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[ CAS No. 1951483-29-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1951483-29-6
Chemical Structure| 1951483-29-6
Structure of 1951483-29-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1951483-29-6 ]

CAS No. :1951483-29-6 MDL No. :MFCD31544324
Formula : C22H27N7O2S Boiling Point : -
Linear Structure Formula :- InChI Key :JNPRPMBJODOFEC-UHFFFAOYSA-N
M.W : 453.56 Pubchem ID :121408882
Synonyms :
LY3214996

Calculated chemistry of [ 1951483-29-6 ]

Physicochemical Properties

Num. heavy atoms : 32
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.45
Num. rotatable bonds : 6
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 131.11
TPSA : 116.65 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -8.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.48
Log Po/w (XLOGP3) : 1.42
Log Po/w (WLOGP) : 1.84
Log Po/w (MLOGP) : 0.77
Log Po/w (SILICOS-IT) : 2.74
Consensus Log Po/w : 2.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.52
Solubility : 0.137 mg/ml ; 0.000302 mol/l
Class : Soluble
Log S (Ali) : -3.47
Solubility : 0.152 mg/ml ; 0.000335 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.81
Solubility : 0.000696 mg/ml ; 0.00000153 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.01

Safety of [ 1951483-29-6 ]

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 [ 1951483-29-6 ]

* 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 [ 1951483-29-6 ]

[ 1951483-29-6 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 1951483-73-0 ]
  • [ 1951483-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: ammonium hydroxide / 4 h / 200 °C / Autoclave 2: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 3: sodium hydroxide; tetra-(n-butyl)ammonium iodide / 1,4-dioxane; water / 1 h / 80 °C 4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 90 °C / Inert atmosphere 5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 90 °C / Inert atmosphere 6: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 8 steps 1: ammonium hydroxide / 4 h / 200 °C / Autoclave 2: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 3: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C / Inert atmosphere 5: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere 6: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 7: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 8: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 5 steps 1.1: ammonium hydroxide / 4 h / 200 °C / Autoclave 2.1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 3.1: sodium hydroxide; tetra-(n-butyl)ammonium iodide / 1,4-dioxane; water / 1 h / 80 °C 4.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 90 °C 4.2: 1 h / 50 - 90 °C 5.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
Multi-step reaction with 8 steps 1.1: ammonium hydroxide / 4 h / 200 °C / Autoclave 2.1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 3.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 4.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C 5.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1.5 h / 87 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 7.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h 7.2: 0 - 20 °C 8.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
Multi-step reaction with 9 steps 1.1: ammonium hydroxide / 4 h / 200 °C / Autoclave 2.1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 3.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 4.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C 5.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1.5 h / 87 °C 6.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 7.1: hydrogenchloride / 1,4-dioxane / 20 - 30 °C 8.1: tetra-(n-butyl)ammonium iodide; sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 0.17 h / 0 °C 8.2: 4 h / Cooling 9.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C

  • 2
  • [ 1951483-74-1 ]
  • [ 1951483-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 2: sodium hydroxide; tetra-(n-butyl)ammonium iodide / 1,4-dioxane; water / 1 h / 80 °C 3: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 90 °C / Inert atmosphere 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 90 °C / Inert atmosphere 5: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 7 steps 1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 2: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 3: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C / Inert atmosphere 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere 5: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 6: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 7: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 2.1: sodium hydroxide; tetra-(n-butyl)ammonium iodide / 1,4-dioxane; water / 1 h / 80 °C 3.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 90 °C 3.2: 1 h / 50 - 90 °C 4.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 2.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 3.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1.5 h / 87 °C 5.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 6.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h 6.2: 0 - 20 °C 7.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
Multi-step reaction with 8 steps 1.1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 2.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 3.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1.5 h / 87 °C 5.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 6.1: hydrogenchloride / 1,4-dioxane / 20 - 30 °C 7.1: tetra-(n-butyl)ammonium iodide; sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 0.17 h / 0 °C 7.2: 4 h / Cooling 8.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C

  • 3
  • [ 1951483-76-3 ]
  • [ 1951483-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydroxide; tetra-(n-butyl)ammonium iodide / 1,4-dioxane; water / 1 h / 80 °C 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 90 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 90 °C / Inert atmosphere 4: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 6 steps 1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C / Inert atmosphere 3: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 5: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 6: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: sodium hydroxide; tetra-(n-butyl)ammonium iodide / 1,4-dioxane; water / 1 h / 80 °C 2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 90 °C 2.2: 1 h / 50 - 90 °C 3.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
Multi-step reaction with 6 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C 3.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1.5 h / 87 °C 4.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 5.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h 5.2: 0 - 20 °C 6.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
Multi-step reaction with 7 steps 1.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C 3.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1.5 h / 87 °C 4.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 5.1: hydrogenchloride / 1,4-dioxane / 20 - 30 °C 6.1: tetra-(n-butyl)ammonium iodide; sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 0.17 h / 0 °C 6.2: 4 h / Cooling 7.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C

  • 4
  • [ 88-13-1 ]
  • [ 1951483-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -70 - -55 °C 1.2: 3 h / -70 - 0 °C 2.1: ammonium hydroxide / 4 h / 200 °C / Autoclave 3.1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 4.1: sodium hydroxide; tetra-(n-butyl)ammonium iodide / 1,4-dioxane; water / 1 h / 80 °C 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 90 °C / Inert atmosphere 6.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 90 °C / Inert atmosphere 7.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 9 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -70 - -55 °C 1.2: 3 h / -70 - 0 °C 2.1: ammonium hydroxide / 4 h / 200 °C / Autoclave 3.1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C / Inert atmosphere 6.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 8.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 9.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 10 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -70 - -55 °C 1.2: 3 h / -70 - 0 °C 1.3: 16 h / 100 °C 2.1: ammonium hydroxide / 4 h / 200 °C / Autoclave 3.1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C 6.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1.5 h / 87 °C 7.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 8.1: hydrogenchloride / 1,4-dioxane / 20 - 30 °C 9.1: tetra-(n-butyl)ammonium iodide; sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 0.17 h / 0 °C 9.2: 4 h / Cooling 10.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
Multi-step reaction with 6 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -70 - -55 °C 1.2: 3 h / -70 - 0 °C 1.3: 16 h / 100 °C 2.1: ammonium hydroxide / 4 h / 200 °C / Autoclave 3.1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 4.1: sodium hydroxide; tetra-(n-butyl)ammonium iodide / 1,4-dioxane; water / 1 h / 80 °C 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 90 °C 5.2: 1 h / 50 - 90 °C 6.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
Multi-step reaction with 9 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -70 - -55 °C 1.2: 3 h / -70 - 0 °C 1.3: 16 h / 100 °C 2.1: ammonium hydroxide / 4 h / 200 °C / Autoclave 3.1: N-Bromosuccinimide / acetonitrile / 6 h / 10 - 25 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / acetonitrile / 20 °C 5.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C 6.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1.5 h / 87 °C 7.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 8.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h 8.2: 0 - 20 °C 9.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C

  • 5
  • [ 1951483-78-5 ]
  • [ 1951483-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 4: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 5: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 5 steps 1.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1.5 h / 87 °C 3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 4.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h 4.2: 0 - 20 °C 5.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
Multi-step reaction with 6 steps 1.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 4 h / 90 °C 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1.5 h / 87 °C 3.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 4.1: hydrogenchloride / 1,4-dioxane / 20 - 30 °C 5.1: tetra-(n-butyl)ammonium iodide; sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 0.17 h / 0 °C 5.2: 4 h / Cooling 6.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
  • 6
  • [ 1951483-79-6 ]
  • [ 1951483-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 2 h / 90 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 4: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 4 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1.5 h / 87 °C 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h 3.2: 0 - 20 °C 4.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
Multi-step reaction with 5 steps 1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1.5 h / 87 °C 2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3.1: hydrogenchloride / 1,4-dioxane / 20 - 30 °C 4.1: tetra-(n-butyl)ammonium iodide; sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 0.17 h / 0 °C 4.2: 4 h / Cooling 5.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
  • 7
  • [ 1951483-80-9 ]
  • [ 1951483-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 3: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h 2.2: 0 - 20 °C 3.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
Multi-step reaction with 4 steps 1.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 2.1: hydrogenchloride / 1,4-dioxane / 20 - 30 °C 3.1: tetra-(n-butyl)ammonium iodide; sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 0.17 h / 0 °C 3.2: 4 h / Cooling 4.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
  • 8
  • [ 1951483-81-0 ]
  • [ 1951483-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C 2: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.17 h 1.2: 0 - 20 °C 2.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
Multi-step reaction with 3 steps 1.1: hydrogenchloride / 1,4-dioxane / 20 - 30 °C 2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 0.17 h / 0 °C 2.2: 4 h / Cooling 3.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
  • 9
  • [ CAS Unavailable ]
  • [ 1951483-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 90 °C / Inert atmosphere 2: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
  • 10
  • [ 622-40-2 ]
  • [ 1951483-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dibromotriphenylphosphorane / dichloromethane / 1 h / 25 °C 2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.17 h / 0 °C 2.2: 4 h / 0 - 20 °C 3.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: dibromotriphenylphosphorane / dichloromethane / 20 - 25 °C 2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / mineral oil; 1-methyl-pyrrolidin-2-one / 0.17 h / 0 °C 2.2: 4 h / Cooling 3.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
  • 11
  • [ 42802-94-8 ]
  • 6,6-dimethyl-2-{2-[(1-methyl-1H-pyrazol-5-yl)amino]pyrimidin-4-yl}-5-[2-(morpholin-4-yl)ethyl]-5,6-dihydro-4H-thieno[2,3-c]pyrrol-4-one [ No CAS ]
  • 12
  • [ 1951483-83-2 ]
  • [ 1951483-29-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 90 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1 h / 90 °C / Inert atmosphere 3: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / 1,4-dioxane / 90 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1 h / 90 °C 1.2: 1 h / 50 - 90 °C 2.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 85 °C
  • 13
  • [ 1951483-93-4 ]
  • [ 1192-21-8 ]
  • [ 1951483-29-6 ]
YieldReaction ConditionsOperation in experiment
48% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 85℃; Synthetic method 2: Degas a mixture of 2-(2-chloropyrimidin-4-yl)-6,6-dimethyl-5-(2- morpholinoethyl)thieno[2,3-c]pyrrol-4-one (20.8 g, 52.9 mmol), 2-methylpyrazol-3-amine (5.7 g, 58.2 mmol), cesium carbonate (37.9 g, 116.5 mmol), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (2.6 g, 4.5 mmol) and 1,4-dioxane (529 mL) with nitrogen for 10 minutes. Add tris(dibenzylideneacetone)dipalladium(0) (2.4 g, 2.6 mmol) and heat the mixture to 85 °C for four hours. Cool the mixture to room temperature and filter the mixture through filter paper. Concentrate the filtrate under reduced pressure. Repeat the reaction starting with 8 g of 2-(2-chloropyrimidin-4-yl)-6,6- dimethyl-5-(2-morpholinoethyl)thieno[2,3-c]pyrrol-4-one and combine the two residues. Purify the residue by silica gel column chromatography (330 g) eluting with a gradient from 5-25% MeOH in (10% EtOAc in DCM). Pool the fractions and concentrate under reduced pressure. Re-purify the residue by silica gel column chromatography (330 g) eluting with a gradient from 5-25% MeOH in 10% EtOAc in DCM. Pool the fractions and concentrate under reduced pressure. Dissolve the residue in DCM (400 mL) and then add acetone (1 L). Slowly concentrate the mixture under reduced pressure to approximately 700 mL. Collect the solid by vacuum filtration to give the title compound 14.8 g (48%). MS (m/z): 454 (M+1).
18% With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 90℃; Inert atmosphere; 1.3 Synthetic Method 3: Degas a mixture of 2-(2-chloropyrimidin-4-yl)-6,6-dimethyl-5-(2-morpholinoethyl)thieno[2,3-c]pyrrol-4-one (250 mg, 0.64 mmol), 2-methylpyrazol-3-amine (124 mg, 1.3 mmol), cesium carbonate (622 mg, 1.9 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (55 mg, 0.095 mmol) and 1,4-dioxane (6.4 mL) with nitrogen for 15 minutes. Add palladium(II)acetate (14.3 mg, 0.0636 mmol) and heat the mixture at 90° C. overnight. Cool the mixture to room temperature and filter the mixture through filter paper. Wash the solids with 10% MeOH in DCM. Concentrate the filtrate under reduced pressure. Repeat the reaction and combine the two residues. Purify the residue by HPLC on a C18 column (30×75 mm, 5 um, xbridge ODB) eluting with a 85 mL/minute gradient from 9-28% ACN in 10 mM ammonium carbonate (pH 10) in water. Pool the fractions and concentrate under reduced pressure to remove the ACN. Lyophilize the aqueous solution to give the title compound 100 mg (18%). MS (m/z): 454 (M+1).
  • 14
  • 2-(2-chloropyrimidin-4-yl)-6,6-dimethyl-5H-thieno[2,3-c]pyrrol-4-one hydrochloride [ No CAS ]
  • [ 42802-94-8 ]
  • 6,6-dimethyl-2-{2-[(1-methyl-1H-pyrazol-5-yl)amino]pyrimidin-4-yl}-5-[2-(morpholin-4-yl)ethyl]-5,6-dihydro-4H-thieno[2,3-c]pyrrol-4-one [ No CAS ]
  • 15
  • [ 1951483-29-6 ]
  • [ 2365171-03-3 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride In methanol; water at 20℃; for 0.333333h; Sonication; 4 Reference Example 4 6,6-Dimethyl-2-{2-[(l-methyl-lH-pyrazol-5-yl)amino]pyrimidin-4-yl}-5-[2-(morpholin- 4-yl)ethyl]-5,6-dihydro-4H-thieno[2,3-c]pyrrol-4-one; hydrochloride Concentrated hydrochloric acid (10 mL, 120 mmol) is slowly added to a solution of 6, 6-dimethyl-2-{2-[(l -methyl- lH-pyrazol-5-yl)amino]pyrimidin-4-yl }-5-[2- (morpholin-4-yl)ethyl]-5,6-dihydro-4H-thieno[2,3-c]pyrrol-4-one (500 mg, 1.10 mmol) in MeOH (50 mL). The mixture is sonicated for 20 minutes at room temperature. The reaction is concentrated under vacuum to give the title compound (531 mg, 98%). MS (m/z): 454 (M+l).
  • 16
  • [ 75-75-2 ]
  • [ 1951483-29-6 ]
  • [ 2365171-00-0 ]
YieldReaction ConditionsOperation in experiment
100% In methanol; dichloromethane at 20℃; for 0.5h; Sonication; 1 Alternate Preparation of Example 1 6.6-Dimethyl-2-{2-[(l-methyl-lH-pyrazol-5-yl)amino]pyrimidin-4-yl}-5-[2-(morpholin-4-yl)ethyl]-5,6-dihydro-4H-thieno[2,3-c]pyrrol-4-one; methanesulfonic acid Methanesulfonic acid (110 mg, 1.14 mmol) is added to a solution of 6,6-dimethyl- 2-{2-[(l -methyl- lH-pyrazol-5-yl)amino]pyrimidin-4-yl}-5-[2-(morpholin-4-yl)ethyl]-5.6-dihydro-4H-thieno[2,3-c]pyrrol-4-one (518 mg, 1.14 mmol) in a mixture of MeOH (6 mL) and DCM (6 mL). The mixture is sonicated for 30 minutes at room temperature. The reaction is concentrated under vacuum to give the title compound (633 mg, 100%). MS (m/z): 454 (M+l).
633 mg In methanol; dichloromethane at 20℃; for 0.5h; 1 6, 6-Dimethyl -2-{2-[(l-m ethyl-lH-pyrazol-5-yl)amino]pyrimidin-4-yl }-5-[2-(morpholin- 4-yl)ethyl]-5,6-dihydro-4H-thieno[2,3-c]pyrrol-4-one; methanesulfonic acid Methanesulfonic acid (110 mg, 1.14 mmol) is added to a solution of Example A (518 mg, 1.14 mmol) in a mixture of MeOH (6 mL) and DCM (6 mL). The mixture is sonicated for 30 minutes at room temperature. The reaction is concentrated under vacuum to give the title compound (633 mg, 100%). MS (m/z): 454 (M+l).
  • 17
  • [ 1951483-29-6 ]
  • [ 104-15-4 ]
  • [ 2365171-02-2 ]
YieldReaction ConditionsOperation in experiment
100% In dichloromethane at 20℃; for 0.5h; Sonication; 3 Alternate Preparation of Example 3 6,6-Dimethyl-2-{2-[(l-methyl-lH-pyrazol-5-yl)amino]pyrimidin-4-yl}-5-[2-(morpholin- 4-yl)ethyl]-5,6-dihydro-4H-thieno[2,3-c]pyrrol-4-one; 4-methylbenzenesulfonic acid 4-Methylbenzenesulfonic acid monohydrate (216 mg, 1.14 mmol) is dissolved in DCM (3 mL) and added to a solution of 6,6-dimethyl-2-{2-[(l-methyl-lH-pyrazol-5- yl)amino]pyrimidin-4-yl}-5-[2-(morpholin-4-yl)ethyl]-5,6-dihydro-4H-thieno[2,3- c]pyrrol-4-one (516 mg, 1.14 mmol) in DCM (3 mL). Sonicate the mixture for 30 minutes at room temperature. Concentrate the reaction under vacuum to give the title compound (708 mg, 100%). MS (m/z): 454 (M+l) and 171 (M+l).
In ethanol; water; ethyl acetate at 70℃; for 0.5h; 3 6, 6-Dimethyl -2-{2-[(l-methyl-lH-pyrazol-5-yl)amino]pyrimidin-4-yl}-5-[2-(morpholin- 4-yl)ethyl]-5,6-dihydro-4H-thieno[2,3-c]pyrrol-4-one; 4-methylbenzenesulfonic acid Example A (1125 mg, 2.5 mmol) in 95% ethanol (10 mL) and the mixture is stirred at 70 °C at 1000 rpm. 4-Toluenesulfonic acid (460 mg, 2.7 mmol) is dissolved in EtOAc (5 mL) and the initial slurry becomes a gummy yellow solid. The mixture is stirred for 30 minutes and a white solid results. The solid is collected by filtration and dried at 60 °C under vacuum to give the title compound.
  • 18
  • [ 75-75-2 ]
  • [ 1951483-29-6 ]
  • [ 2365171-01-1 ]
YieldReaction ConditionsOperation in experiment
13.4 g With water In ethanol at 50 - 70℃; for 2h; 2 Example 2 6, 6-Dimethyl -2-{2-[(l-methyl-lH-pyrazol-5-yl)amino]pyrimidin-4-yl}-5-[2-(morpholin- 4-yl)ethyl]-5,6-dihydro-4H-thieno[2,3-c]pyrrol-4-one; methanesulfonic acid dihydrate Example A (16.07 g, 35.4 mmol) is suspended in 90% ethanol, stirred and heated to 70 °C. Additional ethanol (100 mL) is added to give a solution. Methanesulfonic acid (3.75 g, 39 mmol) is added dropwise and rinsed in with 90% ethanol (2 mL). The mixture is cooled to 60 °C and seeds of the title compound are added which dissolved upon addition. The addition of seeds is repeated at 50 °C. The mixture is stirred at 50 °C for 2 hrs and then cooled to room temperature. The resulting precipitate is isolated by filtration and allowed to air dry to give the title compound (13.4 g, 70%).
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