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[ CAS No. 571189-23-6 ] {[proInfo.proName]}

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Chemical Structure| 571189-23-6
Chemical Structure| 571189-23-6
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Product Details of [ 571189-23-6 ]

CAS No. :571189-23-6 MDL No. :MFCD11849292
Formula : C14H22N4O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ICNBTOYLGTVUCE-UHFFFAOYSA-N
M.W : 278.35 Pubchem ID :75481723
Synonyms :

Calculated chemistry of [ 571189-23-6 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.57
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 85.84
TPSA : 71.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.5
Log Po/w (XLOGP3) : 1.29
Log Po/w (WLOGP) : 0.97
Log Po/w (MLOGP) : 0.98
Log Po/w (SILICOS-IT) : 0.4
Consensus Log Po/w : 1.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.34
Solubility : 1.28 mg/ml ; 0.00461 mol/l
Class : Soluble
Log S (Ali) : -2.4
Solubility : 1.12 mg/ml ; 0.00402 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.35
Solubility : 1.26 mg/ml ; 0.00452 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.66

Safety of [ 571189-23-6 ]

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 [ 571189-23-6 ]

* 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 [ 571189-23-6 ]

[ 571189-23-6 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 107-20-0 ]
  • [ 571189-23-6 ]
  • [ 684223-66-3 ]
YieldReaction ConditionsOperation in experiment
83% With sodium hydrogencarbonate In ethanol; water for 3h; Heating;
  • 2
  • [ 19798-80-2 ]
  • [ 57260-71-6 ]
  • [ 571189-23-6 ]
YieldReaction ConditionsOperation in experiment
83% In ethanol for 7h; Heating;
223 mg In N,N-dimethyl acetamide at 190℃; for 0.166667h; 19.1 Step 1: preparation of tert-butyl 4-(2-amino-4-pyridyl)piperazine-1-carboxylate (compound 19b) A mixture of 4-chloropyridin-2-amine (compound 19a, CAS: 19798-80-2, Vendor: Aldrich, 129 mg, 1.00 mmol) and te rt- butyl piperazine- 1-carboxy late (CAS: 57260-71-6, Vendor: Accela ChemBio Inc, 186 mg, 1.00 mmol) in N,N-dimethylacetamide (3 mL) was heated at 190 °C for 10 minutes. After the reaction mixture was cooled down, the solid was collected by filtration to give compound 19b (223 mg) as a grey solid. MS: calc'd 279 (MH+), measured 279 (MH+).
  • 3
  • [ 571189-23-6 ]
  • 2-bromo-1-(5-chloro-2,4-dimethoxyphenyl)ethanone [ No CAS ]
  • tert-butyl 4-(2-(5-chloro-2,4-dimethoxyphenyl)imidazo[1,2-a]pyridin-7-yl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 90℃; for 2h; 232 Preparation of tert-butyl 4-(2-(5-chloro-2,4-dimethoxyphenyl)imidazo[1,2-a]pyridin-7-yl)piperazine-1-carboxylate 11 (Example 232) A mixture of 2-bromo-1-(5-chloro-2,4-dimethoxyphenyl)ethanone 3 (2.50 g, 8.49 rnmol), tert-butyl 4-(2-arninopyridin-4-yl)piperazine-1-carboxylate 10 (226 g, 809 mmol), and NaHCO3 (1.36 g, 16.18 mmol) in DMF (5 mL) was heated at 90°C for 2 h.The reaction mixture was cooled to room temperature and poured into water. The precipitate obtained was collected by filtration and washed with water, and dried under reduced pressure. The crude material was purified by column chromatography (silica gel,4% MeOH/DCM) to provide tert-butyl 4-[2-(5-chloro-2,4-dirnethoxyphenyl)imidazo[1,2-a]pyridin-7-ylpiperazine-1-carboxylate 11 (2.3 g, 60%) as a light yellow solid. 1H NMR (300 MHz, CDCl3): δ 836 (s, 1H), 7.90 (d, J = 7.5Hz, 1H), 7.88 (s, 1H),681 (d.J= 1.8 Hz, 1H), 658 (s, 1H), 6.54 (dd,J 2.3, 7.5Hz, 1 H), 3.99 (s. 3H), 3.95 (s,3 H), 3.60 (t, J= 49Hz, 4H), 3.18 (t, J= 5.2Hz, 4H), 1.49 (s, 9H); HPLC (Method 1) 96.6% (AUC), tR= 11.55 min; ESI MS m/z 473 [M + H]+.
  • 4
  • [ 571189-23-6 ]
  • 6-bromo-2-(5-chloro-2,4-dimethoxyphenyl)-7-(piperazin-1-yl)imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2: sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 80 °C 3: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C 4: ammonium hydroxide / 1 h / 20 °C
  • 5
  • [ 571189-23-6 ]
  • tert-butyl 4-[2-(5-chloro-2-hydroxy-4-methoxyphenyl)imidazo[1,2-a]pyridin-7-yl]piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetone / 16 h / 75 °C 2: hydrogen; palladium on activated charcoal / tetrahydrofuran / 6 h / 20 °C / 760.05 Torr
  • 6
  • [ 571189-23-6 ]
  • tert-butyl 4-(2-{5-chloro-2-[3-(dimethylamino)propoxy]-4-methoxyphenyl}imidazo[1,2-a]pyridin-7-yl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetone / 16 h / 75 °C 2: hydrogen; palladium on activated charcoal / tetrahydrofuran / 6 h / 20 °C / 760.05 Torr 3: sodium t-butanolate / <i>tert</i>-butyl alcohol / 4 h / 90 °C
  • 7
  • [ 571189-23-6 ]
  • 3-{4-chloro-5-methoxy-2-[7-(piperazin-1-yl)imidazo[1,2-a]pyridin-2-yl]phenoxy}-N,N-dimethylpropan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetone / 16 h / 75 °C 2: hydrogen; palladium on activated charcoal / tetrahydrofuran / 6 h / 20 °C / 760.05 Torr 3: sodium t-butanolate / <i>tert</i>-butyl alcohol / 4 h / 90 °C 4: hydrogenchloride / 1,4-dioxane / 1 h / 50 °C
  • 8
  • [ 571189-23-6 ]
  • tert-butyl 4-(2-amino-5-bromopyridin-4-yl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 0.5h; Preparation of tert-butyl 4-(2-amino-5-bromopyridin-4-yl)piperazine-1-carboxylate 123 To a solution of tert-butyl 4-(2-aminopyridin-4-yl)piperazine-1-carboxylate 122 (250 mg, 0,90 mmol) in DMF (5 mL) was added N-bromosuccinimide (160 mg, 0.90 mmol). The reaction mixture was stirred at room temperature for 30 min. The reaction mixture was quenched with 10% sodium thiosulfate solution (100 mL) and extracted with chloroform (100 mL). The organic layer was concentrated under reduced pressure, and purified by column chromatography (silica gel, MeOH/DCM) to provide the desired compound iert-hutyi 4-(2-amino-5-bromopyridin-4-yl)piperazine-1-carboxylate 123 (150 mg, 47%) as a pale-yellow solid.
  • 9
  • [ 571189-23-6 ]
  • tert-butyl 4-[6-bromo-2-(5-chloro-2,4-dimethoxyphenyl)imidazo[1,2-a]pyridin-7-yl]piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2: sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 80 °C
  • 10
  • [ 571189-23-6 ]
  • 6-bromo-2-(5-chloro-2,4-dimethoxyphenyl)-7-(piperazin-1-yl)imidazo[1,2-a]pyridine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 20 °C 2: sodium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 80 °C 3: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C
  • 11
  • [ 571189-23-6 ]
  • 1-[2-(benzyloxy)-5-chloro-4-methoxyphenyl]-2-bromoethan-1-one [ No CAS ]
  • tert-butyl 4-{2-[2-(benzyloxy)-5-chloro-4-methoxyphenyl]imidazo[1,2-a]pyridin-7-yl}piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% In acetone at 75℃; for 16h; Preparation of tert-butyl 4-{2-[2-(benzyloxy)-5-chloro-4-methoxyphenyl]imidazo[1,2-a]pyridin-7-yl}piperazine-1-carboxylate 31 A solution of 1-[2-(benzvloxy)-5-chloro-4-rnethoxyphenyl]-2-bromoethanone 30 (132 mg, 0.359 rnrnol) and tert-butyl 4-(2-aminopyridin-4-yl)piperazine- 1-carboxylate 10 (100 rng, 0.359 mmoi) in acetone (2 mL) was heated at 75°C for 16 h. The reaction mixture was cooled to room temperature; the white precipitate was collected by filtration and washed with acetone. The solid was suspended in aqueous ammonia (10 rnL) and stirred for 2 h. The reaction mixture was filtered and dried under reduced pressure to give the desired compound tert-butyl 4-{2-[2-(benzyloxy)-5-chloro-4-methoxyphenyl]imidazo[1 ,2-a]pyridin-7-yl}piperazine-1-carboxylate 31(140 mg, 71 %) as a white solid. 1H NMR (300 MHz, CD3OD): δ 8.30 (d, J= 7.7 Hz, 1H), 7.99 (s, 1H), 7.77 (s, 1H), 7.52-7.46 (m, 2H), 7.45-7.31 (m, 3H), 7.15 (m. 1H). 6.69 (s, 1H). 6.79-6.74 (m, 1H), 5.40 (s, 2H), 390 (s, 3H), 3.67-3.51 (m, 8H), 1.49 (s. 9H); HPLC (Method 3) >99% (AUC). 6 =19.63 min.; ESI MS m/z 549 [M +H]+
  • 12
  • [ 571189-23-6 ]
  • 2-bromo-1-(5-chloro-2-ethyl-4-methoxyphenyl)ethanone [ No CAS ]
  • tert-butyl 4-[2-(5-chloro-2-ethyl-4-methoxyphenyl)imidazo[1,2-a]pyridin-7-yl]piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.4% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 90℃; for 2h; Preparation of tert-butyl 4-(2-(5-chloro-2-ethyl-4-methoxyphenyl)imidazo[l,2-a]pyridin-7-yl)piperazine-1 -carboxylate 104; A mixture of 2-bromo-1-(5-chloro-2-ethyl-4-methoxyphenyl)ethanone 103 (260 mg, 0.9()mmoi), tert-butyl 4-(2-aminopyridin-4-yl)piperazine-l-carboxylate (250 g, 0.90 mmol), and NaHCO3 (230 mg, 2.70 mmol) in DMF (5 mL) was heated at 90°C for 2 h. The reaction mixture was cooled to room temperature and poured into water. The precipitate so obtained was filtered, washed with water, and dried under reduced pressure. The precipitate was purified by column chromatography (silica gel, MeOH/DCM) to provide tert-butyl 4-(2-(5-chloro-2-ethyl-4-methoxyphenyl)imidazo[1,2-a]pyridin-7-yl)piperazine-1 -carboxylate 104 (300 mg, 71.4%) as a pale yellow solid.
  • 13
  • [ 571189-23-6 ]
  • 2-(4-fluoro-3-(trifluoromethyl)phenyl)-N-(4-(piperazin-1-yl)pyridin-2-yl)-1H-imidazo[4,5-c]pyridin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine / <i>tert</i>-butyl alcohol; toluene / 110 °C / Inert atmosphere 2: trifluoroacetic acid / neat (no solvent) / 12 h / 100 °C
  • 14
  • [ 571189-23-6 ]
  • 6-chloro-2-(4-fluoro-3-(trifluoromethyl)phenyl)-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine [ No CAS ]
  • C35H35F4N7O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; caesium carbonate In toluene; <i>tert</i>-butyl alcohol at 110℃; Inert atmosphere;
  • 16
  • [ 57260-71-6 ]
  • [ 571189-23-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / ethanol / 36 h / 60 °C 2: acetic acid; palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C
  • 17
  • 4-fluoro-2-nitropyridine [ No CAS ]
  • [ 571189-23-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / ethanol / 36 h / 60 °C 2: acetic acid; palladium on activated charcoal; hydrogen / methanol / 4 h / 25 °C
  • 18
  • [ 571189-23-6 ]
  • ((2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl)methyl trifluoromethanesulfonate [ No CAS ]
  • 5-[(2S,6R)-2-[[4-(2-amino-4-pyridyl)piperazin-1-yl]methyl]-6-methylmorpholin-4-yl]quinoline-8-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
16 mg Stage #1: tert-butyl 4-(2-aminopyridin-4-yl)piperazine-1-carboxylate With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Stage #2: ((2R,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl)methyl trifluoromethanesulfonate With potassium carbonate In acetonitrile at 85℃; for 2h; 19.2 Step 2: preparation of 5-[(2S,6R)-2-[[4-(2-amino-4-pyridyl)piperazin-1-yl]methyl]-6-methyl-morpholin-4-yl]quinoline-8-carbonitrile (Example 19) The mixture of tert-butyl 4-(2-amino-4-pyridyl)piperazine-1-carboxylate (compound 19b, 67 mg, 240 m mol) and DCM/TFA=l/2 (3 mL) was stirred at room temperature for 1 h, then it was concentrated and the residue was dissolved in ACN (6 mL), to which K2CO3 (83 mg, 600 m mol) and [(2R,6R)-4-(8-cyano-5-quinolyl)-6-methyl-morpholin-2-yl]methyl trifluoromethanesulfonate (Intermediate A, 83 mg, 200 miho) were added. After being stirred at 85 °C for 2 hrs, the reaction mixture was filtered and then directly purified by prep-HPLC to give Example 19 (16 mg). MS: calc'd 444 (MH+), measured 444 (MH+). 1 H NMR (400MHz, METHANOL-d4) d = 9.01 (dd, 7=1.6, 4.3 Hz, 1H), 8.68 (dd, 7=1.7, 8.6 Hz, 1H), 8.18 (d, 7=7.9 Hz, 1H), 7.67 (dd, 7=4.3, 8.6 Hz, 1H), 7.64 (d, 7=7.5 Hz, 1H), 7.30 (d, 7=7.9 Hz, 1H), 6.66 (dd, 7=2.6, 7.6 Hz, 1H), 6.17 (d, 7=2.4 Hz, 1H), 4.58 - 4.48 (m, 1H), 4.27 - 4.15 (m, 1H), 4.09 - 3.75 (m, 4H), 3.68 - 3.49 (m, 4H), 3.48 - 3.39 (m, 4H), 2.84 - 2.71 (m, 2H), 1.33 (d, 7=6.2 Hz, 3H).
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