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[ CAS No. 878741-84-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 878741-84-5
Chemical Structure| 878741-84-5
Chemical Structure| 878741-84-5
Structure of 878741-84-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 878741-84-5 ]

CAS No. :878741-84-5 MDL No. :MFCD18378610
Formula : C10H8BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :HHMMDHGCCRYVID-UHFFFAOYSA-N
M.W : 254.08 Pubchem ID :68955467
Synonyms :

Calculated chemistry of [ 878741-84-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.94
TPSA : 50.09 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) : -6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.22
Log Po/w (XLOGP3) : 2.12
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 2.29
Log Po/w (SILICOS-IT) : 2.73
Consensus Log Po/w : 2.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.343 mg/ml ; 0.00135 mol/l
Class : Soluble
Log S (Ali) : -2.8
Solubility : 0.4 mg/ml ; 0.00157 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.82
Solubility : 0.0384 mg/ml ; 0.000151 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.85

Safety of [ 878741-84-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 878741-84-5 ]

* 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 [ 878741-84-5 ]

[ 878741-84-5 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 878741-84-5 ]
  • [ 74-88-4 ]
  • [ 878742-12-2 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: methyl 3-bromo-5-(cyanomethyl)benzoate With sodium hydride In dimethyl sulfoxide at 20℃; Stage #2: methyl iodide In dimethyl sulfoxide at 0 - 25℃; for 12h; 131 Method 131; Methyl 3 -bromo-5 -( 1 -cyano- 1 -methy lethy Dbenzoate; A solution of methyl 3-bromo-5-(cyanomethyl)benzoate (Method 30; 600 mg, 2.36 mmol) in anhydrous DMSO (12 ml) was treated with sodium hydride (60%, 284 mg, 7.09 mmol). Iodomethane (0.882 ml, 14.17 mmol) was then added dropwise at 0 °C. The reaction mixture was stirred at 25 °C for 12 h. The reaction mixture was then quenched with water (200 ml) and extracted with EtOAc. The combined organics were dried and concentrated under reduced pressure. The crude product was purified by column chromatography utilizing an ISCO system (hexane-EtOAc) to give 635 mg (95%) of a clear oil; NMR (300 MHz): 7.92 (s, IH), 7.83 (s, IH), 7.55 (s, IH), 3.94 (s, 3H), 1.76 (s, 6H).
  • 4
  • [ 877624-40-3 ]
  • [ 10442-39-4 ]
  • [ 878741-84-5 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 70℃; tetrabutylammonium cyanide (50 g) was added to Example 1.21.1 (67.1 g) in 300 mL acetonitrile, and the mixture was heated to 70 C. overnight. The mixture was cooled, poured into diethyl ether, and rinsed with water and brine. The mixture was concentrated and chromatographed on silica gel using 2-20% ethyl acetate in heptane to give the title compound.
In acetonitrile; at 70℃; [000802] Tetrabutylammonium cyanide (50 g) was added to Example 1.75.1 (67.1 g) in 300 mL acetonitrile, and the mixture was heated to 70C overnight. The mixture was cooled, poured into diethyl ether, and rinsed with water and brine. The mixture was then concentrated and chromatographed on silica gel using 2-20% ethyl acetate in heptanes to give the title compound.
In acetonitrile; at 70℃; Tetrabutylammonium cyanide (50 g) was added to Example 1.21.1 (67.1 g) in 300 mL acetonitrile, and the mixture was heated to 70 C overnight. The mixture was cooled, poured into diethyl ether, and rinsed with water and brine. The mixture was concentrated and chromatographed on silica gel using 2-20% ethyl acetate in heptane to give the title compound.
In acetonitrile; at 70℃; Tetrabutylammonium cyanide (50 g) was added to Example 1.21.1 (67.1 g) in 300 mLacetonitrile, and the mixture was heated to 70 oc overnight. The mixture was cooled, poured intodiethyl ether, and rinsed with water and brine. The mixture was concentrated and chromatographedon silica gel using 2-20% ethyl acetate in heptane to give the title compound
In acetonitrile; at 70℃; Tetrabutylammonium cyanide (50 g) was added to Example 1.75.1 (67.1 g) in 300 mL acetonitrile, and the mixture was heated to 70oC overnight. The mixture was cooled, poured into diethyl ether, and rinsed with water and brine. The mixture was then concentrated and chromatographed on silica gel using 2-20% ethyl acetate in heptanes to give the title compound.
In acetonitrile; at 70℃; Tetrabutylammonium cyanide (50 g) was added to Example 1.75.1 (67.1 g) in 300 mLacetonitrile, and the mixture was heated to 70C overnight. The mixture was cooled, poured intodiethyl ether, and rinsed with water and brine. The mixture was then concentrated and20 chromatographed on silica gel using 2-20% ethyl acetate in heptanes to give the title compound
In acetonitrile; at 70℃; Tetrabutylammonium cyanide (50 g) was added to Example 1.75.1 (67.1 g) in 300 mL acetonitrile, and the mixture was heated to 70 C. overnight. The mixture was cooled, poured into diethyl ether, and rinsed with water and brine. The mixture was then concentrated and chromatographed on silica gel using 2-20% ethyl acetate in heptanes to give the title compound.

  • 5
  • [ 878741-84-5 ]
  • methyl 3-(2-aminoethyl)-5-bromobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With borane-THF In tetrahydrofuran 1.21.3 1.21.3 methyl 3-(2-aminoethyl)-5-bromobenzoate borane-tetrahydrofuran complex (126 mL, 1M solution) was added to a solution of Example 1.21.2 (16 g) in 200 mL tetrahydrofuran, and the mixture was stirred overnight. The reaction was carefully quenched with methanol (50 mL), and then concentrated to 50 mL volume. The mixture was then taken up in 120 mL methanol/120 mL 4M HCl/120 mL dioxane, and stirred overnight. The organics were removed by evaporation under reduced pressure, and the residue was extracted with diethyl ether (2×). The organic extracts were discarded. The aqueous layer was basified with solid K2CO3, and then extracted with ethyl acetate, and dichloromethane (2×). The extracts were combined, dried over Na2SO4, filtered and concentrated to give the title compound.
With borane-THF In tetrahydrofuran at 70℃; 1.1.75.1.75.3 1.75.3 methyl 3-(2-aminoethyl)-5-bromobenzoate [000803] Borane-THF complex (126 mL, 1M solution) was added to a solution of Example 1.75.2 (16 g) in 200 mL tetrahydrofuran, and the mixture was stirred overnight. The reaction was carefully quenched with methanol (50 mL), and then concentrated to 50 mL volume. The mixture was taken up in 120 mL methanol / 120 mL 4M HC1 / 120 mL dioxane, and stirred overnight. The organics were removed under reduced pressure, and the residue was extracted twice with diethyl ether. The extracts were discarded. The organic layer was basified with solid K2CO3, and then extracted with ethyl acetate, and dichloromethane (2x). The extracts were combined, dried over NaaSOzi, filtered and concentrated to give the title compound.
With borane-THF In tetrahydrofuran 1.1.21.1.21.3 1.21.3 methyl 3-(2-aminoethyl)-5-bromobenzoate Borane-tetrahydrofuran complex (126 mL, 1M solution) was added to a solution of Example 1.21.2 (16 g) in 200 mL tetrahydrofuran, and the mixture was stirred overnight. The reaction was carefully quenched with methanol (50 mL), and then concentrated to 50 mL volume. The mixture was then taken up in 120 mL methanol / 120 mL 4M HC1 / 120 mL dioxane, and stirred overnight. The organics were removed by evaporation under reduced pressure, and the residue was extracted with diethyl ether (2 x). The organic extracts were discarded. The aqueous layer was basified with solid K2CO3, and then extracted with ethyl acetate, and dichloromethane (2x). The extracts were combined, dried over Na2S04, filtered and concentrated to give the title compound.
With borane-THF In tetrahydrofuran 1.21.3 1.21.3 methyl 3-(2-aminoethyl)-5-bromobenzoate Borane-tetrahydrofuran complex (126 mL, 1M solution) was added to a solution of Example1.21.2 (16 g) in 200 mL tetrahydrofuran, and the mixture was stirred overnight. The reaction wascarefully quenched with methanol (50 mL), and then concentrated to 50 mL volume. The mixturewas then taken up in 120 mL methanol I 120 mL 4M HCl I 120 mL dioxane, and stirred overnight.The organics were removed by evaporation under reduced pressure, and the residue was extracted15 with diethyl ether (2 x). The organic extracts were discarded. The aqueous layer was basified withsolid K2C03 , and then extracted with ethyl acetate, and dichloromethane (2x). The extracts werecombined, dried over Na2S04 , filtered and concentrated to give the title compound
With borane-THF In tetrahydrofuran 1.1.75.1.75.3 1.75.3 methyl 3-(2-aminoethyl)-5-bromobenzoate Borane-THF complex (126 mL, 1M solution) was added to a solution of Example 1.75.2 (16 g) in 200 mL tetrahydrofuran, and the mixture was stirred overnight. The reaction was carefully quenched with methanol (50 mL), and then concentrated to 50 mL volume. The mixture was taken up in 120 mL methanol / 120 mL 4M HCl / 120 mL dioxane, and stirred overnight. The organics were removed under reduced pressure, and the residue was extracted twice with diethyl ether. The extracts were discarded. The organic layer was basified with solid K2CO3, and then extracted with ethyl acetate, and dichloromethane (2x). The extracts were combined, dried over Na2SO4, filtered and concentrated to give the title compound.
With borane-THF In tetrahydrofuran 1.75.3 1.75.3 methyl 3-(2-aminoethyl)-5-bromobenzoate Borane-THF complex (126 mL, 1M solution) was added to a solution of Example 1.75.2(16 g) in 200 mL tetrahydrofuran, and the mixture was stirred overnight. The reaction was carefullyquenched with methanol (50 mL), and then concentrated to 50 mL volume. The mixture was taken25 up in 120 mL methanol I 120 mL 4M HCl I 120 mL dioxane, and stirred overnight. The organicswere removed under reduced pressure, and the residue was extracted twice with diethyl ether. Theextracts were discarded. The organic layer was basified with solid K2C03 , and then extracted withethyl acetate, and dichloromethane (2x). The extracts were combined, dried over Na2S04, filteredand concentrated to give the title compound..
With borane-THF In tetrahydrofuran 1.75.3 1.75.3 methyl 3-(2-aminoethyl)-5-bromobenzoate Borane-THF complex (126 mE, 1M solution) was added to a solution of Example 1.75.2 (16 g) in 200 mE tetrahydrofuran, and the mixture was stirred overnight. The reaction was carefully quenched with methanol (50 mL), and then concentrated to 50 mL volume. The mixture was taken up in 120 mL methanol/120 mL 4M HCl/120 mL dioxane, and stirred overnight. The organics were removed under reduced pressure, and the residue was extracted twice with diethyl ether. The extracts were discarded. The organic layer was basified with solid K2C03, and then extracted with ethyl acetate, and dichloromethane (2x). The extracts were combined, dried over Na2504, filtered and concentrated to give the title compound.

  • 6
  • [ 878741-84-5 ]
  • methyl 3-bromo-5-(2-(2,2,2-trifluoroacetamido)ethyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran / 70 °C 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: borane-THF / tetrahydrofuran 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C

  • 7
  • [ 878741-84-5 ]
  • methyl 6-bromo-2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / ethyl acetate / 2 h
Multi-step reaction with 3 steps 1: borane-THF / tetrahydrofuran / 70 °C 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h
Multi-step reaction with 3 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h
Multi-step reaction with 3 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2.17 h / Cooling with ice
Multi-step reaction with 3 steps 1: borane-THF / tetrahydrofuran 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h
Multi-step reaction with 3 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h
Multi-step reaction with 3 steps 1: borane-THF / tetrahydrofuran 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h

  • 8
  • [ 878741-84-5 ]
  • methyl 6-((2-((tert-butoxycarbonyl)(methyl)amino)ethyl)(methyl)amino)-2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / ethyl acetate / 2 h 4: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 80 °C
Multi-step reaction with 4 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 80 °C
Multi-step reaction with 4 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2.17 h / Cooling with ice 4: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 80 °C
  • 9
  • [ 878741-84-5 ]
  • methyl 2-(5-bromo-6-(tert-butoxycarbonyl)pyridin-2-yl)-6-((2-((tert-butoxycarbonyl)(methyl)amino)ethyl)(methyl)amino)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: borane-THF / tetrahydrofuran 2.1: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3.1: sulfuric acid / ethyl acetate / 2 h 4.1: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 80 °C 5.1: potassium carbonate; triethylamine / water; methanol; tetrahydrofuran 5.2: 50 °C
Multi-step reaction with 6 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 80 °C 5: potassium carbonate; water / tetrahydrofuran; methanol 6: triethylamine / N,N-dimethyl-formamide / 50 °C
Multi-step reaction with 5 steps 1.1: borane-THF / tetrahydrofuran 2.1: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3.1: sulfuric acid / 2.17 h / Cooling with ice 4.1: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 80 °C 5.1: potassium carbonate / tetrahydrofuran; water; methanol 5.2: 50 °C
  • 10
  • [ 878741-84-5 ]
  • methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / ethyl acetate / 2 h 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 24 h / 70 °C
Multi-step reaction with 4 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 24 h / 70 °C
Multi-step reaction with 4 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2.17 h / Cooling with ice 4: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 24 h / 70 °C
  • 11
  • [ 878741-84-5 ]
  • methyl 6-hydroxy-2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / ethyl acetate / 2 h 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 24 h / 70 °C 5: sodium hydroxide; dihydrogen peroxide / water; tetrahydrofuran; ethyl acetate / 1.5 h
Multi-step reaction with 5 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 24 h / 70 °C 5: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 1.5 h
Multi-step reaction with 5 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2.17 h / Cooling with ice 4: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 24 h / 70 °C 5: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 1.5 h
  • 12
  • [ 878741-84-5 ]
  • methyl 6-methoxy-2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / ethyl acetate / 2 h 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 24 h / 70 °C 5: sodium hydroxide; dihydrogen peroxide / water; tetrahydrofuran; ethyl acetate / 1.5 h 6: diazomethyl-trimethyl-silane / methanol; diethyl ether / 24 h
Multi-step reaction with 6 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 24 h / 70 °C 5: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 1.5 h 6: methanol; diethyl ether / 24 h
Multi-step reaction with 6 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2.17 h / Cooling with ice 4: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 24 h / 70 °C 5: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 1.5 h 6: methanol; diethyl ether / 24 h
  • 13
  • [ 878741-84-5 ]
  • methyl 6-(3-((tert-butoxycarbonyl)(methyl)amino)prop-1-yn-1-yl)-2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: borane-THF / tetrahydrofuran / 70 °C 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C
Multi-step reaction with 4 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 50 °C
Multi-step reaction with 4 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2.17 h / Cooling with ice 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C
Multi-step reaction with 4 steps 1: borane-THF / tetrahydrofuran 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C
Multi-step reaction with 4 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C
Multi-step reaction with 4 steps 1: borane-THF / tetrahydrofuran 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 50 °C

  • 14
  • [ 878741-84-5 ]
  • methyl 6-(3-((tert-butoxycarbonyl)(methyl)amino)propyl)-2-(2,2,2-trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: borane-THF / tetrahydrofuran / 70 °C 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C 5: 20% palladium hydroxide-activated charcoal; hydrogen / tetrahydrofuran; methanol / 12 h / 50 °C / 2585.81 Torr
Multi-step reaction with 5 steps 1: borane-THF / tetrahydrofuran 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C 5: 20% palladium hydroxide-activated charcoal; hydrogen / tetrahydrofuran; methanol / 12 h / 50 °C / 2585.81 Torr
Multi-step reaction with 5 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C 5: methanol; 20% palladium hydroxide-activated charcoal / tetrahydrofuran / 12 h / 50 °C / 2585.81 Torr
Multi-step reaction with 5 steps 1: borane-THF / tetrahydrofuran 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 50 °C 5: Pd(OH)2/C / tetrahydrofuran; methanol / 12 h / 50 °C / 2585.81 Torr

  • 15
  • [ 878741-84-5 ]
  • C20H30N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: borane-THF / tetrahydrofuran / 70 °C 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C 5: 20% palladium hydroxide-activated charcoal; hydrogen / tetrahydrofuran; methanol / 12 h / 50 °C / 2585.81 Torr 6: potassium carbonate; water / tetrahydrofuran; methanol
Multi-step reaction with 6 steps 1: borane-THF / tetrahydrofuran 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C 5: 20% palladium hydroxide-activated charcoal; hydrogen / tetrahydrofuran; methanol / 12 h / 50 °C / 2585.81 Torr 6: potassium carbonate; water / tetrahydrofuran; methanol
  • 16
  • [ 878741-84-5 ]
  • methyl 2-(5-bromo-6-(tert-butoxycarbonyl)pyridin-2-yl)-6-(3-((tert-butoxycarbonyl)(methyl)amino)propyl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: borane-THF / tetrahydrofuran / 70 °C 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C 5: 20% palladium hydroxide-activated charcoal; hydrogen / tetrahydrofuran; methanol / 12 h / 50 °C / 2585.81 Torr 6: potassium carbonate; water / tetrahydrofuran; methanol 7: triethylamine / N,N-dimethyl-formamide / 60 °C
Multi-step reaction with 7 steps 1: borane-THF / tetrahydrofuran 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C 5: 20% palladium hydroxide-activated charcoal; hydrogen / tetrahydrofuran; methanol / 12 h / 50 °C / 2585.81 Torr 6: potassium carbonate; water / tetrahydrofuran; methanol 7: triethylamine / N,N-dimethyl-formamide / 60 °C
Multi-step reaction with 6 steps 1.1: borane-THF / tetrahydrofuran 2.1: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3.1: sulfuric acid / 2 h 4.1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 50 °C 5.1: Pd(OH)2/C / tetrahydrofuran; methanol / 12 h / 50 °C / 2585.81 Torr 6.1: triethylamine; potassium carbonate / tetrahydrofuran; water; methanol 6.2: 60 °C
  • 17
  • [ 878741-84-5 ]
  • methyl 6-(3-((tert-butoxycarbonyl)(methyl)amino)propyl)-2-(6-(tert-butoxycarbonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: borane-THF / tetrahydrofuran / 70 °C 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C 5: 20% palladium hydroxide-activated charcoal; hydrogen / tetrahydrofuran; methanol / 12 h / 50 °C / 2585.81 Torr 6: potassium carbonate; water / tetrahydrofuran; methanol 7: triethylamine / N,N-dimethyl-formamide / 60 °C 8: triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / acetonitrile / 60 - 75 °C
Multi-step reaction with 8 steps 1: borane-THF / tetrahydrofuran 2: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,4-dioxane / 50 °C 5: 20% palladium hydroxide-activated charcoal; hydrogen / tetrahydrofuran; methanol / 12 h / 50 °C / 2585.81 Torr 6: potassium carbonate; water / tetrahydrofuran; methanol 7: triethylamine / N,N-dimethyl-formamide / 60 °C 8: triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 60 - 75 °C
Multi-step reaction with 7 steps 1.1: borane-THF / tetrahydrofuran 2.1: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3.1: sulfuric acid / 2 h 4.1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 50 °C 5.1: Pd(OH)2/C / tetrahydrofuran; methanol / 12 h / 50 °C / 2585.81 Torr 6.1: triethylamine; potassium carbonate / tetrahydrofuran; water; methanol 6.2: 60 °C 7.1: triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 5 h / 60 - 75 °C
  • 18
  • [ 878741-84-5 ]
  • C20H31N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: borane-THF / tetrahydrofuran 2: triethylamine / dichloromethane / 72 h / 0 - 20 °C 3: sulfuric acid / 2 h 4: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 80 °C 5: potassium carbonate; water / tetrahydrofuran; methanol
  • 19
  • [ 878741-84-5 ]
  • 6-(6-(3-((tert-butoxycarbonyl)(methyl)amino)propyl)-8-(methoxycarbonyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(1-((3-(2-((2-((4-((tert-butyldiphenylsilyl)oxy)-2,2-dimethylbutoxy)sulfonyl)ethyl)amino)ethoxy)-5,7-dimethyladamantan-1-yl)methyl)-5-methyl-1H-pyrazol-4-yl)picolinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: borane-THF / tetrahydrofuran 2.1: trimethylamine / dichloromethane / 72 h / 0 - 20 °C 3.1: sulfuric acid / 2 h 4.1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 50 °C 5.1: Pd(OH)2/C / tetrahydrofuran; methanol / 12 h / 50 °C / 2585.81 Torr 6.1: triethylamine; potassium carbonate / tetrahydrofuran; water; methanol 6.2: 60 °C 7.1: triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / acetonitrile / 5 h / 60 - 75 °C 8.1: tris-(dibenzylideneacetone)dipalladium(0); 1,3,5,7-tetramethyl-6-tetradecane-2,4,8-trioxa-6-phosphaadamantane; potassium phosphate / 1,4-dioxane; water / 70 °C / Inert atmosphere
  • 20
  • [ 878741-84-5 ]
  • methyl 3-amino-5-(1-cyanocyclobutyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 16 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 2.2: 1 h
  • 21
  • [ 878741-84-5 ]
  • methyl 3-((5-bromo-2-hydroxyphenyl)sulfonamido)-5-(1-cyanocyclobutyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 16 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 2.2: 1 h 3.1: pyridine / dichloromethane / 20 °C
  • 22
  • [ 878741-84-5 ]
  • 3-((5-bromo-2-hydroxyphenyl)sulfonamido)-5-(1-cyanocyclobutyl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 16 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 2.2: 1 h 3.1: pyridine / dichloromethane / 20 °C 4.1: lithium hydroxide / tetrahydrofuran / 20 °C
  • 23
  • [ 878741-84-5 ]
  • 3-amino-5-(1-cyanocyclobutyl)-N-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 16 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 2.2: 1 h 3.1: tetrahydrofuran / 3 h / 65 °C
  • 24
  • [ 878741-84-5 ]
  • 3-((5-bromo-2-hydroxyphenyl)sulfonamido)-5-(1-cyanocyclobutyl)-N-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 16 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 2.2: 1 h 3.1: tetrahydrofuran / 3 h / 65 °C 4.1: pyridine / dichloromethane / 20 °C
  • 25
  • [ 878741-84-5 ]
  • 3-((5-bromo-3-chloro-2-hydroxyphenyl)sulfonamido)-5-(1-cyanocyclobutyl)-N-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 16 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 2.2: 1 h 3.1: tetrahydrofuran / 3 h / 65 °C 4.1: pyridine / dichloromethane / 20 °C
  • 27
  • [ 478375-40-5 ]
  • [ 7677-24-9 ]
  • [ 878741-84-5 ]
  • 28
  • [ 878741-84-5 ]
  • C28H28N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 1.3: 16 h / 20 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2.2: 18 h / 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 4.1: potassium acetate; XPhos; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / ethanol / 1 h / 80 °C / Inert atmosphere 5.1: potassium carbonate / water; ethanol / 17 h / 80 °C
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2.2: 18 h / 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 4.1: potassium acetate; XPhos; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / ethanol / 1 h / 80 °C / Inert atmosphere 5.1: potassium carbonate / water; ethanol / 17 h / 80 °C
Reference: [1]Lorthiois, Edwige; Roache, James; Barnes-Seeman, David; Altmann, Eva; Hassiepen, Ulrich; Turner, Gordon; Duvadie, Rohit; Hornak, Viktor; Karki, Rajeshri G.; Schiering, Nikolaus; Weihofen, Wilhelm A.; Perruccio, Francesca; Calhoun, Amy; Fazal, Tanzina; Dedic, Darija; Durand, Corinne; Dussauge, Solene; Fettis, Kamal; Tritsch, Fabien; Dentel, Celine; Druet, Adelaide; Liu, Donglei; Kirman, Louise; Lachal, Julie; Namoto, Kenji; Bevan, Douglas; Mo, Rose; Monnet, Gabriela; Muller, Lionel; Zessis, Richard; Huang, Xueming; Lindsley, Loren; Currie, Treeve; Chiu, Yu-Hsin; Fridrich, Cary; Delgado, Peter; Wang, Shuangxi; Hollis-Symynkywicz, Micah; Berghausen, Joerg; Williams, Eric; Liu, Hong; Liang, Guiqing; Kim, Hyungchul; Hoffmann, Peter; Hein, Andreas; Ramage, Paul; D'arcy, Allan; Harlfinger, Stefanie; Renatus, Martin; Ruedisser, Simon; Feldman, David; Elliott, Jason; Sedrani, Richard; Maibaum, Juergen; Adams, Christopher M. [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8088 - 8113]
[2]Lorthiois, Edwige; Roache, James; Barnes-Seeman, David; Altmann, Eva; Hassiepen, Ulrich; Turner, Gordon; Duvadie, Rohit; Hornak, Viktor; Karki, Rajeshri G.; Schiering, Nikolaus; Weihofen, Wilhelm A.; Perruccio, Francesca; Calhoun, Amy; Fazal, Tanzina; Dedic, Darija; Durand, Corinne; Dussauge, Solene; Fettis, Kamal; Tritsch, Fabien; Dentel, Celine; Druet, Adelaide; Liu, Donglei; Kirman, Louise; Lachal, Julie; Namoto, Kenji; Bevan, Douglas; Mo, Rose; Monnet, Gabriela; Muller, Lionel; Zessis, Richard; Huang, Xueming; Lindsley, Loren; Currie, Treeve; Chiu, Yu-Hsin; Fridrich, Cary; Delgado, Peter; Wang, Shuangxi; Hollis-Symynkywicz, Micah; Berghausen, Joerg; Williams, Eric; Liu, Hong; Liang, Guiqing; Kim, Hyungchul; Hoffmann, Peter; Hein, Andreas; Ramage, Paul; D'arcy, Allan; Harlfinger, Stefanie; Renatus, Martin; Ruedisser, Simon; Feldman, David; Elliott, Jason; Sedrani, Richard; Maibaum, Juergen; Adams, Christopher M. [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8088 - 8113]
  • 29
  • [ 878741-84-5 ]
  • (S)-2-(2-((3-(3-amino-2,3-dihydrobenzofuran-5-yl)-5-(2-cyanopropan-2-yl)benzyl)oxy)phenyl)acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 1.3: 16 h / 20 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2.2: 18 h / 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 4.1: potassium acetate; XPhos; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / ethanol / 1 h / 80 °C / Inert atmosphere 5.1: potassium carbonate / water; ethanol / 17 h / 80 °C 6.1: sodium hydroxide / water; tetrahydrofuran; methanol / 16 h / 20 °C
Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2.2: 18 h / 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 4.1: potassium acetate; XPhos; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / ethanol / 1 h / 80 °C / Inert atmosphere 5.1: potassium carbonate / water; ethanol / 17 h / 80 °C 6.1: sodium hydroxide / water; tetrahydrofuran; methanol / 16 h / 20 °C
Reference: [1]Lorthiois, Edwige; Roache, James; Barnes-Seeman, David; Altmann, Eva; Hassiepen, Ulrich; Turner, Gordon; Duvadie, Rohit; Hornak, Viktor; Karki, Rajeshri G.; Schiering, Nikolaus; Weihofen, Wilhelm A.; Perruccio, Francesca; Calhoun, Amy; Fazal, Tanzina; Dedic, Darija; Durand, Corinne; Dussauge, Solene; Fettis, Kamal; Tritsch, Fabien; Dentel, Celine; Druet, Adelaide; Liu, Donglei; Kirman, Louise; Lachal, Julie; Namoto, Kenji; Bevan, Douglas; Mo, Rose; Monnet, Gabriela; Muller, Lionel; Zessis, Richard; Huang, Xueming; Lindsley, Loren; Currie, Treeve; Chiu, Yu-Hsin; Fridrich, Cary; Delgado, Peter; Wang, Shuangxi; Hollis-Symynkywicz, Micah; Berghausen, Joerg; Williams, Eric; Liu, Hong; Liang, Guiqing; Kim, Hyungchul; Hoffmann, Peter; Hein, Andreas; Ramage, Paul; D'arcy, Allan; Harlfinger, Stefanie; Renatus, Martin; Ruedisser, Simon; Feldman, David; Elliott, Jason; Sedrani, Richard; Maibaum, Juergen; Adams, Christopher M. [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8088 - 8113]
[2]Lorthiois, Edwige; Roache, James; Barnes-Seeman, David; Altmann, Eva; Hassiepen, Ulrich; Turner, Gordon; Duvadie, Rohit; Hornak, Viktor; Karki, Rajeshri G.; Schiering, Nikolaus; Weihofen, Wilhelm A.; Perruccio, Francesca; Calhoun, Amy; Fazal, Tanzina; Dedic, Darija; Durand, Corinne; Dussauge, Solene; Fettis, Kamal; Tritsch, Fabien; Dentel, Celine; Druet, Adelaide; Liu, Donglei; Kirman, Louise; Lachal, Julie; Namoto, Kenji; Bevan, Douglas; Mo, Rose; Monnet, Gabriela; Muller, Lionel; Zessis, Richard; Huang, Xueming; Lindsley, Loren; Currie, Treeve; Chiu, Yu-Hsin; Fridrich, Cary; Delgado, Peter; Wang, Shuangxi; Hollis-Symynkywicz, Micah; Berghausen, Joerg; Williams, Eric; Liu, Hong; Liang, Guiqing; Kim, Hyungchul; Hoffmann, Peter; Hein, Andreas; Ramage, Paul; D'arcy, Allan; Harlfinger, Stefanie; Renatus, Martin; Ruedisser, Simon; Feldman, David; Elliott, Jason; Sedrani, Richard; Maibaum, Juergen; Adams, Christopher M. [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8088 - 8113]
  • 30
  • [ 878741-84-5 ]
  • (S)-2-(2-((3-(3-amino-2,3-dihydrobenzofuran-5-yl)-5-(2-cyanopropan-2-yl)benzyl)oxy)phenyl)acetic acid [ No CAS ]
  • (S)-2-(2-((3-(3-amino-2,3-dihydrobenzofuran-5-yl)-5-(1-amino-2-methyl-1-oxopropan-2-yl)benzyl)oxy)phenyl)acetic acid trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 1.3: 16 h / 20 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2.2: 18 h / 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 4.1: potassium acetate; XPhos; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / ethanol / 1 h / 80 °C / Inert atmosphere 5.1: potassium carbonate / water; ethanol / 17 h / 80 °C 6.1: sodium hydroxide / <i>tert</i>-butyl alcohol / 22 h / 80 - 120 °C
Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2.2: 18 h / 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 4.1: potassium acetate; XPhos; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / ethanol / 1 h / 80 °C / Inert atmosphere 5.1: potassium carbonate / water; ethanol / 17 h / 80 °C 6.1: sodium hydroxide / <i>tert</i>-butyl alcohol / 22 h / 80 - 120 °C
Reference: [1]Lorthiois, Edwige; Roache, James; Barnes-Seeman, David; Altmann, Eva; Hassiepen, Ulrich; Turner, Gordon; Duvadie, Rohit; Hornak, Viktor; Karki, Rajeshri G.; Schiering, Nikolaus; Weihofen, Wilhelm A.; Perruccio, Francesca; Calhoun, Amy; Fazal, Tanzina; Dedic, Darija; Durand, Corinne; Dussauge, Solene; Fettis, Kamal; Tritsch, Fabien; Dentel, Celine; Druet, Adelaide; Liu, Donglei; Kirman, Louise; Lachal, Julie; Namoto, Kenji; Bevan, Douglas; Mo, Rose; Monnet, Gabriela; Muller, Lionel; Zessis, Richard; Huang, Xueming; Lindsley, Loren; Currie, Treeve; Chiu, Yu-Hsin; Fridrich, Cary; Delgado, Peter; Wang, Shuangxi; Hollis-Symynkywicz, Micah; Berghausen, Joerg; Williams, Eric; Liu, Hong; Liang, Guiqing; Kim, Hyungchul; Hoffmann, Peter; Hein, Andreas; Ramage, Paul; D'arcy, Allan; Harlfinger, Stefanie; Renatus, Martin; Ruedisser, Simon; Feldman, David; Elliott, Jason; Sedrani, Richard; Maibaum, Juergen; Adams, Christopher M. [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8088 - 8113]
[2]Lorthiois, Edwige; Roache, James; Barnes-Seeman, David; Altmann, Eva; Hassiepen, Ulrich; Turner, Gordon; Duvadie, Rohit; Hornak, Viktor; Karki, Rajeshri G.; Schiering, Nikolaus; Weihofen, Wilhelm A.; Perruccio, Francesca; Calhoun, Amy; Fazal, Tanzina; Dedic, Darija; Durand, Corinne; Dussauge, Solene; Fettis, Kamal; Tritsch, Fabien; Dentel, Celine; Druet, Adelaide; Liu, Donglei; Kirman, Louise; Lachal, Julie; Namoto, Kenji; Bevan, Douglas; Mo, Rose; Monnet, Gabriela; Muller, Lionel; Zessis, Richard; Huang, Xueming; Lindsley, Loren; Currie, Treeve; Chiu, Yu-Hsin; Fridrich, Cary; Delgado, Peter; Wang, Shuangxi; Hollis-Symynkywicz, Micah; Berghausen, Joerg; Williams, Eric; Liu, Hong; Liang, Guiqing; Kim, Hyungchul; Hoffmann, Peter; Hein, Andreas; Ramage, Paul; D'arcy, Allan; Harlfinger, Stefanie; Renatus, Martin; Ruedisser, Simon; Feldman, David; Elliott, Jason; Sedrani, Richard; Maibaum, Juergen; Adams, Christopher M. [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8088 - 8113]
  • 31
  • [ 878741-84-5 ]
  • methyl 2-(2-((3-bromo-5-(2-cyanopropan-2-yl)benzyl)oxy)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 1.3: 16 h / 20 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2.2: 18 h / 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2.2: 18 h / 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
Reference: [1]Lorthiois, Edwige; Roache, James; Barnes-Seeman, David; Altmann, Eva; Hassiepen, Ulrich; Turner, Gordon; Duvadie, Rohit; Hornak, Viktor; Karki, Rajeshri G.; Schiering, Nikolaus; Weihofen, Wilhelm A.; Perruccio, Francesca; Calhoun, Amy; Fazal, Tanzina; Dedic, Darija; Durand, Corinne; Dussauge, Solene; Fettis, Kamal; Tritsch, Fabien; Dentel, Celine; Druet, Adelaide; Liu, Donglei; Kirman, Louise; Lachal, Julie; Namoto, Kenji; Bevan, Douglas; Mo, Rose; Monnet, Gabriela; Muller, Lionel; Zessis, Richard; Huang, Xueming; Lindsley, Loren; Currie, Treeve; Chiu, Yu-Hsin; Fridrich, Cary; Delgado, Peter; Wang, Shuangxi; Hollis-Symynkywicz, Micah; Berghausen, Joerg; Williams, Eric; Liu, Hong; Liang, Guiqing; Kim, Hyungchul; Hoffmann, Peter; Hein, Andreas; Ramage, Paul; D'arcy, Allan; Harlfinger, Stefanie; Renatus, Martin; Ruedisser, Simon; Feldman, David; Elliott, Jason; Sedrani, Richard; Maibaum, Juergen; Adams, Christopher M. [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8088 - 8113]
[2]Lorthiois, Edwige; Roache, James; Barnes-Seeman, David; Altmann, Eva; Hassiepen, Ulrich; Turner, Gordon; Duvadie, Rohit; Hornak, Viktor; Karki, Rajeshri G.; Schiering, Nikolaus; Weihofen, Wilhelm A.; Perruccio, Francesca; Calhoun, Amy; Fazal, Tanzina; Dedic, Darija; Durand, Corinne; Dussauge, Solene; Fettis, Kamal; Tritsch, Fabien; Dentel, Celine; Druet, Adelaide; Liu, Donglei; Kirman, Louise; Lachal, Julie; Namoto, Kenji; Bevan, Douglas; Mo, Rose; Monnet, Gabriela; Muller, Lionel; Zessis, Richard; Huang, Xueming; Lindsley, Loren; Currie, Treeve; Chiu, Yu-Hsin; Fridrich, Cary; Delgado, Peter; Wang, Shuangxi; Hollis-Symynkywicz, Micah; Berghausen, Joerg; Williams, Eric; Liu, Hong; Liang, Guiqing; Kim, Hyungchul; Hoffmann, Peter; Hein, Andreas; Ramage, Paul; D'arcy, Allan; Harlfinger, Stefanie; Renatus, Martin; Ruedisser, Simon; Feldman, David; Elliott, Jason; Sedrani, Richard; Maibaum, Juergen; Adams, Christopher M. [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8088 - 8113]
  • 32
  • [ 878741-84-5 ]
  • C20H22BNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 1.3: 16 h / 20 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2.2: 18 h / 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 4.1: potassium acetate; XPhos; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / ethanol / 1 h / 80 °C / Inert atmosphere
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2.2: 18 h / 20 °C / Inert atmosphere 3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 4.1: potassium acetate; XPhos; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / ethanol / 1 h / 80 °C / Inert atmosphere
Reference: [1]Lorthiois, Edwige; Roache, James; Barnes-Seeman, David; Altmann, Eva; Hassiepen, Ulrich; Turner, Gordon; Duvadie, Rohit; Hornak, Viktor; Karki, Rajeshri G.; Schiering, Nikolaus; Weihofen, Wilhelm A.; Perruccio, Francesca; Calhoun, Amy; Fazal, Tanzina; Dedic, Darija; Durand, Corinne; Dussauge, Solene; Fettis, Kamal; Tritsch, Fabien; Dentel, Celine; Druet, Adelaide; Liu, Donglei; Kirman, Louise; Lachal, Julie; Namoto, Kenji; Bevan, Douglas; Mo, Rose; Monnet, Gabriela; Muller, Lionel; Zessis, Richard; Huang, Xueming; Lindsley, Loren; Currie, Treeve; Chiu, Yu-Hsin; Fridrich, Cary; Delgado, Peter; Wang, Shuangxi; Hollis-Symynkywicz, Micah; Berghausen, Joerg; Williams, Eric; Liu, Hong; Liang, Guiqing; Kim, Hyungchul; Hoffmann, Peter; Hein, Andreas; Ramage, Paul; D'arcy, Allan; Harlfinger, Stefanie; Renatus, Martin; Ruedisser, Simon; Feldman, David; Elliott, Jason; Sedrani, Richard; Maibaum, Juergen; Adams, Christopher M. [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8088 - 8113]
[2]Lorthiois, Edwige; Roache, James; Barnes-Seeman, David; Altmann, Eva; Hassiepen, Ulrich; Turner, Gordon; Duvadie, Rohit; Hornak, Viktor; Karki, Rajeshri G.; Schiering, Nikolaus; Weihofen, Wilhelm A.; Perruccio, Francesca; Calhoun, Amy; Fazal, Tanzina; Dedic, Darija; Durand, Corinne; Dussauge, Solene; Fettis, Kamal; Tritsch, Fabien; Dentel, Celine; Druet, Adelaide; Liu, Donglei; Kirman, Louise; Lachal, Julie; Namoto, Kenji; Bevan, Douglas; Mo, Rose; Monnet, Gabriela; Muller, Lionel; Zessis, Richard; Huang, Xueming; Lindsley, Loren; Currie, Treeve; Chiu, Yu-Hsin; Fridrich, Cary; Delgado, Peter; Wang, Shuangxi; Hollis-Symynkywicz, Micah; Berghausen, Joerg; Williams, Eric; Liu, Hong; Liang, Guiqing; Kim, Hyungchul; Hoffmann, Peter; Hein, Andreas; Ramage, Paul; D'arcy, Allan; Harlfinger, Stefanie; Renatus, Martin; Ruedisser, Simon; Feldman, David; Elliott, Jason; Sedrani, Richard; Maibaum, Juergen; Adams, Christopher M. [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8088 - 8113]
  • 33
  • [ 878741-84-5 ]
  • 2-(3-bromo-5-(hydroxylmethyl)phenyl)-2-methylpropanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 1.3: 16 h / 20 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2.2: 18 h / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 2.2: 18 h / 20 °C / Inert atmosphere
Reference: [1]Lorthiois, Edwige; Roache, James; Barnes-Seeman, David; Altmann, Eva; Hassiepen, Ulrich; Turner, Gordon; Duvadie, Rohit; Hornak, Viktor; Karki, Rajeshri G.; Schiering, Nikolaus; Weihofen, Wilhelm A.; Perruccio, Francesca; Calhoun, Amy; Fazal, Tanzina; Dedic, Darija; Durand, Corinne; Dussauge, Solene; Fettis, Kamal; Tritsch, Fabien; Dentel, Celine; Druet, Adelaide; Liu, Donglei; Kirman, Louise; Lachal, Julie; Namoto, Kenji; Bevan, Douglas; Mo, Rose; Monnet, Gabriela; Muller, Lionel; Zessis, Richard; Huang, Xueming; Lindsley, Loren; Currie, Treeve; Chiu, Yu-Hsin; Fridrich, Cary; Delgado, Peter; Wang, Shuangxi; Hollis-Symynkywicz, Micah; Berghausen, Joerg; Williams, Eric; Liu, Hong; Liang, Guiqing; Kim, Hyungchul; Hoffmann, Peter; Hein, Andreas; Ramage, Paul; D'arcy, Allan; Harlfinger, Stefanie; Renatus, Martin; Ruedisser, Simon; Feldman, David; Elliott, Jason; Sedrani, Richard; Maibaum, Juergen; Adams, Christopher M. [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8088 - 8113]
[2]Lorthiois, Edwige; Roache, James; Barnes-Seeman, David; Altmann, Eva; Hassiepen, Ulrich; Turner, Gordon; Duvadie, Rohit; Hornak, Viktor; Karki, Rajeshri G.; Schiering, Nikolaus; Weihofen, Wilhelm A.; Perruccio, Francesca; Calhoun, Amy; Fazal, Tanzina; Dedic, Darija; Durand, Corinne; Dussauge, Solene; Fettis, Kamal; Tritsch, Fabien; Dentel, Celine; Druet, Adelaide; Liu, Donglei; Kirman, Louise; Lachal, Julie; Namoto, Kenji; Bevan, Douglas; Mo, Rose; Monnet, Gabriela; Muller, Lionel; Zessis, Richard; Huang, Xueming; Lindsley, Loren; Currie, Treeve; Chiu, Yu-Hsin; Fridrich, Cary; Delgado, Peter; Wang, Shuangxi; Hollis-Symynkywicz, Micah; Berghausen, Joerg; Williams, Eric; Liu, Hong; Liang, Guiqing; Kim, Hyungchul; Hoffmann, Peter; Hein, Andreas; Ramage, Paul; D'arcy, Allan; Harlfinger, Stefanie; Renatus, Martin; Ruedisser, Simon; Feldman, David; Elliott, Jason; Sedrani, Richard; Maibaum, Juergen; Adams, Christopher M. [Journal of Medicinal Chemistry, 2020, vol. 63, # 15, p. 8088 - 8113]
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