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[ CAS No. 1232038-69-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1232038-69-5
Chemical Structure| 1232038-69-5
Chemical Structure| 1232038-69-5
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Product Details of [ 1232038-69-5 ]

CAS No. :1232038-69-5 MDL No. :MFCD22627990
Formula : C7H4BrIN2 Boiling Point : -
Linear Structure Formula :- InChI Key :FPBVVGOLLSNULG-UHFFFAOYSA-N
M.W : 322.93 Pubchem ID :58449900
Synonyms :

Calculated chemistry of [ 1232038-69-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.61
TPSA : 17.3 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) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 3.14
Log Po/w (WLOGP) : 2.7
Log Po/w (MLOGP) : 2.35
Log Po/w (SILICOS-IT) : 2.59
Consensus Log Po/w : 2.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.43
Solubility : 0.0121 mg/ml ; 0.0000375 mol/l
Class : Moderately soluble
Log S (Ali) : -3.17
Solubility : 0.217 mg/ml ; 0.000672 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.87
Solubility : 0.0441 mg/ml ; 0.000136 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.28

Safety of [ 1232038-69-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1232038-69-5 ]

* 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 [ 1232038-69-5 ]

[ 1232038-69-5 ] Synthesis Path-Downstream   1~44

  • 1
  • [ 1232038-69-5 ]
  • [ 1765-93-1 ]
  • [ 1232038-71-9 ]
YieldReaction ConditionsOperation in experiment
19.4% With potassium phosphate In ethanol at 20℃; for 2h; A.3.b A mixture of intermediate 5 (0.577 g, 1.79 mmol), (4-fluorophenyl)boronic acid (275 mg, 1.97 mmol), DAPCy catalyst (52.28 mg, 0.089 mmol) and K3PO4 (1.14 g, 5.36 mmol) in EtOH (10 ml) was stirred at r.t. for 2 h. The solids were filtered off and the filtrate was evaporated in vacuo. The residue was taken up in DCM, washed with a sat. aq. NaHCO3 solution, dried (MgSO4), filtered and the solvent was evaporated in vacuo to yield a residue that was purified by flash chromatography over silicagel (eluent: DCM/MeOH (NH3) from 100/0 to 98/2). The product fractions were combined and the solvent was evaporated in vacuo. Yield: 0.101 g of intermediate 6 (19.4 %).
19% With potassium phosphate; trans-diacetylpalladium(II) bis(dicyclohexylamine) In ethanol for 2h;
  • 2
  • [ 850349-02-9 ]
  • [ 1232038-69-5 ]
YieldReaction ConditionsOperation in experiment
84.6% With N-iodo-succinimide; In acetonitrile; at 20℃; for 0.5h; l-Iodo-2,5-pyrrolidinedione (2.28 g, 10.15 mmol) was added to a solution of 8-bromo- imidazo[l,2-a]pyridine (2 g, 10.15 mmol) in CH3CN (8 ml). The r.m. was stirred at r.t. for 30 min. The mixture was concentrated in vacuo and the residue was purified by flash chromatography over silicagel (eluent: DCM/MeOH(NH3) from 100/0 to 99/1). The product fractions were collected and the solvent was evaporated in vacuo. Yield: 2.89 g of intermediate 5 (84.6 %).
  • 4
  • [ 1232038-69-5 ]
  • [ 121219-16-7 ]
  • 8-bromo-3-(2,3-difluorophenyl)imidazo[1,2-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 2h; Microwave irradiation; Sealed tube; 27 8-bromo-3-iodoimidazo[l,2-a]pyridine (100 mg, 0.31 mmole) was combinded with (2,3-difluorophenyl)boronic acid (49 mg, 0.31 mmole), [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.05 equiv), and potassium carbonate (42 mg, 0.31 mmol) in microwave seal tube. To this mixture was added dimethylformamide (2 mL) and water (0.2 mL). The resulting mixture was stirred at 90°C for 120 min. Reaction was cooled and diluted with EtOAc and filtered through celite. The filtrate was concentrated, and solid was precipitated out of DMF/H2O mixture to give 8-bromo-3-(2,3- difluorophenyl)imidazo[l,2-a]pyridine. 309.0 (M). The precipitate used as such for the next step.
  • 5
  • [ 1232038-69-5 ]
  • (x)C2HF3O2*C26H14F6N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 2 h / 90 °C / Microwave irradiation; Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 2 h / Inert atmosphere; Sealed tube; Reflux 3: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 0.33 h / 120 °C / Microwave irradiation
  • 6
  • [ 1232038-69-5 ]
  • 5-(3-(2,3-difluorophenyl)imidazo[1,2-a]pyridin-8-yl)-N-(4-fluorophenyl)-2-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 2 h / 90 °C / Microwave irradiation; Sealed tube 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 0.33 h / 120 °C / Microwave irradiation; Sealed tube
  • 7
  • [ 1232038-69-5 ]
  • 2-(5-(3-(2,3-difluorophenyl)imidazo[1,2-a]pyridin-8-yl)-2-(trifluoromethyl)phenyl)-5-fluoro-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 2 h / 90 °C / Microwave irradiation; Sealed tube 2: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 18 h / 100 °C / Microwave irradiation; Sealed tube
  • 8
  • [ 1232038-69-5 ]
  • (3-(2,3-difluorophenyl)imidazo[1,2-a]pyridin-8-yl)boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide; water / 2 h / 90 °C / Microwave irradiation; Sealed tube 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 2 h / Inert atmosphere; Sealed tube; Reflux
  • 9
  • [ 1232038-69-5 ]
  • [ 1765-93-1 ]
  • [ 1232035-15-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium phosphate; trans-diacetylpalladium(II) bis(dicyclohexylamine) / ethanol / 2 h 2: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 100 °C / Inert atmosphere
  • 10
  • [ 1006055-08-8 ]
  • [ 1232038-69-5 ]
  • 4,5-dibromo-N-(3-(8-bromoimidazo[1,2-a]pyridin-3-yl)prop-2-yn-1-yl)-1H-pyrrole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Inert atmosphere;
  • 11
  • [ 1232038-69-5 ]
  • N-(3-ethynylphenyl)-3-phenyl-3,4-dihydropyrazole-2-carboxamide [ No CAS ]
  • N-[3-[2-(8-bromoimidazo[1,2-a]pyridin-3-yl)ethynyl]phenyl]-3-phenyl-3,4-dihydropyrazole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.1 g With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In ethyl acetate; N,N-dimethyl-formamide at 70℃; for 6h; Inert atmosphere; 65.3 Step 3: Preparation of -N-[3-[2-(8-bromoimidazo[1,2-a]pyridin-3-yl)ethynyl]phenyl]-3-phenyl-3,4-dihydropyrazole-2-carboxamide The compound 8-bromo-3-iodo-imidazo[1,2-a]pyridine (800 mg, 2.48 mmol) obtained in step 2 above and the compound N-(3-ethynylphenyl)-3-phenyl-3,4-dihydropyrazole-2-carboxamide (788.45 mg, 2.73 mmol) obtained in step 1 of Example 1 were dissolved in DMF (10 mL), and the gas was removed by ultrasonic treatment for 5 minutes while blowing nitrogen. CuI (235.90 mg, 1.24 mmol), ethyl acetate (1.72 mL, 12.39 mmol) and Pd(PPh3)4 (858.81 mg, 743.20 umol) were added thereto, followed by reaction at 70° C. for 6 hours. Upon completion of the reaction, the temperature was lowered to room temperature, and H2O (10 mL) and ethyl acetate (50 mL) were added to the reaction mixture, followed by extraction with ethyl acetate and brine, and the organic layers were combined. The organic layer was dried over sodium sulfate, concentrated under reduced pressure, and purified by medium pressure liquid chromatography (petronium ether/ethyl acetate) to give the target compound N-[3-[2-(8-bromoimidazo[1,2-a]pyridin-3-ethynyl]phenyl]-3-phenyl-3,4-dihydropyrazole-2-carboxamide (1.1 g, 91.7%) as a yellow solid. MS: m/z 486.1 [M+H]+ 1H NMR (400 MHz, DMSO-d6) δ 9.25 (s, 1H), 8.61 (d, J=6.6 Hz, 1H), 8.07 (s, 1H), 8.01-7.94 (m, 1H), 7.78 (d, J=7.3 Hz, 1H), 7.67-7.59 (m, 2H), 7.38-7.33 (m, 2H), 7.29-7.17 (m, 5H), 7.05 (t, J=7.0 Hz, 1H), 5.33 (m, 1H), 3.57 (m, 1H), 2.82-2.72 (m, 1H)
  • 12
  • [ 1232038-69-5 ]
  • 3-[(4-methoxyphenyl)methyl]hexahydropyrimidine-2,4-dione [ No CAS ]
  • 1-(8-bromoimidazo[1,2-a]pyridin-3-yl)-3-(4-methoxybenzyl)dihydropyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine; Cs2CO3 In 1,4-dioxane at 60℃; for 6h; Inert atmosphere; 2 Step 2 - 1-(8-Bromoimidazo[1,2-a]pyridin-3-yl)-3-(4-methoxybenzyl)dihydropyrimidine-2,4(1H,3H) dione A mixture of 8-bromo-3-iodo-imidazo[l,2-a]pyridine (500 mg, 1.55 mmol) and 3-(4-methoxybenzyl) dihydropyrimidine-2,4(1H,3H)-dione (362 mg, 1.55 mmol, Intermediate GK), Cul (58.9 mg, 309 umol), Cs2CO3 (1.01 g, 3.10 mmol), and (1S,2S)-N1,N2-dimethylcyclohexane-1,2-diamine (44.0 mg, 309 umol) in dioxane (10 mL) was stirred at 60 °C for 6 hours under N2. On completion, the mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by reversed phase flash (120 g Flash Column, Welch Ultimate XB°C18, 20-40μm; 120 A, 5% to 35% MeCN in H2O, 0.5% FA in H2O) and then further purified by prep-HPLC (column: Waters xbridge, 150mm*25mm* 10um; mobile phase: [water(10 mM NH4HCO3)-MeCN]; B%: 22%-52%, 10min) to give the title compound (200 mg, 10% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.35 (dd, J= 0.8, 6.8 Hz, 1H), 7.69 -7.67 (m, 1H), 7.67 (s, 1H), 7.24 (d, J= 7.6 Hz, 2H), 6.91 (t, J = 7.2 Hz, 1H), 6.87 - 6.84 (m, 2H), 4.81 (s, 2H), 3.84 (t, J= 6.4 Hz, 2H), 3.72 (s, 3H), 3.02 (s, 2H).
10% With copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine; Cs2CO3 In 1,4-dioxane at 60℃; for 6h; Inert atmosphere; 2 Step 2 - 1-(8-Bromoimidazo[1,2-a]pyridin-3-yl)-3-(4-methoxybenzyl)dihydropyrimidine-2,4(1H,3H) dione A mixture of 8-bromo-3-iodo-imidazo[l,2-a]pyridine (500 mg, 1.55 mmol) and 3-(4-methoxybenzyl) dihydropyrimidine-2,4(1H,3H)-dione (362 mg, 1.55 mmol, Intermediate GK), Cul (58.9 mg, 309 umol), Cs2CO3 (1.01 g, 3.10 mmol), and (1S,2S)-N1,N2-dimethylcyclohexane-1,2-diamine (44.0 mg, 309 umol) in dioxane (10 mL) was stirred at 60 °C for 6 hours under N2. On completion, the mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by reversed phase flash (120 g Flash Column, Welch Ultimate XB°C18, 20-40μm; 120 A, 5% to 35% MeCN in H2O, 0.5% FA in H2O) and then further purified by prep-HPLC (column: Waters xbridge, 150mm*25mm* 10um; mobile phase: [water(10 mM NH4HCO3)-MeCN]; B%: 22%-52%, 10min) to give the title compound (200 mg, 10% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.35 (dd, J= 0.8, 6.8 Hz, 1H), 7.69 -7.67 (m, 1H), 7.67 (s, 1H), 7.24 (d, J= 7.6 Hz, 2H), 6.91 (t, J = 7.2 Hz, 1H), 6.87 - 6.84 (m, 2H), 4.81 (s, 2H), 3.84 (t, J= 6.4 Hz, 2H), 3.72 (s, 3H), 3.02 (s, 2H).
10% With copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine; Cs2CO3 In 1,4-dioxane at 60℃; for 6h; Inert atmosphere; 2 Step 2 - 1-(8-Bromoimidazo[1,2-a]pyridin-3-yl)-3-(4-methoxybenzyl)dihydropyrimidine- 2,4(1H,3H)-dione A mixture of 8-bromo-3-iodo-imidazo[1,2-a]pyridine (500 mg, 1.55 mmol), 3-(4- methoxybenzyl)dihydropyrimidine-2,4(1H,3H)-dione (362 mg, 1.55 mmol, Intermediate BRW), CuI (58.9 mg, 309 µmol), Cs2CO3(1.01 g, 3.10 mmol), and (1S,2S)-N1,N2-dimethylcyclohexane-1,2-diamine (44.0 mg, 309 µmol) in dioxane (10 mL) was stirred at 60 °C for 6 hours under N2. On completion, the mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by reversed phase flash (120 g Flash Column, Welch Ultimate XB_C18, 20-40μm; 120 A, 5% to 35% MeCN in H2O, 0.5% FA in H2O) and then further purified by prep-HPLC (column: Waters xbridge, 150mm*25mm*10um; mobile phase: [water(10 mM NH4HCO3)-MeCN]; B%: 22%-52%, 10min) to give the title compound (200 mg, 10% yield) as a yellow solid.1H NMR (400 MHz, DMSO-d6) δ 8.35 (dd, J = 0.8, 6.8 Hz, 1H), 7.69 - 7.67 (m, 1H), 7.67 (s, 1H), 7.24 (d, J = 7.6 Hz, 2H), 6.91 (t, J = 7.2 Hz, 1H), 6.87 - 6.84 (m, 2H), 4.81 (s, 2H), 3.84 (t, J = 6.4 Hz, 2H), 3.72 (s, 3H), 3.02 (s, 2H).
10% With copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine; Cs2CO3 In 1,4-dioxane at 60℃; for 6h; Inert atmosphere; 2 Step 2 - 1-(8-Bromoimidazo[1,2-a]pyridin-3-yl)-3-(4-methoxybenzyl)dihydropyrimidine- 2,4(1H,3H)-dione A mixture of 8-bromo-3-iodo-imidazo[1,2-a]pyridine (500 mg, 1.55 mmol), 3-(4- methoxybenzyl)dihydropyrimidine-2,4(1H,3H)-dione (362 mg, 1.55 mmol, Intermediate BRW), CuI (58.9 mg, 309 µmol), Cs2CO3(1.01 g, 3.10 mmol), and (1S,2S)-N1,N2-dimethylcyclohexane-1,2-diamine (44.0 mg, 309 µmol) in dioxane (10 mL) was stirred at 60 °C for 6 hours under N2. On completion, the mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by reversed phase flash (120 g Flash Column, Welch Ultimate XB_C18, 20-40μm; 120 A, 5% to 35% MeCN in H2O, 0.5% FA in H2O) and then further purified by prep-HPLC (column: Waters xbridge, 150mm*25mm*10um; mobile phase: [water(10 mM NH4HCO3)-MeCN]; B%: 22%-52%, 10min) to give the title compound (200 mg, 10% yield) as a yellow solid.1H NMR (400 MHz, DMSO-d6) δ 8.35 (dd, J = 0.8, 6.8 Hz, 1H), 7.69 - 7.67 (m, 1H), 7.67 (s, 1H), 7.24 (d, J = 7.6 Hz, 2H), 6.91 (t, J = 7.2 Hz, 1H), 6.87 - 6.84 (m, 2H), 4.81 (s, 2H), 3.84 (t, J = 6.4 Hz, 2H), 3.72 (s, 3H), 3.02 (s, 2H).

  • 13
  • [ 1232038-69-5 ]
  • 1-(8-bromoimidazo[1,2-a]pyridin-3-yl)dihydropyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine; copper (I) iodide; Cs2CO3 / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 2.5 h / 70 °C
Multi-step reaction with 2 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluorormethanesulfonic acid; trifluoroacetic acid / 2.5 h / 70 °C
  • 14
  • [ 1232038-69-5 ]
  • tert-butyl 4-[2-[3-(2,4-dioxohexahydropyrimidin-1-yl)imidazo[1,2-a]pyridin-8-yl]ethynyl]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide; caesium carbonate / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 2.5 h / 70 °C 3: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere
  • 15
  • [ 1232038-69-5 ]
  • 1-[8-[2-(4-piperidyl)ethynyl]imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide; caesium carbonate / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 2.5 h / 70 °C 3: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 4: dichloromethane / 0.5 h / 0 - 25 °C
  • 16
  • [ 1232038-69-5 ]
  • tert-butyl N-[4-[[4-[2-[3-(2,4-dioxohexahydropyrimidin-1-yl)imidazo[1,2-a]pyridin-8-yl]ethynyl]-1-piperidyl]methyl]cyclohexyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide; caesium carbonate / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 2.5 h / 70 °C 3.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 4.1: dichloromethane / 0.5 h / 0 - 25 °C 5.1: potassium acetate / tetrahydrofuran; N,N-dimethyl-formamide / 0.25 h / 25 °C 5.2: 14 h / 25 °C
  • 17
  • [ 1232038-69-5 ]
  • 1-[8-[2-[1-[(4-aminocyclohexyl)methyl]-4-piperidyl]ethynyl]imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide; caesium carbonate / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2.1: trifluoroacetic acid; trifluorormethanesulfonic acid / 2.5 h / 70 °C 3.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere 4.1: dichloromethane / 0.5 h / 0 - 25 °C 5.1: potassium acetate / tetrahydrofuran; N,N-dimethyl-formamide / 0.25 h / 25 °C 5.2: 14 h / 25 °C 6.1: dichloromethane / 1 h / 0 - 25 °C
  • 18
  • [ 1232038-69-5 ]
  • tert-butyl 4-[4-[3-(2,4-dioxohexahydropyrimidin-1-yl)imidazo[1,2-a]pyridin-8-yl]but-3-ynyl]piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide; caesium carbonate / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 2.5 h / 70 °C 3: methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); caesium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C / Molecular sieve
  • 19
  • [ 1232038-69-5 ]
  • 1-[8-(4-piperazin-1-ylbut-1-ynyl)imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide; caesium carbonate / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 2.5 h / 70 °C 3: methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); caesium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C / Molecular sieve 4: dichloromethane / 0.5 h / 25 °C
  • 20
  • [ 1232038-69-5 ]
  • 1-[8-(5-hydroxypent-1-ynyl)imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide; caesium carbonate / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 2.5 h / 70 °C 3: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 5 h / 100 °C / Inert atmosphere
  • 21
  • [ 1232038-69-5 ]
  • 5-[3-(2,4-dioxohexahydropyrimidin-1-yl)imidazo[1,2-a]pyridin-8-yl]pent-4-ynal [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide; caesium carbonate / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 2.5 h / 70 °C 3: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 5 h / 100 °C / Inert atmosphere 4: Dess-Martin periodane / dichloromethane / 2 h / 25 °C / Inert atmosphere
  • 22
  • [ 1232038-69-5 ]
  • tert-butyl 4-[3-[3-(2,4-dioxohexahydropyrimidin-1-yl)imidazo[1,2-a]pyridin-8-yl]prop-2-ynyl]piperazine-1-carboxylate formic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide; caesium carbonate / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 2.5 h / 70 °C 3: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere
  • 23
  • [ 1232038-69-5 ]
  • 1-[8-(3-piperazin-1-ylprop-1-ynyl)imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; copper(l) iodide; caesium carbonate / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 2.5 h / 70 °C 3: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere 4: dichloromethane / 0.5 h / 25 °C
  • 24
  • [ 1232038-69-5 ]
  • 1-[8-[4-(methylamino)-1-piperidyl]imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: Cs2CO3 / 1,4-dioxane / 12 h / 100 °C / Molecular sieve 3: trifluorormethanesulfonic acid; trifluoroacetic acid / 3 h / 60 °C
  • 25
  • [ 1232038-69-5 ]
  • tert-butyl (1-(3-(3-(4-methoxybenzyl)-2,4-dioxotetrahydropyrimidin-1(2H)-yl)imidazo[1,2-a]pyridin-8-yl)piperidin-4-yl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: Cs2CO3 / 1,4-dioxane / 12 h / 100 °C / Molecular sieve
  • 26
  • [ 1232038-69-5 ]
  • 1-[8-(4-piperidyl)imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione trifluoroacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluorormethanesulfonic acid; trifluoroacetic acid / 2.5 h / 70 °C 3: 2,6-dimethylpyridine / ethylene glycol dimethyl ether / 16 h / 25 °C / UV-irradiation 4: dichloromethane / 1 h / 25 °C
  • 27
  • [ 1232038-69-5 ]
  • tert-butyl 4-[3-(2,4-dioxohexahydropyrimidin-1-yl)imidazo[1,2-a]pyridin-8-yl]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluorormethanesulfonic acid; trifluoroacetic acid / 2.5 h / 70 °C 3: 2,6-dimethylpyridine / ethylene glycol dimethyl ether / 16 h / 25 °C / UV-irradiation
  • 28
  • [ 1232038-69-5 ]
  • 1-[8-[1-[[4-(5-aminoindazol-2-yl)cyclohexyl]methyl]-4-piperidyl]imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2.1: trifluorormethanesulfonic acid; trifluoroacetic acid / 2.5 h / 70 °C 3.1: 2,6-dimethylpyridine / ethylene glycol dimethyl ether / 16 h / 25 °C / UV-irradiation 4.1: dichloromethane / 1 h / 25 °C 5.1: triethylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 5.2: 0.33 h / -10 °C 5.3: 1 h / -10 °C 6.1: hydrogenchloride / 1,4-dioxane / 1 h / 25 °C
  • 29
  • [ 1232038-69-5 ]
  • tert-butyl N-[2-[4-[[4-[3-(2,4-dioxohexahydropyrimidin-1-yl)imidazo[1,2-a]pyridin-8-yl]-1-piperidyl]methyl]cyclohexyl]indazol-5-yl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2.1: trifluorormethanesulfonic acid; trifluoroacetic acid / 2.5 h / 70 °C 3.1: 2,6-dimethylpyridine / ethylene glycol dimethyl ether / 16 h / 25 °C / UV-irradiation 4.1: dichloromethane / 1 h / 25 °C 5.1: triethylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 5.2: 0.33 h / -10 °C 5.3: 1 h / -10 °C
  • 30
  • [ 1232038-69-5 ]
  • 1-[8-[3-[[(3S,4S)-3-methyl-4-piperidyl]oxy]prop-1-ynyl]imidazo[1,2-a]pyridin-3-yl] hexahydropyrimidine-2,4-dione trifluoroacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluorormethanesulfonic acid; trifluoroacetic acid / 2.5 h / 70 °C 3: Cs2CO3; copper (I) iodide; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere 4: dichloromethane / 2 h / 25 °C
  • 31
  • [ 1232038-69-5 ]
  • 1-[8-[3-[[(3S,4S)-3-methyl-4-piperidyl]oxy]prop-1-ynyl]imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluorormethanesulfonic acid; trifluoroacetic acid / 2.5 h / 70 °C 3: Cs2CO3; copper (I) iodide; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere
  • 32
  • [ 1232038-69-5 ]
  • 1-[8-(3,6-diazabicyclo[3.1.1]heptan-3-yl)imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: Cs2CO3 / 1,4-dioxane / 16 h / 100 °C / Molecular sieve; Inert atmosphere 3: trifluorormethanesulfonic acid; trifluoroacetic acid / 12 h / 70 °C
  • 33
  • [ 1232038-69-5 ]
  • tert-butyl 3-[3-[3-[(4-methoxyphenyl)methyl]-2,4-dioxohexahydropyrimidin-1-yl]imidazo[1,2-a]pyridin-8-yl]-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: Cs2CO3 / 1,4-dioxane / 16 h / 100 °C / Molecular sieve; Inert atmosphere
  • 34
  • [ 1232038-69-5 ]
  • 1-[8-[(1R,4R)-2,5-diazabicyclo[2.2.1]heptan-2-yl]imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione trifluoroacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: Cs2CO3 / 1,4-dioxane / 12 h / 100 °C / Molecular sieve; Inert atmosphere 3: trifluorormethanesulfonic acid / 1 h / 70 °C
Multi-step reaction with 3 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: Cs2CO3 / 1,4-dioxane / 16 h / 100 °C / Molecular sieve; Inert atmosphere 3: trifluorormethanesulfonic acid / 1 h / 70 °C
  • 35
  • [ 1232038-69-5 ]
  • tert-butyl (1R,4R)-5-[3-[3-[(4-methoxyphenyl)methyl]-2,4-dioxohexahydropyrimidin-1-yl]imidazo[1,2-a]pyridin-8-yl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: Cs2CO3 / 1,4-dioxane / 12 h / 100 °C / Molecular sieve; Inert atmosphere
  • 36
  • [ 1232038-69-5 ]
  • tert-butyl (1S,4S)-5-[3-[3-[(4-methoxyphenyl)methyl]-2,4-dioxohexahydropyrimidin-1-yl]imidazo[1,2-a]pyridin-8-yl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: Cs2CO3 / 1,4-dioxane / 16 h / 100 °C / Molecular sieve; Inert atmosphere
  • 37
  • [ 1232038-69-5 ]
  • 1-[8-(3,8-diazabicyclo[3.2.1]octan-3-yl)imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione trifluoroacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: Cs2CO3 / 1,4-dioxane / 16 h / 100 °C / Molecular sieve; Inert atmosphere 3: trifluorormethanesulfonic acid / 3 h / 70 °C
  • 38
  • [ 1232038-69-5 ]
  • tert-butyl 3-[3-[3-[(4-methoxyphenyl)methyl]-2,4-dioxohexahydropyrimidin-1-yl]imidazo[1,2-a]pyridin-8-yl]-3,8-diazabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: Cs2CO3 / 1,4-dioxane / 16 h / 110 °C / Molecular sieve; Inert atmosphere
  • 39
  • [ 1232038-69-5 ]
  • 1-[8-[3-[[(3R,4R)-3-methyl-4-piperidyl]oxy]prop-1-ynyl]imidazo[1,2-a]pyridin-3-yl]hexahydropyrimidine-2,4-dione trifluoroacetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluorormethanesulfonic acid; trifluoroacetic acid / 2.5 h / 70 °C 3: Cs2CO3; copper (I) iodide; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere 4: dichloromethane / 1 h / 25 °C
  • 40
  • [ 1232038-69-5 ]
  • tert-butyl (3R,4R)-4-[3-[3-(2,4-dioxohexahydropyrimidin-1-yl)imidazo[1,2-a]pyridin-8-yl]prop-2-ynoxy]-3-methylpiperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluorormethanesulfonic acid; trifluoroacetic acid / 2.5 h / 70 °C 3: Cs2CO3; copper (I) iodide; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere
  • 41
  • [ 1232038-69-5 ]
  • tert-butyl 4-(3-(3-(4-methoxybenzyl)-2,4-dioxotetrahydropyrimidin-1(2H)-yl)imidazo[1,2-a]pyridin-8-yl)-5,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: tripotassium phosphate tribasic / 1,4-dioxane; lithium hydroxide monohydrate / 5 h / 80 °C
  • 42
  • [ 1232038-69-5 ]
  • tert-butyl 4-((3-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)imidazo[1,2-a]pyridin-8-yl)prop-2-yn-1-yl)oxy)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: trifluorormethanesulfonic acid; trifluoroacetic acid / 2.5 h / 70 °C 3: Cs2CO3; copper (I) iodide; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere
  • 43
  • [ 1232038-69-5 ]
  • tert-butyl 4-[3-[3-[(4-methoxyphenyl)methyl]-2,4-dioxohexahydropyrimidin-1-yl]imidazo[1,2-a]pyridin-8-yl]-1,4-diazepane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2: Cs2CO3 / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere
  • 44
  • [ 1232038-69-5 ]
  • C35H34F3N9O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: Cs2CO3; copper (I) iodide; (1S,2S )-N,N’-dimethyl-1,2-cyclohexanediamine / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere 2.1: trifluorormethanesulfonic acid; trifluoroacetic acid / 2.5 h / 70 °C 3.1: 2,6-dimethylpyridine / ethylene glycol dimethyl ether / 16 h / 25 °C / UV-irradiation 4.1: dichloromethane / 1 h / 25 °C 5.1: triethylamine / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -10 °C 5.2: 5.5 h / -20 - -10 °C
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