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[ CAS No. 2486-74-0 ] {[proInfo.proName]}

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Chemical Structure| 2486-74-0
Chemical Structure| 2486-74-0
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Product Details of [ 2486-74-0 ]

CAS No. :2486-74-0 MDL No. :MFCD18409912
Formula : C9H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WDTLFYSTDFWPOF-UHFFFAOYSA-N
M.W : 165.19 Pubchem ID :17921342
Synonyms :

Calculated chemistry of [ 2486-74-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 47.58
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) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.21
Log Po/w (XLOGP3) : 1.57
Log Po/w (WLOGP) : 1.54
Log Po/w (MLOGP) : 0.53
Log Po/w (SILICOS-IT) : 1.29
Consensus Log Po/w : 1.23

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.09
Solubility : 1.34 mg/ml ; 0.0081 mol/l
Class : Soluble
Log S (Ali) : -2.51
Solubility : 0.51 mg/ml ; 0.00309 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.19
Solubility : 1.05 mg/ml ; 0.00638 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.17

Safety of [ 2486-74-0 ]

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 [ 2486-74-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2486-74-0 ]

[ 2486-74-0 ] Synthesis Path-Downstream   1~39

  • 1
  • [ 90564-18-4 ]
  • [ 2486-74-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; tin
  • 2
  • [ 577-56-0 ]
  • [ 2486-74-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: alkali; sodium amalgam / Behandeln mit Salzsaeure 2: hydriodic acid; yellow phosphorus / 137 °C 3: concentrated nitric acid / Behandeln mit konz. Schwefelsaeure mit Trennung des Gemisches durch fraktionierte Krystallisation aus Wasser, Chloroform oder Benzol 4: tin; hydrochloric acid
  • 3
  • [ 3453-64-3 ]
  • [ 2486-74-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydriodic acid; yellow phosphorus / 137 °C 2: concentrated nitric acid / Behandeln mit konz. Schwefelsaeure mit Trennung des Gemisches durch fraktionierte Krystallisation aus Wasser, Chloroform oder Benzol 3: tin; hydrochloric acid
  • 4
  • [ 612-19-1 ]
  • [ 2486-74-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: concentrated nitric acid / Behandeln mit konz. Schwefelsaeure mit Trennung des Gemisches durch fraktionierte Krystallisation aus Wasser, Chloroform oder Benzol 2: tin; hydrochloric acid
  • 5
  • [ 1211589-24-0 ]
  • [ 2486-74-0 ]
YieldReaction ConditionsOperation in experiment
60.5% With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 15h; Inert atmosphere; 3 Step 3: 4-amino-2-ethyl-benzoic acid To a solution of methyl 4-amino-2-ethylbenzoate (540 mg, 3.0 mmol) in THF (5 mL) and methanol (25 mL) was added 2.0 M LiOH (3.0 mL) aqueous solution. The resultant mixture was stirred for 15 h at room temperature and then acidified to pH=5-6 with 3.0 M hydrochloric acid. The resulting suspension was filtered, the solid was washed with water and then dried to give the title compound (0.3 g, 60.5% yield) as a white solid MS (ESI, m/z): 166.0 [M+H]+.
60.5% With methanol; water; lithium hydroxide In tetrahydrofuran at 20℃; for 15h; Inert atmosphere; 3 Step 3: 4-amino-2-ethyl-benzoic acid To a solution of methyl 4-amino-2-ethylbenzoate (540 mg, 3.0 mmol) in THF (5 mL) and methanol (25 mL) was added 2.0 M LiOH (3.0 mL) aqueous solution. The resultant mixture was stirred for 15 h at room temperature and then acidified to pH=5-6 with 3.0 M hydrochloric acid. The resulting suspension was filtered, the solid was washed with water and then dried to give the title compound (0.3 g, 60.5% yield) as a white solidMS (ESI, m/z): 166.0 [M+H]+.
60.5% With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 15h; 3 Step 3: 4-amino-2-ethyl-benzoic acid To a solution of methyl 4-amino-2-ethylbenzoate (540 mg, 3.0 mmol) in THF (5 mL) and methanol (25 mL) was added 2.0 M LiOH (3.0 mL) aqueous solution. The resultant mixture was stirred for 15 h at room temperature and then acidified to pH=5-6 with 3.0 M hydrochloric acid. The resulting suspension was filtered, the solid was washed with water and then dried to give the title compound (0.3 g, 60.5% yield) as a white solid (0757) MS (ESI, m/z): 166.0 [M+H]+.
60.5% With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 15h; 3 Step 3: 4-amino-2-ethyl-benzoic acid To a solution of methyl 4-amino-2-ethylbenzoate (540 mg, 3.0 mmol) in THF (5 mL) and methanol (25 mL) was added 2.0 M LiOH (3.0 mL) aqueous solution. The resultant mixture was stirred for 15 h at room temperature and then acidified to pH=5-6 with 3.0 M hydrochloric acid. The resulting suspension was filtered, the solid was washed with water and then dried to give the title compound (0.3 g, 60.5% yield) as a white solid MS (ESI, m/z): 166.0 [M+H]+.

  • 6
  • [ 2486-74-0 ]
  • 8-chloro-3-(2,3-difluoro-4-methoxy-phenyl)imidazo[1,2-a]pyrazine [ No CAS ]
  • 4-[[3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethylbenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.64% With acetic acid In acetonitrile at 65℃; for 12h; Inert atmosphere; 479.2 Step 2: 4-((3-(2,3-difluoro-4-methoxyphenyl)imidazo[l,2-a]pyrazin-8-yl)amino)-2- ethylbenzoic acid A mixture of 4-amino-2-ethyl-benzoic acid (216.91 mg, 1.12 mmol, 1.1 eq) and 8-chloro-3-(2,3- difluoro-4-methoxy-phenyl)imidazo[l,2-a]pyrazine (300.0 mg, 1.01 mmol, 1 eq) in acetonitrile (6.3 mL) and acetic acid (0.700 mL) was stirred for 12 h at 65 °C. The solvent was removed in vacuo to give 4-[[3-(2,3-difluoro-4-methoxy-phenyl)imidazo[l,2-a]pyrazin-8-yl]amino]-2-ethyl- benzoic acid (400 mg, 0.940 mmol, 72.64 % yield) as an off-white solid, which was used without further purification in the next step. MS (ESI) m/z: 425.0 [M+H]+
72.64% With acetic acid In acetonitrile at 65℃; for 12h; Inert atmosphere; 158.2 Step 2: 4-((3-(2,3-difhioro-4-methoxyphenyl)imidazo[l,2-a]pyrazin-8-yl)amino)-2-ethylbenzoic acid A mixture of 4-amino-2-ethyl-benzoic acid (216.91 mg, 1.12 mmol, 1.1 eq) and 8-chloro-3-(2,3- difluoro-4-methoxy-phenyl)imidazo[l,2-a]pyrazine (300.0 mg, 1.01 mmol, 1 eq) in acetonitrile (6.3 mL) and acetic acid (0.700 mL) was stirred for 12 h at 65 °C. The solvent was removed in vacuo to give 4-[[3-(2,3-difluoro-4-methoxy-phenyl)imidazo[l,2-a]pyrazin-8-yl]amino]-2-ethyl- benzoic acid (400 mg, 0.940 mmol, 72.64 % yield) as an off-white solid, which was used without further purification in the next step. MS (ESI) m/z: 425.0 [M+H]+
72.64% With acetic acid In acetonitrile at 65℃; for 12h; 463.2 Step 2: 4-((3-(2,3-difluoro-4-methoxyphenyl)imidazo[l,2-a]pyrazin-8-yl)amino)-2- ethylbenzoic acid A mixture of 4-amino-2-ethyl-benzoic acid (216.91 mg, 1.12 mmol, 1.1 eq) and 8-chloro-3-(2,3- difluoro-4-methoxy-phenyl)imidazo[l,2-a]pyrazine (300.0 mg, 1.01 mmol, 1 eq) in acetonitrile (6.3 mL) and acetic acid (0.700 mL) was stirred for 12 h at 65 °C. The solvent was removed in vacuo to give 4-[[3-(2,3-difluoro-4-methoxy-phenyl)imidazo[l,2-a]pyrazin-8-yl]amino]-2-ethyl- benzoic acid (400 mg, 0.940 mmol, 72.64 % yield) as an off-white solid, which was used without further purification in the next step. MS (ESI) m/z: 425.0 [M+H]+
With acetic acid In acetonitrile at 65℃; for 12h; 515.2 Step 2: 4-((3-(2,3-difluoro-4-methoxyphenyl)imidazo[l,2-a]pyrazin-8-yl)amino)-2- ethylbenzoic acid A mixture of 4-amino-2-ethyl-benzoic acid (216.91 mg, 1.12 mmol, 1.1 eq) and 8-chloro-3-(2,3- difluoro-4-methoxy-phenyl)imidazo[l,2-a]pyrazine (300.0 mg, 1.01 mmol, 1 eq) in acetonitrile (6.3 mL) and acetic acid (0.700 mL) was stirred for 12 h at 65 °C. The solvent was removed in vacuo to give 4-[[3-(2,3-difluoro-4-methoxy-phenyl)imidazo[l,2-a]pyrazin-8-yl]amino]-2-ethyl- benzoic acid (400 mg, 0.940 mmol, 72.64 % yield) as an off-white solid, which was used without further purification in the next step. MS (ESI) m/z: 425.0 [M+H]+

  • 7
  • [ 2486-74-0 ]
  • cis-tert-butyl N-[3-[[4-[[3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethyl-benzoyl]amino]cyclobutyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid / acetonitrile / 12 h / 65 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
  • 8
  • [ 2486-74-0 ]
  • cis N-(3-aminocyclobutyl)-4-[[3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid / acetonitrile / 12 h / 65 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C / Inert atmosphere
  • 9
  • [ 2486-74-0 ]
  • (2,5-dioxopyrrolidin-1-yl) 4-[[3-(2,3-difluoro-4-methoxy-phenyl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethyl-benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid / acetonitrile / 12 h / 65 °C / Inert atmosphere 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 25 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: acetic acid / acetonitrile / 12 h / 65 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 25 °C
Multi-step reaction with 2 steps 1: acetic acid / acetonitrile / 12 h / 65 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 25 °C
  • 10
  • [ 2486-74-0 ]
  • N-[2-(2-aminoethoxy)ethyl]-4-[[3-(2,3-difluoro-4-methoxy-phenyl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid / acetonitrile / 12 h / 65 °C / Inert atmosphere 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 25 °C / Inert atmosphere 3: triethylamine / tetrahydrofuran / 3 h / 25 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: acetic acid / acetonitrile / 12 h / 65 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 25 °C 3: triethylamine / tetrahydrofuran / 3 h / 25 °C
Multi-step reaction with 3 steps 1: acetic acid / acetonitrile / 12 h / 65 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 25 °C 3: triethylamine / tetrahydrofuran / 3 h / 25 °C
  • 11
  • [ 2486-74-0 ]
  • methyl 2-[2-[2-[[4-[[3-(2,3-difluoro-4-methoxy-phenyl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethyl-benzoyl]amino]ethoxy]ethylamino]acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic acid / acetonitrile / 12 h / 65 °C / Inert atmosphere 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 25 °C / Inert atmosphere 3: triethylamine / tetrahydrofuran / 3 h / 25 °C / Inert atmosphere 4: triethylamine / N,N-dimethyl-formamide / 4 h / 25 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: acetic acid / acetonitrile / 12 h / 65 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 25 °C 3: triethylamine / tetrahydrofuran / 3 h / 25 °C 4: triethylamine / N,N-dimethyl-formamide / 4 h / 25 °C
Multi-step reaction with 4 steps 1: acetic acid / acetonitrile / 12 h / 65 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 25 °C 3: triethylamine / tetrahydrofuran / 3 h / 25 °C 4: triethylamine / N,N-dimethyl-formamide / 4 h / 25 °C
  • 12
  • [ 2486-74-0 ]
  • 2-((2-(2-(4-((3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-yl)amino)-2-ethylbenzamido)ethoxy)ethyl)amino)acetic acid formic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: acetic acid / acetonitrile / 12 h / 65 °C / Inert atmosphere 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 25 °C / Inert atmosphere 3: triethylamine / tetrahydrofuran / 3 h / 25 °C / Inert atmosphere 4: triethylamine / N,N-dimethyl-formamide / 4 h / 25 °C / Inert atmosphere 5: water; sodium hydroxide / methanol / 4 h / 25 °C / Inert atmosphere
  • 13
  • [ 2486-74-0 ]
  • tert-butyl 2-(4-((3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-yl)amino)-2-ethylbenzamido)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetic acid / acetonitrile / 12 h / 65 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.2 h / 10 °C / Inert atmosphere 2.2: 15 h / 10 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: acetic acid / acetonitrile / 12 h / 65 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.2 h / 10 °C / Inert atmosphere 2.2: 15 h / 10 °C
Multi-step reaction with 2 steps 1.1: acetic acid / acetonitrile / 12 h / 65 °C 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.2 h / 10 °C 2.2: 15 h / 10 °C
Multi-step reaction with 2 steps 1.1: acetic acid / acetonitrile / 12 h / 65 °C 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.2 h / 10 °C 2.2: 15 h / 10 °C

  • 14
  • [ 2486-74-0 ]
  • 2-(4-((3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-yl)amino)-2-ethylbenzamido)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetic acid / acetonitrile / 12 h / 65 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.2 h / 10 °C / Inert atmosphere 2.2: 15 h / 10 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane / 15 h / 30 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: acetic acid / acetonitrile / 12 h / 65 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.2 h / 10 °C / Inert atmosphere 2.2: 15 h / 10 °C 3.1: hydrogenchloride / 1,4-dioxane; water / 15 h / 30 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: acetic acid / acetonitrile / 12 h / 65 °C 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.2 h / 10 °C 2.2: 15 h / 10 °C 3.1: hydrogenchloride / 1,4-dioxane / 15 h / 30 °C
Multi-step reaction with 3 steps 1.1: acetic acid / acetonitrile / 12 h / 65 °C 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.2 h / 10 °C 2.2: 15 h / 10 °C 3.1: hydrogenchloride / 1,4-dioxane / 15 h / 30 °C

  • 15
  • [ 100959-22-6 ]
  • 2,4,6-trivinylcyclotriboroxane*pyridine complex [ No CAS ]
  • [ 2486-74-0 ]
YieldReaction ConditionsOperation in experiment
1.58 g With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 90℃; for 2h; Inert atmosphere; 1 Step 1: methyl 4-nitro-2- vinyl-benzoate & ethyl 4-nitro-2- vinyl-benzoate A mixture of methyl 2-bromo-4-nitro-benzoate (5.2 g, 20 mmol, 1 eq), 2, 4,6- trivinyl cyclotriboroxane pyridine complex (5.78 g, 24 mmol, 1.2 eq), (1236) tetrakis(triphenylphosphine)palladium(0) (1.16 g, 1 mmol, 0.050 eq) and potassium carbonate (11.05 g, 79.99 mmol, 4 eq) in toluene (50 mL) and ethanol (50 mL) was stirred at 90 °C under nitrogen for 2 h. The mixture was filtered over Celite. The filtrate was concentrated to dryness. To the crude was added water (50 mL). The mixture was extracted with ethyl acetate (50 mL c 3). The combined organic layers were concentrated to dryness. The crude was then purified by flash column chromatography eluting 10% ethyl acetate in petrol ether to afford methyl 4-nitro- 2-vinyl-benzoate (1.58 g) as a brown oil.
  • 16
  • [ 959778-16-6 ]
  • [ 2486-74-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen; palladium 10% on activated carbon / methanol / 5 h / 25 °C 2: lithium hydroxide; water / tetrahydrofuran / 15 h / 20 °C
  • 17
  • [ 1283128-54-0 ]
  • [ 2486-74-0 ]
YieldReaction ConditionsOperation in experiment
60.5% With water; lithium hydroxide In tetrahydrofuran at 20℃; for 15h; 3 Step 3: 4-amino-2-ethyl-benzoic acid To a solution of methyl 4-amino-2-ethylbenzoate (540 mg, 3.0 mmol) in THF (5 mL) and methanol (25 mL) was added 2.0 M LiOH (3.0 mL) aqueous solution. The resultant mixture was stirred for 15 h at room temperature and then acidified to pH=5-6 with 3.0 M hydrochloric acid. The resulting suspension was filtered, the solid was washed with water and then dried to give the title compound (0.3 g, 60.5% yield) as a white solid (1241) MS (ESI, m/z): 166.0 [M+H]+.
  • 18
  • [ 2486-74-0 ]
  • cis N-(3-aminocyclobutyl)-4-[[3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid / acetonitrile / 12 h / 65 °C / Inert atmosphere 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: acetic acid / acetonitrile / 12 h / 65 °C 2: HATU / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: acetic acid / acetonitrile / 12 h / 65 °C 2: HATU / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane; methanol / 3 h / 20 °C / Inert atmosphere
  • 19
  • [ 2486-74-0 ]
  • cis-tert-butyl N-[3-[[4-[[3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethylbenzoyl]amino]cyclobutyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid / acetonitrile / 12 h / 65 °C / Inert atmosphere 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: acetic acid / acetonitrile / 12 h / 65 °C 2: HATU / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: acetic acid / acetonitrile / 12 h / 65 °C 2: HATU / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
  • 20
  • [ 2486-74-0 ]
  • tert-butyl N-[2-(2-aminoethoxy)-1,1-dimethyl-ethyl]carbamate [ No CAS ]
  • tert-butyl N-[2-[2-[(4-amino-2-ethyl-benzoyl)amino]ethoxy]-1,1-dimethylethyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% Stage #1: 4-amino-2-ethyl-benzoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 10℃; for 0.5h; Stage #2: tert-butyl N-[2-(2-aminoethoxy)-1,1-dimethyl-ethyl]carbamate In N,N-dimethyl-formamide at 15℃; for 16h; 170.1 Step 1: tert-butyl N-[2-[2-[(4-amino-2-ethyl-benzoyl)amino]ethoxy]-l, 1-dimethyl- ethyl]carbamate A mixture of 4-amino-2-ethyl-benzoic acid (175.0 mg, 1.06 mmol, 1 eq), N,N- diisopropylethylamine (0.37 mL, 2.12 mmol, 2 eq), 0-(7-azabenzotriazol-l-yl)-N,N,N',N'- tetramethyluronium hexafluorophosphate (483.37 mg, 1.27 mmol, 1.2 eq) in DMF (7 mL) was stirred at 10 °C for 0.5 h, then tert-butyl N-[2-(2-aminoethoxy)-l,l-dimethyl-ethyl]carbamate (Intermediate 4, 270.73 mg, 1.17 mmol, 1.1 eq) was added. The mixture was stirred at 15 °C for 16 h. The mixture was diluted with water (30 mL) and extracted wirh EtOAc (30mL*2). The combined organic layers were washed with brine (20 mL*2), dried over sodium sulfate, filtered and concentrated in vacuum to give the crude product, wH-ich was purified by prep-HPLC to give the title compound (100 mg, 0.260 mmol, 25% yield) as a light yellow solid. MS (ESI, m/z): 402.2 [M+Na]+
  • 21
  • [ 2486-74-0 ]
  • 2-[2-[2-[[4-[[3-(2,3-difluoro-4-methoxyphenyl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethylbenzoyl]amino]ethoxy]ethylamino]acetic acid, formic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: acetic acid / acetonitrile / 12 h / 65 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 25 °C 3: triethylamine / tetrahydrofuran / 3 h / 25 °C 4: triethylamine / N,N-dimethyl-formamide / 4 h / 25 °C 5: water; sodium hydroxide / methanol / 4 h / 25 °C
  • 22
  • [ 1049677-32-8 ]
  • [ 2486-74-0 ]
  • 2-ethyl-4-[(3-iodoimidazo[1,2-a]pyrazin-8-yl)amino]benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With glacial acetic acid In acetonitrile at 100℃; for 48h; Inert atmosphere; Sealed tube; Microwave irradiation; 9.2; 3.1 2-Ethyl-4-((3-iodoimidazo[1,2-a]pyrazin-8-yl)amino)benzoic acid 4-Amino-2-ethylbenzoic acid (1500 mg, 9.08 mmol, Eq: 1) and 8-chloro-3-iodoimidazo[1,2- a]pyrazine (Intermediate 1, 2.66 g, 9.53 mmol, Eq: 1.05) was suspended in MeCN (16.5 ml) and AcOH (1.65 ml). The mixture was heated in a sealed microwave tube at 100 °C for 18h and then cooled to rt. The precipitate was collected by filtration and washed with ether (30 mL*3). The cake was dried in vacuo to afford the title compond (3.6 g off white solid, 97% yield) which was used in the next step without purification. MS (ESI, m/z): 409.0 [M+H]+
97% With glacial acetic acid In acetonitrile at 100℃; for 48h; Inert atmosphere; Sealed tube; Microwave irradiation; 9.2; 3.1 2-Ethyl-4-((3-iodoimidazo[1,2-a]pyrazin-8-yl)amino)benzoic acid 4-Amino-2-ethylbenzoic acid (1500 mg, 9.08 mmol, Eq: 1) and 8-chloro-3-iodoimidazo[1,2- a]pyrazine (Intermediate 1, 2.66 g, 9.53 mmol, Eq: 1.05) was suspended in MeCN (16.5 ml) and AcOH (1.65 ml). The mixture was heated in a sealed microwave tube at 100 °C for 18h and then cooled to rt. The precipitate was collected by filtration and washed with ether (30 mL*3). The cake was dried in vacuo to afford the title compond (3.6 g off white solid, 97% yield) which was used in the next step without purification. MS (ESI, m/z): 409.0 [M+H]+
95.5% With glacial acetic acid In acetonitrile at 100℃; for 18h; Sealed tube; 1 Step 1: 2-ethyl-4-[(3-iodoimidazo[1,2-a]pyrazin-8-yl)amino]benzoic acid 4-Amino-2-ethylbenzoic acid (3 g, 18.2 mmol) and 8-chloro-3-iodoimidazo[1,2-a]pyrazine (5.33 g, 19.1 mmol) was suspended in MeCN (33 mL) and AcOH (3.3 mL). The mixture heated in a sealed microwave tube at 100°C for 18 h, and then cooled to room temperature. The precipitate collected by filtration and washed with ether (30 mL X 3). The cake was dried in vacuum to afford the product 2-ethyl-4-((3-iodoimidazo[1,2-a]pyrazin-8-yl)amino)benzoic acid (7.08 g, 95.5% yield).
95.5% With glacial acetic acid In acetonitrile at 100℃; for 18h; Sealed tube; 1 Step 1: 2-ethyl-4-[(3-iodoimidazo[1,2-a]pyrazin-8-yl)amino]benzoic acid 4-Amino-2-ethylbenzoic acid (3 g, 18.2 mmol) and 8-chloro-3-iodoimidazo[1,2-a]pyrazine (5.33 g, 19.1 mmol) was suspended in MeCN (33 mL) and AcOH (3.3 mL). The mixture heated in a sealed microwave tube at 100°C for 18 h, and then cooled to room temperature. The precipitate collected by filtration and washed with ether (30 mL X 3). The cake was dried in vacuum to afford the product 2-ethyl-4-((3-iodoimidazo[1,2-a]pyrazin-8-yl)amino)benzoic acid (7.08 g, 95.5% yield).
95.5% With glacial acetic acid In acetonitrile at 100℃; for 18h; Sealed tube; Step 1: 2-ethyl-4-[(3-iodoimidazo[1,2-a]pyrazin-8-yl)amino]benzoic acid 4-Amino-2-ethylbenzoic acid (3 g, 18.2 mmol) and 8-chloro-3-iodoimidazo[1,2-a]pyrazine (5.33 g, 19.1 mmol) was suspended in MeCN (33 mL) and AcOH (3.3 mL). The mixture heated in a sealed microwave tube at 100°C for 18 h, and then cooled to room temperature. The precipitate collected by filtration and washed with ether (30 mL X 3). The cake was dried in vacuum to afford the product 2-ethyl-4-((3-iodoimidazo[1,2-a]pyrazin-8-yl)amino)benzoic acid (7.08 g, 95.5% yield).

  • 23
  • [ 2486-74-0 ]
  • 2-[4-(8-chloroimidazo[1,2-a]pyrazin-3-yl)-2,3-difluorophenoxy]acetonitrile [ No CAS ]
  • 4-[[3-[4-(cyanomethoxy)-2,3-difluorophenyl]imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethylbenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
69.24% With glacial acetic acid In acetonitrile at 100℃; for 3h; Inert atmosphere; 41.2 4-[[3-[4-(Cyanomethoxy)-2,3-difluoro-phenyl]imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethyl- benzoic acid A mixture of 2-[4-(8-chloroimidazo[1,2-a]pyrazin-3-yl)-2,3-difluoro-phenoxy]acetonitrile (573.0 mg, 1.79 mmol, 1 eq) and 4-amino-2-ethyl-benzoic acid (354.2 mg, 2.14 mmol, 1.2 eq) in acetonitrile (20 mL) and acetic acid (4 mL) was stirred at 100 °C for 3 h. The mixture was concentrated to dryness. The residual was treated with EA (10 mL). The mixture was stirred at 25 °C for 5 min and filtered to collect the solid which was dried to the title compound (556 mg, 1.24 mmol, 69.24% yield) as a brown solid. MS (ESI, m/z): 448.5[M-H]-.
69.24% With glacial acetic acid In acetonitrile at 100℃; for 3h; Inert atmosphere; 41.2 4-[[3-[4-(Cyanomethoxy)-2,3-difluoro-phenyl]imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethyl- benzoic acid A mixture of 2-[4-(8-chloroimidazo[1,2-a]pyrazin-3-yl)-2,3-difluoro-phenoxy]acetonitrile (573.0 mg, 1.79 mmol, 1 eq) and 4-amino-2-ethyl-benzoic acid (354.2 mg, 2.14 mmol, 1.2 eq) in acetonitrile (20 mL) and acetic acid (4 mL) was stirred at 100 °C for 3 h. The mixture was concentrated to dryness. The residual was treated with EA (10 mL). The mixture was stirred at 25 °C for 5 min and filtered to collect the solid which was dried to the title compound (556 mg, 1.24 mmol, 69.24% yield) as a brown solid. MS (ESI, m/z): 448.5[M-H]-.
  • 24
  • [ 2486-74-0 ]
  • tert-butyl 4-[[[2-ethyl-4-[(3-iodoimidazo[1,2-a]pyrazin-8-yl)amino]benzoyl]amino]methyl]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C
  • 25
  • [ 2486-74-0 ]
  • 2-ethyl-4-((3-iodoimidazo[1,2-a]pyrazin-8-yl)amino)-N-(piperidin-4-ylmethyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C
  • 26
  • [ 2486-74-0 ]
  • tert-butyl 3-[[4-[[[2-ethyl-4-[(3-iodoimidazo[1,2-a]pyrazin-8-yl)amino]benzoyl]amino]methyl]-1-piperidyl]methyl]azetidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C
  • 27
  • [ 2486-74-0 ]
  • tert-butyl 2-[4-[[[2-ethyl-4-[(3-iodoimidazo[1,2-a]pyrazin-8-yl)amino]benzoyl]amino]methyl]-1-piperidyl]acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
  • 28
  • [ 2486-74-0 ]
  • N-[[1-(2-amino-2-oxo-ethyl)-4-piperidyl]methyl]-2-ethyl-4-[(3-iodoimidazo[1,2-a]pyrazin-8-yl)amino]benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C
  • 29
  • [ 2486-74-0 ]
  • tert-butyl 3-[[4-[[[4-[[3-[2,3-difluoro-4-[3-methyl-1-(2-trimethylsilylethoxymethyl)pyrazol-4-yl]phenyl]imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethylbenzoyl]amino]methyl]-1-piperidyl]methyl]azetidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere; Microwave irradiation
Multi-step reaction with 5 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere; Sealed tube
  • 30
  • [ 2486-74-0 ]
  • tert-butyl 3-[[4-[[[4-[[3-(6-chloro-2-fluoro-3-pyridyl)imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethylbenzoyl]amino]methyl]-1-piperidyl]methyl]azetidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere
Multi-step reaction with 5 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere; Sealed tube
  • 31
  • [ 2486-74-0 ]
  • tert-butyl 3-[[4-[[[2-ethyl-4-[[3-[2-fluoro-6-(3-methyl-1H-pyrazol-4-yl)-3-pyridyl]imidazo[1,2-a]pyrazin-8-yl]amino]benzoyl]amino]methyl]-1-piperidyl]methyl]azetidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 6: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 2 h / 110 °C / Inert atmosphere
Multi-step reaction with 6 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere; Sealed tube 6: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 2 h / 110 °C / Inert atmosphere; Sealed tube
  • 32
  • [ 2486-74-0 ]
  • N-[[1-(azetidin-3-ylmethyl)-4-piperidyl]methyl]-4-[[3-[2,3-difluoro-4-(3-methyl-1H-pyrazol-4-yl)phenyl]imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethylbenzamide; formic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere; Microwave irradiation 6: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 33
  • [ 2486-74-0 ]
  • N-[[1-(azetidin-3-ylmethyl)-1-methylpiperidin-1-ium-4-yl]methyl]-2-ethyl-4-[[3-[2-fluoro-6-(3-methyl-1H-pyrazol-4-yl)-3-pyridyl]imidazo[1,2-a]pyrazin-8-yl]amino]benzamide; formic acid; formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 6: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 2 h / 110 °C / Inert atmosphere 7: N-ethyl-N,N-diisopropylamine; dmap / tetrahydrofuran / 2 h / 50 °C 8: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 45 °C 9: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C
  • 34
  • [ 2486-74-0 ]
  • tert-butyl 4-(5-(8-((4-(((1-((1-(tert-butoxycarbonyl)azetidin-3-yl)methyl)piperidin-4-yl)methyl)carbamoyl)-3-ethylphenyl)amino)imidazo[1,2-a]pyrazin-3-yl)-6-fluoropyridin-2-yl)-3-methyl-1H-pyrazole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 6: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 2 h / 110 °C / Inert atmosphere 7: N-ethyl-N,N-diisopropylamine; dmap / tetrahydrofuran / 2 h / 50 °C
Multi-step reaction with 7 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere; Sealed tube 6: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 2 h / 110 °C / Inert atmosphere; Sealed tube 7: N-ethyl-N,N-diisopropylamine; dmap / tetrahydrofuran / 2 h / 50 °C
  • 35
  • [ 2486-74-0 ]
  • tert-butyl 3-[[4-[[[4-[[3-[6-(1,3-dimethylpyrazol-4-yl)-2-fluoro-3-pyridyl]imidazo[1,2-a]pyrazin-8-yl]amino]-2-ethylbenzoyl]amino]methyl]-1-methylpiperidin-1-ium-1-yl]methyl]azetidine-1-carboxylate; iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 6: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 2 h / 110 °C / Inert atmosphere 7: N-ethyl-N,N-diisopropylamine; dmap / tetrahydrofuran / 2 h / 50 °C 8: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 45 °C
Multi-step reaction with 8 steps 1: acetic acid / acetonitrile / 18 h / 100 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C 4: sodium cyanoborohydride / methanol / 3 h / 45 °C 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere; Sealed tube 6: sodium carbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; 1,4-dioxane / 2 h / 110 °C / Inert atmosphere; Sealed tube 7: N-ethyl-N,N-diisopropylamine; dmap / tetrahydrofuran / 2 h / 50 °C 8: N-ethyl-N,N-diisopropylamine / acetonitrile / 1 h / 45 °C
  • 36
  • [ 2486-74-0 ]
  • N-[4-(3-aminopropylcarbamoyl)-3-ethylphenyl]-5-[4-(difluoromethoxy)-2,3-difluoro-phenyl]-1-methylimidazole-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 10 h 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 10 h 3.1: anhydrous sodium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / water monomer; 1,4-dioxane / 4 h / 100 °C 4.1: hydrogenchloride / tetrahydrofuran; water monomer / 5 h / 20 °C
  • 37
  • [ 2486-74-0 ]
  • tert-butyl N-[3-[[4-[(5-bromo-1-methylimidazole-2-carbonyl)amino]-2-ethyl-benzoyl]amino]propyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 10 h 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 10 h
  • 38
  • [ 2486-74-0 ]
  • tert-butyl N-[3-[[4-[[5-[4-(difluoromethoxy)-2,3-difluorophenyl]-1-methylimidazole-2-carbonyl]amino]-2-ethylbenzoyl]amino]propyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 1.2: 10 h 2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C 2.2: 10 h 3.1: anhydrous sodium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / water monomer; 1,4-dioxane / 4 h / 100 °C
  • 39
  • [ 2486-74-0 ]
  • [ 75178-96-0 ]
  • tert-butyl N-[3-[(4-amino-2-ethylbenzoyl)amino]propyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.2 g Stage #1: 4-amino-2-ethylbenzoic acid; N-tert-butoxycarbonyl-3-aminopropanamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: With O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate In N,N-dimethyl-formamide for 10h; Step 1: tert-butyl N-[3-[(4-amino-2-ethyl-benzoyl)amino]propyl]carbamate To a solution of intermediate 4-amino-2-ethylbenzoic acid (825 mg, 5.0 mmol), tert-butyl (3-aminopropyl) carbamate (1.30 g, 7.5 mmol) in anhydrous DMF (15 mL) was added DIPEA (1.30 g, 10 mmol) and then the resultant mixture was stirred for 10 min at room temperature, HATU (2.85 g, 7.5 mmol) was added in the mixture and stirred for extra 10 hr.The mixture was poured into water (50 mL) and the aqueous solution was extracted with DCM (100 mL X 2). The organic layers were combined and washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a red oil which was purified by flash column to afford tert-butyl N-[3-[(4-amino-2-ethyl-benzoyl)amino]propyl] carbamate (1.2 g) as a yellow oil. MS [M+H]+: 322.2
1.2 g Stage #1: 4-amino-2-ethylbenzoic acid; N-tert-butoxycarbonyl-3-aminopropanamine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: With O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate In N,N-dimethyl-formamide for 10h; Step 1: tert-butyl N-[3-[(4-amino-2-ethyl-benzoyl)amino]propyl]carbamate To a solution of intermediate 4-amino-2-ethylbenzoic acid (825 mg, 5.0 mmol), tert-butyl (3-aminopropyl) carbamate (1.30 g, 7.5 mmol) in anhydrous DMF (15 mL) was added DIPEA (1.30 g, 10 mmol) and then the resultant mixture was stirred for 10 min at room temperature, HATU (2.85 g, 7.5 mmol) was added in the mixture and stirred for extra 10 hr.The mixture was poured into water (50 mL) and the aqueous solution was extracted with DCM (100 mL X 2). The organic layers were combined and washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a red oil which was purified by flash column to afford tert-butyl N-[3-[(4-amino-2-ethyl-benzoyl)amino]propyl] carbamate (1.2 g) as a yellow oil. MS [M+H]+: 322.2
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