/w (MLOGP) : 1.31
Log Po/w (SILICOS-IT) : 2.94
Consensus Log Po/w : 2.12

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.7
Solubility : 0.381 mg/ml ; 0.00201 mol/l
Class : Soluble
Log S (Ali) : -2.39
Solubility : 0.773 mg/ml ; 0.00407 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.6
Solubility : 0.0483 mg/ml ; 0.000254 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.56

Safety of [ 1246349-89-2 ]

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 [ 1246349-89-2 ]

* 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 [ 1246349-89-2 ]

[ 1246349-89-2 ] Synthesis Path-Downstream   1~46

  • 1
  • [ 1246349-88-1 ]
  • [ 1246349-89-2 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 1-(2,4-dichloropyridin-3-yl)ethan-1-ol With 4-methylmorpholine N-oxide In dichloromethane for 0.25h; Molecular sieve; Stage #2: With tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2h; xxii.b (b) 1-(2,4-Dichloropyridin-3-yl)ethan-1-one (I58) Freshly activated 4 A molecular sieves (3.5 g) and NMO (2.5 g, 21.2 mmol) were added to a solution of 1-(2,4-dichloropyridin-3-yl)ethan-1-ol (I57) (2.7 g, 14.1 mmol) in DCM (30 ml.) and the mixture was stirred for 15 min. TPAP (248 mg, 0.71 mmol) was added and the mixture was stirred at room temperature for 2 h. The solids were removed by filtration and the filtrate was diluted with water (100 ml.) and extracted with EtOAc (100 ml. x 3). The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Pet. Ether/EtOAc = 1 :0 to 30:1 ) to give the title compound (2.4 g, 90%) as a pale yellow oil. LCMS-C: rt 1.17 min; m/z 189.9 [M+H]+.
80% Stage #1: 1-(2,4-dichloropyridin-3-yl)ethan-1-ol With 4-methylmorpholine N-oxide In dichloromethane for 0.25h; Molecular sieves 4Å; Stage #2: With tetrapropylammonium perruthennate In dichloromethane at 20℃; for 2h; 2 Intermediate 2 1-(2,4-Dichloro-pyridin-3-yl)-ethanone Freshly activated 4A molecular sieves (9.Og) and NMO (7.1 g, 60.9 mmol) were added to a solution of Intermediate 1 (7.8 g, 40.6 mmol) in DCM (130 ml) and the mixture was stirred for 15 minutes. TPAP (403 mg, 1.15 mmol) was added and the reaction mixture was stirred for 2 hours at rt. The mixture was then filtered through Celite and the filtrate was concentrated. The crude residue was purified by flash column chromatography over silica gel (270 g) eluting with 4:1 petroleum etheϖEtOAc to give a pale yellow coloured oil (6.2 g, 80%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.62 (s, 3 H) 7.34 (d, J=5.50 Hz, 1 H) 8.34 (d, J=5.50 Hz, 1 H).
  • 2
  • [ 1246349-89-2 ]
  • [ 120422-93-7 ]
YieldReaction ConditionsOperation in experiment
64% With hydrazine hydrate at 20℃; 3 Intermediate 3 4-Chloro-3-methyl-1H-pyrazolo[4,3-c]pyridine 1-(2,4-DichIoro-pyridin-3-yl)-ethanone (6.2 g, 32.6 mmol) in 65% hydrazine monohydrate (45 ml) was stirred at rt overnight. The mixture was diluted with EtOAc and water. The organic extract was washed with brine, dried and concentrated to give a white solid. The crude product was purified by flash column chromatography over silica gel (200 g) eluting with 1:1 petroleum etherEtOAc to give an off-white solid (3.5 g, 64%). 1H NMR (400 MHz, DMSO-Cf6) δ ppm 2.64 (s, 3 H) 7.47 (d, J=5.95 Hz, 1 H) 8.06 (d, J=5.95 Hz, 1 H). m/z (ESH-APCI)+ : 168 / 170 [M+H]+.
In water at 20℃; Intermediate 31 4-Chloro-3-methyl- 1 H-pyrazolo[4, 3-c]pyridine 1-(2,4-Dichloro-pyridin-3-yl)-ethanone (6.2 g, 32.6 mmol) in 65% aqueous hydrazine (45 ml) was stirred at rt overnight. The mixture was diluted with EtOAc and water. The organic extract was washed with brine, dried and concentrated to give a white solid. The crude product was purified by flash column chromatography over silica gel (200 g) eluting with 1 :1 petroleum ether. EtOAc to give an off-white solid (3.5 g, 64%). 1H NMR (400 MHz, DMSO-c 6) d ppm 2.64 (s, 3 H), 7.47 (d, J=5.95 Hz, 1 H), 8.06 (d, J=5.95 Hz, 1 H). m/z (ES+APCI)+ : 168 / 170 [M+H]+.
  • 3
  • [ 1246349-89-2 ]
  • [ 1246347-08-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrazine / water / 20 °C 2.1: sodium hydride / 1,4-dioxane; mineral oil / 1 h / 20 °C / Sealed microwave vial 2.2: 2 h / 20 - 190 °C / Microwave irradiation
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / 20 °C 2.1: sodium hydride / 1,4-dioxane; mineral oil / 2 h / 20 °C / Microwave irradiation 2.2: 1.5 h / 180 °C / Irradiation
  • 4
  • [ 1246349-89-2 ]
  • [ 1246350-46-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrazine / water / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 2.2: 18 h / 20 °C
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 2.2: 18 h / 20 °C
  • 5
  • [ 1246349-89-2 ]
  • [ 1367874-78-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrazine / water / 20 °C 2.1: sodium hydride / 1,4-dioxane; mineral oil / 1 h / 20 °C / Sealed microwave vial 2.2: 2 h / 20 - 190 °C / Microwave irradiation 3.1: triethylamine / dmap / acetonitrile / 1 h / 20 °C
  • 6
  • [ 1246349-89-2 ]
  • [ 1367874-79-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrazine / water / 20 °C 2.1: sodium hydride / 1,4-dioxane; mineral oil / 1 h / 20 °C / Sealed microwave vial 2.2: 2 h / 20 - 190 °C / Microwave irradiation 3.1: triethylamine / dmap / acetonitrile / 1 h / 20 °C 4.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / Reflux
  • 7
  • [ 1246349-89-2 ]
  • [ 1367874-80-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrazine / water / 20 °C 2.1: sodium hydride / 1,4-dioxane; mineral oil / 1 h / 20 °C / Sealed microwave vial 2.2: 2 h / 20 - 190 °C / Microwave irradiation 3.1: triethylamine / dmap / acetonitrile / 1 h / 20 °C 4.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / Reflux 5.1: ethanol; water / 4 h / 20 °C
  • 8
  • [ 1246349-89-2 ]
  • [ 1367874-81-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: hydrazine / water / 20 °C 2.1: sodium hydride / 1,4-dioxane; mineral oil / 1 h / 20 °C / Sealed microwave vial 2.2: 2 h / 20 - 190 °C / Microwave irradiation 3.1: triethylamine / dmap / acetonitrile / 1 h / 20 °C 4.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / Reflux 5.1: ethanol; water / 4 h / 20 °C 6.1: lithium aluminium tetrahydride / diethyl ether / 20 °C / Cooling with ice 6.2: 1 h / -10 °C
  • 9
  • [ 1246349-89-2 ]
  • [ 1367874-53-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrazine / water / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C 2.2: 18 h / 20 °C 3.1: sodium t-butanolate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 18 h / 100 °C / Inert atmosphere 3.2: 18 h / 20 °C
  • 10
  • [ 1246349-89-2 ]
  • [ 1367872-50-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: hydrazine / water / 20 °C 2.1: sodium hydride / 1,4-dioxane; mineral oil / 1 h / 20 °C / Sealed microwave vial 2.2: 2 h / 20 - 190 °C / Microwave irradiation 3.1: triethylamine / dmap / acetonitrile / 1 h / 20 °C 4.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / Reflux 5.1: ethanol; water / 4 h / 20 °C 6.1: lithium aluminium tetrahydride / diethyl ether / 20 °C / Cooling with ice 6.2: 1 h / -10 °C 7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C
  • 11
  • [ 26452-80-2 ]
  • [ 1246349-89-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2.5 h / -78 °C 1.2: 1.5 h / -78 °C 2.1: tetrahydrofuran / -78 - 20 °C 3.1: 4-methylmorpholine N-oxide / dichloromethane / 0.25 h / Molecular sieves 4Å 3.2: 2 h / 20 °C
Multi-step reaction with 2 steps 1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 20 °C 2.1: 4-methylmorpholine N-oxide / dichloromethane / 0.25 h / Molecular sieve 2.2: 2 h / 20 °C
  • 12
  • [ 1246349-89-2 ]
  • [ 1246347-18-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / 20 °C 2: potassium hydroxide / water / 1 h / 120 °C / Microwave irradiation
  • 13
  • [ 1246349-89-2 ]
  • [ 1246347-15-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / 20 °C 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.08 h / Inert atmosphere 2.2: 1.67 h / 120 °C / Inert atmosphere; Microwave irradiation
  • 14
  • [ 1246349-89-2 ]
  • [ 1246347-23-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / 20 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / Inert atmosphere; Reflux 4: trifluoroacetic acid / 18 h / Reflux
  • 15
  • [ 1246349-89-2 ]
  • [ 1246347-22-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / 20 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 20 - 60 °C / Inert atmosphere 4: trifluoroacetic acid / 3 h / Reflux
  • 16
  • [ 1246349-89-2 ]
  • [ 1246346-41-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / 20 °C 2: sodium carbonate / palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,4-dioxane; water / 0.33 h / 160 °C / Microwave irradiation; Inert atmosphere
  • 17
  • [ 1246349-89-2 ]
  • [ 1246347-19-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrazine hydrate / 20 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 20 - 60 °C / Inert atmosphere
  • 18
  • [ 1246349-89-2 ]
  • [ 1246347-12-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / 20 °C 2.1: sodium hydride / 1,4-dioxane; mineral oil / 2 h / 20 °C / Irradiation 2.2: 1.5 h / 170 °C / Microwave irradiation
  • 19
  • [ 1246349-89-2 ]
  • [ 1246349-90-5 ]
  • C15H16ClN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / 20 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
  • 20
  • [ 1246349-89-2 ]
  • [ 1246346-53-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / 20 °C 2: hydrogenchloride / butan-1-ol / 0.75 h / 190 °C / Irradiation
  • 21
  • [ 1246349-89-2 ]
  • [ 1246345-95-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / 20 °C 2: butan-1-ol / 0.33 h / 190 °C / Sealed vial; Microwave irradiation
  • 22
  • [ 1246349-89-2 ]
  • [ 1246349-91-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrazine hydrate / 20 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.33 h / 180 °C / Inert atmosphere; Microwave irradiation
  • 23
  • [ 1246349-89-2 ]
  • [ 1246346-86-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / 20 °C 2.1: hydrogenchloride / butan-1-ol / 0.75 h / 190 °C / Microwave irradiation 2.2: Isolute-NH2 cartridge
  • 24
  • [ 1246349-89-2 ]
  • [ 1246347-14-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / 20 °C 2.1: sodium hydride / 1,4-dioxane; mineral oil / 2 h / 20 °C 2.2: 72 h / 90 °C
  • 25
  • [ 1246349-89-2 ]
  • [ 1246346-94-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: hydrazine hydrate / 20 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.33 h / 180 °C / Inert atmosphere; Microwave irradiation 4.1: water; potassium hydroxide / ethanol / 18 h / Reflux 4.2: pH 3 5.1: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 72 h / 20 °C 5.2: Isolute-NH2 cartridge 6.1: trifluoroacetic acid / 18 h / Reflux
  • 26
  • [ 1246349-89-2 ]
  • [ 1246349-92-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrazine hydrate / 20 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.33 h / 180 °C / Inert atmosphere; Microwave irradiation 4.1: water; potassium hydroxide / ethanol / 18 h / Reflux 4.2: pH 3
  • 27
  • [ 1246349-89-2 ]
  • [ 1246350-52-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrazine hydrate / 20 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / Inert atmosphere; Reflux
  • 28
  • [ 1246349-89-2 ]
  • [ 1246346-93-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / 20 °C 2: hydrogenchloride / butan-1-ol / 1 h / 190 °C / Microwave irradiation
  • 29
  • [ 1246349-89-2 ]
  • [ 1246346-95-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: hydrazine hydrate / 20 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / palladium diacetate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 4.1: hydrogenchloride / water / 3 h / 20 °C 5.1: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C 5.2: Isolute-NH2 cartridge 6.1: trifluoroacetic acid / 18 h / Reflux
  • 30
  • [ 1246349-89-2 ]
  • [ 1246350-51-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrazine hydrate / 20 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 20 - 60 °C / Inert atmosphere
  • 31
  • [ 1246349-89-2 ]
  • [ 1246346-91-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / 20 °C 2: butan-1-ol / 0.5 h / 190 °C / Microwave irradiation
  • 32
  • [ 1246349-89-2 ]
  • [ 1246346-92-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / 20 °C 2: butan-1-ol / 1.5 h / 190 °C / Microwave irradiation
  • 33
  • [ 1246349-89-2 ]
  • [ 1246346-98-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: hydrazine hydrate / 20 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / palladium diacetate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 4.1: hydrogenchloride / water / 3 h / 20 °C 5.1: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C 5.2: Isolute-NH2 cartridge 6.1: trifluoroacetic acid / 18 h / Reflux
  • 34
  • [ 1246349-89-2 ]
  • [ 1246347-00-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: hydrazine hydrate / 20 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / palladium diacetate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 4.1: sodium hydroxide / ethanol / 4 h / 70 °C 4.2: pH 6 5.1: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C 6.1: trifluoroacetic acid / methanol; dichloromethane / 18 h / Reflux
  • 35
  • [ 1246349-89-2 ]
  • [ 1246349-95-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrazine hydrate / 20 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / palladium diacetate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 4.1: sodium hydroxide / ethanol / 4 h / 70 °C 4.2: pH 6
  • 36
  • [ 1246349-89-2 ]
  • [ 1246349-96-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrazine hydrate / 20 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / palladium diacetate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere
  • 37
  • [ 1246349-89-2 ]
  • [ 1246350-49-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrazine hydrate / 20 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / palladium diacetate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 4.1: hydrogenchloride / water / 3 h / 20 °C 5.1: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C 5.2: Isolute-NH2 cartridge
  • 38
  • [ 1246349-89-2 ]
  • [ 1246350-48-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrazine hydrate / 20 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 0.33 h / 180 °C / Inert atmosphere; Microwave irradiation 4.1: water; potassium hydroxide / ethanol / 18 h / Reflux 4.2: pH 3 5.1: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 72 h / 20 °C 5.2: Isolute-NH2 cartridge
  • 39
  • [ 1246349-89-2 ]
  • [ 1246349-93-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrazine hydrate / 20 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / palladium diacetate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere
  • 40
  • [ 1246349-89-2 ]
  • (3-methyl-1H-pyrazolo[4,3-c]pyridin-4-yl)-(4-1,2,4-triazol-1-yl-phenyl)-amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrazine hydrate / 20 °C 2: hydrogenchloride / butan-1-ol / 0.75 h / 190 °C / Microwave irradiation
  • 41
  • [ 1246349-89-2 ]
  • C25H31N5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrazine hydrate / 20 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / palladium diacetate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 4.1: hydrogenchloride / water / 3 h / 20 °C 5.1: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C 5.2: Isolute-NH2 cartridge
  • 42
  • [ 1246349-89-2 ]
  • C27H29N5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrazine hydrate / 20 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / palladium diacetate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 4.1: sodium hydroxide / ethanol / 4 h / 70 °C 4.2: pH 6 5.1: 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C
  • 43
  • [ 1246349-89-2 ]
  • [1-(4-methoxy-benzyl)-3-methyl-1H-pyrazolo[4,3-c]pyridin-4-yl]-piperidin-4-yl-amine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / 20 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / palladium diacetate / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 4: hydrogenchloride / water / 3 h / 20 °C
  • 44
  • [ 134031-24-6 ]
  • [ 1246349-89-2 ]
  • 45
  • [ 1246349-89-2 ]
  • ethyl 3-(bromomethyl)-4-chlorothieno[3,2-c]pyridine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 50 - 70 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 3 h / Reflux
  • 46
  • [ 1246349-89-2 ]
  • [ 623-51-8 ]
  • ethyl 4-chloro-3-methylthieno[3,2-c]pyridine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate In N,N-dimethyl-formamide at 50 - 70℃; xxii.c (c) Ethyl 4-chloro-3-methylthieno[3,2-c]pyridine-2-carboxylate (I59) A suspension of 1-(2,4-dichloropyridin-3-yl)ethan-1-one (I58) (400 mg, 2.12 mmol), ethyl 2- mercaptoacetate (255 mg, 2.12 mmol) and K2CO3 (440 mg, 3.18 mmol) in DMF (15 mL) was heated at 50 °C for 12 h and then at 70 °C overnight. Water (100 mL) was added and the mixture was extracted with EtOAc (50 mL c 3). The combined organic extracts were washed with water (100 mL x 3), brine (100 mL), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Pet. Ether/EtOAc = 1 :0 to 100:1 ) to give the title compound (500 mg, 92%) as a white solid. LCMS-C: rt2.42 min; m/z 255.9 [M+H]+.
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