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[ CAS No. 1269440-17-6 ] {[proInfo.proName]}

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Chemical Structure| 1269440-17-6
Chemical Structure| 1269440-17-6
Structure of 1269440-17-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1269440-17-6 ]

CAS No. :1269440-17-6 MDL No. :MFCD25976758
Formula : C22H27ClFN7O4S Boiling Point : -
Linear Structure Formula :- InChI Key :CMJCXYNUCSMDBY-ZDUSSCGKSA-N
M.W : 540.01 Pubchem ID :50922675
Synonyms :
LGX818

Calculated chemistry of [ 1269440-17-6 ]

Physicochemical Properties

Num. heavy atoms : 36
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.36
Num. rotatable bonds : 11
Num. H-bond acceptors : 8.0
Num. H-bond donors : 3.0
Molar Refractivity : 135.81
TPSA : 148.51 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.95
Log Po/w (XLOGP3) : 2.7
Log Po/w (WLOGP) : 5.03
Log Po/w (MLOGP) : 1.27
Log Po/w (SILICOS-IT) : 2.1
Consensus Log Po/w : 2.81

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 2.0
Egan : 1.0
Muegge : 0.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -4.51
Solubility : 0.0166 mg/ml ; 0.0000307 mol/l
Class : Moderately soluble
Log S (Ali) : -5.47
Solubility : 0.00182 mg/ml ; 0.00000338 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.58
Solubility : 0.0000143 mg/ml ; 0.0000000265 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.35

Safety of [ 1269440-17-6 ]

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 [ 1269440-17-6 ]

* 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 [ 1269440-17-6 ]

[ 1269440-17-6 ] Synthesis Path-Downstream   1~48

  • 1
  • [ 1269440-76-7 ]
  • [ 124-63-0 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane at 20℃; for 16h; 5 Example 5Methyl N-r(2S)-l-({4-r3-(5-chloro-2-fluoro-3-methanesulfonamidophenyl)-l-(propan-2-yl)- lH-pyrazol-4-yll p yrimidin-2-yl I amino)propan-2-yll carbamate (Compound 9 in table 1)[00214] Methanesulfonyl chloride (0.277 mL, 3.57 mmol) was added to a solution of (S)-methyl l-(4-(3-(3-amino-5-chloro-2-fluorophenyl)-l-isopropyl-lH-pyrazol-4- yl)pyrimidin-2-ylamino)propan-2-ylcarbamate (550 mg, 1.2 mmol) in DCM (30 niL) and pyridine (10 rnL), and the mixture was stirred at rt for 16 h. Aqueous sodium bicarbonate solution was added, and the mixture was extracted with ethyl acetate and washed with brine. The organic phase was dried over sodium sulfate and concentrated. The crude product was purified by silica gel chromatography (60:1 to 40:1 DCM/methanol) to provide the title compound
  • 2
  • [ 1996-30-1 ]
  • [ 1269440-17-6 ]
  • 3
  • [ 89897-29-0 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: tetrahydrofuran; diethyl ether / 0 °C / Reflux 1.2: pH 7 2.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C 2.2: pH 9 - 10 3.1: 12 h / 155 °C 4.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 5.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 6.1: trichlorophosphate / 16 h / 110 °C 7.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 8.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 9.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 10.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 10.2: pH 6 - 6.5 10.3: 0.17 h / 20 °C / pH 7 - 7.5 11.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 11.2: pH 6 - 6.5 11.3: pH 8.5
Multi-step reaction with 11 steps 1.1: tetrahydrofuran; diethyl ether / 0 °C / Reflux 1.2: pH 7 2.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C 2.2: pH 9 - 10 3.1: tert-Butoxybis(dimethylamino)methane / 114 - 120 °C / Inert atmosphere 4.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 5.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 6.1: trichlorophosphate / 16 h / 110 °C 7.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 8.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 9.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 10.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 10.2: pH 6 - 6.5 10.3: 0.17 h / 20 °C / pH 7 - 7.5 11.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 11.2: pH 6 - 6.5 11.3: pH 8.5
Multi-step reaction with 9 steps 1.1: tetrahydrofuran; diethyl ether / 0 °C / Reflux 1.2: pH 7 2.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C 2.2: pH 9 - 10 3.1: 12 h / 155 °C 4.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 5.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 6.1: trichlorophosphate / 16 h / 110 °C 7.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 8.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 9.1: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 9 steps 1.1: tetrahydrofuran; diethyl ether / 0 °C / Reflux 1.2: pH 7 2.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C 2.2: pH 9 - 10 3.1: tert-Butoxybis(dimethylamino)methane / 114 - 120 °C / Inert atmosphere 4.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 5.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 6.1: trichlorophosphate / 16 h / 110 °C 7.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 8.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 9.1: pyridine / dichloromethane / 16 h / 20 °C

  • 4
  • [ 1269232-93-0 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: diphenylphosphoranyl azide; triethylamine / toluene / 2 h / 75 - 84 °C 1.2: 0.25 h / 35 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 16 h / 100 °C 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 5.2: pH 6 - 6.5 5.3: 0.17 h / 20 °C / pH 7 - 7.5 6.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 6.2: pH 6 - 6.5 6.3: pH 8.5
  • 5
  • [ 1269232-94-1 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 16 h / 100 °C 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 4.2: pH 6 - 6.5 4.3: 0.17 h / 20 °C / pH 7 - 7.5 5.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 5.2: pH 6 - 6.5 5.3: pH 8.5
  • 6
  • [ 1269440-69-8 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 3.2: pH 6 - 6.5 3.3: 0.17 h / 20 °C / pH 7 - 7.5 4.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 4.2: pH 6 - 6.5 4.3: pH 8.5
  • 7
  • [ 1269440-77-8 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 2.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 2.2: pH 6 - 6.5 2.3: 0.17 h / 20 °C / pH 7 - 7.5 3.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 3.2: pH 6 - 6.5 3.3: pH 8.5
  • 8
  • [ 1269440-82-5 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium permanganate / water; <i>tert</i>-butyl alcohol / 2.5 h / 40 - 60 °C 1.2: 1 h / 50 °C 1.3: pH 1 2.1: diphenylphosphoranyl azide; triethylamine / toluene / 2 h / 75 - 84 °C 2.2: 0.25 h / 35 °C 3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 16 h / 100 °C 4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 6.2: pH 6 - 6.5 6.3: 0.17 h / 20 °C / pH 7 - 7.5 7.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 7.2: pH 6 - 6.5 7.3: pH 8.5
  • 9
  • [ 1269440-99-4 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (S)-methyl 1-(4-(3-(5-chloro-2-fluoro-3-(N-(methylsulfonyl)methylsulfonamido)phenyl)-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ylamino)propan-2-ylcarbamate With sodium hydroxide In 2-methyltetrahydrofuran; lithium hydroxide monohydrate at 20 - 23℃; for 0.5h; Stage #2: With hydrogenchloride In 2-methyltetrahydrofuran; lithium hydroxide monohydrate Stage #3: With Sodium hydrogenocarbonate In 2-methyltetrahydrofuran; lithium hydroxide monohydrate 6.20 [00235] Step 20. Methyl N-[(2S)-l-({4-[3-(5-chloro-2-fluoro-3- methanesulf onamidophenyl)- 1 -(propan-2-yl)- 1 H-pyrazol-4-yl]pyrimidin-2-yl } amino)propan-2- yl]carbamate. To a flask was charged (S)-methyl l-(4-(3-(5-chloro-2-fluoro-3-(N- (methylsulfonyl)methylsulfonamido)phenyl)-l-isopropyl-lH-pyrazol-4-yl)pyrimidin-2- ylamino)propan-2-ylcarbamate (-3.8 L methylTHF solution, -531.5 g, 0.86 mol). To the solution was added 3N aqueous sodium hydroxide (1782.8 mL, 5.34 mol) at 15-20 0C with stirring. The mixture was vigorously stirred at 20-23 0C over 30 min and the stirring was stopped. The aqueous layer was discarded. 2N HCl (- 410 mL) was added to the organic layer to adjust the pH to 6.0-6.5, then saturated aqueous sodium bicarbonate solution (-300 mL) was added to adjust the pH - 8.5. The aqueous layer was discarded. The organic layer was washed with 15% aqueous sodium chloride solution (2000 mL). The organic layer was concentrated under vacuum (80 torr) at a bath temperature of 45 0C to give a brown solution (780 g). The solution was diluted with 2-methylTHF (3500 mL), and then a suspension of PICA HP 120N activated carbon (90 g, CDH858) in 2-methylTHF (1 L) was added. The resulting black suspension was warmed to 60 0C and held at 60 0C for 16 h. After the 16 h hold the Pd content was 309 ppm. The mixture was cooled to 20 0C and filtered through a pad of celite (prewetted with 2-methylTHF). The reaction flask was rinsed with 2-methylTHF (500 mL). This rinse was then poured thru the filter cake of PICA/celite. To the filtrate was added PL-TMT resin (90 g). The resulting suspension was heated with stirring to 60 0C and held at this temperature for 4 h. After 4h at 60 0C the Pd content was 2.3 ppm. The mixture was cooled to 20 0C and stirred overnight at 20 0C. The mixture was filtered through a pad of celite (prewetted with 2- methylTHF). The filtrate was concentrated under vacuum (100 - 80 torr) at 40 - 45 0C to give an orange oil. This residual oil was dissolved in 3 L of 200 proof ethanol by warming to 78 0C. The resulting clear orange solution was then cooled to 20 0C over 3h, and a precipitate formed. The mixture was then cooled to 0 0C and held 1 h at 0 0C. The mixture was filtered and the filter cake was washed with ethanol ( 300 mL). The solid was dried 14 h at 40 0C to give the title compound; MP: 186 -189 0C.
With sodium hydroxide
  • 10
  • [ 97619-92-6 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: hydrogenchloride / ethanol; water / 0.33 h / Reflux 2.1: tetrahydrofuran; diethyl ether / 0 °C / Reflux 2.2: pH 7 3.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C 3.2: pH 9 - 10 4.1: tert-Butoxybis(dimethylamino)methane / 114 - 120 °C / Inert atmosphere 5.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 6.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 7.1: trichlorophosphate / 16 h / 110 °C 8.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 9.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 10.1: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 10 steps 1.1: hydrogenchloride / ethanol; water / 0.33 h / Reflux 2.1: tetrahydrofuran; diethyl ether / 0 °C / Reflux 2.2: pH 7 3.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C 3.2: pH 9 - 10 4.1: 12 h / 155 °C 5.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 6.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 7.1: trichlorophosphate / 16 h / 110 °C 8.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 9.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 10.1: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 12 steps 1.1: hydrogenchloride / ethanol; water / 0.33 h / Reflux 2.1: tetrahydrofuran; diethyl ether / 0 °C / Reflux 2.2: pH 7 3.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C 3.2: pH 9 - 10 4.1: tert-Butoxybis(dimethylamino)methane / 114 - 120 °C / Inert atmosphere 5.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 6.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 7.1: trichlorophosphate / 16 h / 110 °C 8.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 9.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 11.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 11.2: pH 6 - 6.5 11.3: 0.17 h / 20 °C / pH 7 - 7.5 12.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 12.2: pH 6 - 6.5 12.3: pH 8.5
Multi-step reaction with 12 steps 1.1: hydrogenchloride / ethanol; water / 0.33 h / Reflux 2.1: tetrahydrofuran; diethyl ether / 0 °C / Reflux 2.2: pH 7 3.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C 3.2: pH 9 - 10 4.1: 12 h / 155 °C 5.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 6.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 7.1: trichlorophosphate / 16 h / 110 °C 8.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 9.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 11.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 11.2: pH 6 - 6.5 11.3: 0.17 h / 20 °C / pH 7 - 7.5 12.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 12.2: pH 6 - 6.5 12.3: pH 8.5

  • 11
  • [ 1269440-48-3 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C 1.2: pH 9 - 10 2.1: 12 h / 155 °C 3.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 4.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 5.1: trichlorophosphate / 16 h / 110 °C 6.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 7.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 9.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 9.2: pH 6 - 6.5 9.3: 0.17 h / 20 °C / pH 7 - 7.5 10.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 10.2: pH 6 - 6.5 10.3: pH 8.5
Multi-step reaction with 10 steps 1.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C 1.2: pH 9 - 10 2.1: tert-Butoxybis(dimethylamino)methane / 114 - 120 °C / Inert atmosphere 3.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 4.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 5.1: trichlorophosphate / 16 h / 110 °C 6.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 7.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 9.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 9.2: pH 6 - 6.5 9.3: 0.17 h / 20 °C / pH 7 - 7.5 10.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 10.2: pH 6 - 6.5 10.3: pH 8.5
Multi-step reaction with 8 steps 1.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C 1.2: pH 9 - 10 2.1: 12 h / 155 °C 3.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 4.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 5.1: trichlorophosphate / 16 h / 110 °C 6.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 7.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 8.1: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 8 steps 1.1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water; acetonitrile / 0 - 20 °C 1.2: pH 9 - 10 2.1: tert-Butoxybis(dimethylamino)methane / 114 - 120 °C / Inert atmosphere 3.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 4.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 5.1: trichlorophosphate / 16 h / 110 °C 6.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 7.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 8.1: pyridine / dichloromethane / 16 h / 20 °C

  • 12
  • [ 1269440-49-4 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: tert-Butoxybis(dimethylamino)methane / 114 - 120 °C / Inert atmosphere 2: lithium hydroxide / iso-butanol / 20 h / 110 °C 3: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 4: trichlorophosphate / 16 h / 110 °C 5: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 6: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 7: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 7 steps 1: 12 h / 155 °C 2: lithium hydroxide / iso-butanol / 20 h / 110 °C 3: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 4: trichlorophosphate / 16 h / 110 °C 5: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 6: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 7: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 9 steps 1.1: tert-Butoxybis(dimethylamino)methane / 114 - 120 °C / Inert atmosphere 2.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 3.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 4.1: trichlorophosphate / 16 h / 110 °C 5.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 6.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 8.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 8.2: pH 6 - 6.5 8.3: 0.17 h / 20 °C / pH 7 - 7.5 9.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 9.2: pH 6 - 6.5 9.3: pH 8.5
Multi-step reaction with 9 steps 1.1: 12 h / 155 °C 2.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 3.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 4.1: trichlorophosphate / 16 h / 110 °C 5.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 6.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 8.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 8.2: pH 6 - 6.5 8.3: 0.17 h / 20 °C / pH 7 - 7.5 9.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 9.2: pH 6 - 6.5 9.3: pH 8.5

  • 13
  • [ 1269440-51-8 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: lithium hydroxide / iso-butanol / 20 h / 110 °C 2: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 3: trichlorophosphate / 16 h / 110 °C 4: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 5: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 6: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 8 steps 1.1: lithium hydroxide / iso-butanol / 20 h / 110 °C 2.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 3.1: trichlorophosphate / 16 h / 110 °C 4.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 5.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 7.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 7.2: pH 6 - 6.5 7.3: 0.17 h / 20 °C / pH 7 - 7.5 8.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 8.2: pH 6 - 6.5 8.3: pH 8.5
  • 14
  • [ 1269440-54-1 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 2: trichlorophosphate / 16 h / 110 °C 3: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 4: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 5: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 7 steps 1.1: trifluoroacetic acid; sodium nitrite / 0 - 20 °C 2.1: trichlorophosphate / 16 h / 110 °C 3.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 6.2: pH 6 - 6.5 6.3: 0.17 h / 20 °C / pH 7 - 7.5 7.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 7.2: pH 6 - 6.5 7.3: pH 8.5
  • 15
  • [ 1269440-57-4 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: trichlorophosphate / 16 h / 110 °C 2: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 3: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 4: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 6 steps 1.1: trichlorophosphate / 16 h / 110 °C 2.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 5.2: pH 6 - 6.5 5.3: 0.17 h / 20 °C / pH 7 - 7.5 6.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 6.2: pH 6 - 6.5 6.3: pH 8.5
  • 16
  • [ 1269440-58-5 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 2: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 3: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 5 steps 1.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 4.2: pH 6 - 6.5 4.3: 0.17 h / 20 °C / pH 7 - 7.5 5.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 5.2: pH 6 - 6.5 5.3: pH 8.5
  • 17
  • [ 14568-46-8 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3 h / 20 °C 1.2: 2 h / 80 °C 2.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 20 °C / 760.05 Torr 3.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 5.1: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 7 steps 1.1: methanesulfonyl chloride; triethylamine / dichloromethane / 3 h / 20 °C 1.2: 2 h / 80 °C 2.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 20 °C / 760.05 Torr 3.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 6.2: pH 6 - 6.5 6.3: 0.17 h / 20 °C / pH 7 - 7.5 7.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 7.2: pH 6 - 6.5 7.3: pH 8.5
  • 18
  • [ 1269440-59-6 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 20 °C / 760.05 Torr 2: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 3: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 4: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 6 steps 1.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 20 °C / 760.05 Torr 2.1: triethylamine / 1,4-dioxane; isopropyl alcohol / 48 h / 125 °C 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 5.2: pH 6 - 6.5 5.3: 0.17 h / 20 °C / pH 7 - 7.5 6.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 6.2: pH 6 - 6.5 6.3: pH 8.5
  • 19
  • [ 1229025-89-1 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / 1,4-dioxane; isopropanol / 48 h / 125 °C 2: anhydrous sodium carbonate / tetrakis-(triphenylphosphine)-palladium / ethanol; lithium hydroxide monohydrate; toluene / 16 h / 85 °C 3: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 5 steps 1.1: triethylamine / 1,4-dioxane; isopropanol / 48 h / 125 °C 2.1: anhydrous sodium carbonate / tetrakis-(triphenylphosphine)-palladium / ethanol; lithium hydroxide monohydrate; toluene / 16 h / 80 °C 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 4.2: pH 6 - 6.5 4.3: 0.17 h / 20 °C / pH 7 - 7.5 5.1: sodium hydroxide / 2-methyltetrahydrofuran; lithium hydroxide monohydrate / 0.5 h / 20 - 23 °C 5.2: pH 6 - 6.5 5.3: pH 8.5
Multi-step reaction with 5 steps 1: triethylamine / 1,4-dioxane / 24 h / Reflux 2: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 12 h / Reflux 3: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 4: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 5: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 5 steps 1: triethylamine / 1,4-dioxane / 24 h / Reflux 2: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 12 h / Reflux 3: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 4: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 5: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 6 steps 1: triethylamine / 1,4-dioxane / 24 h / Reflux 2: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 12 h / Reflux 3: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 4: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 5: triethylamine 6: sodium hydroxide
Multi-step reaction with 6 steps 1: triethylamine / 1,4-dioxane / 24 h / Reflux 2: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 12 h / Reflux 3: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 4: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 5: triethylamine 6: sodium hydroxide

  • 20
  • [ 1269440-60-9 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 85 °C 2: pyridine / dichloromethane / 16 h / 20 °C
Multi-step reaction with 4 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 16 h / 80 °C 2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 3.2: pH 6 - 6.5 3.3: 0.17 h / 20 °C / pH 7 - 7.5 4.1: sodium hydroxide / 2-methyltetrahydrofuran; water / 0.5 h / 20 - 23 °C 4.2: pH 6 - 6.5 4.3: pH 8.5
  • 21
  • [ 1269440-78-9 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / 2-methyltetrahydrofuran / -5 - 20 °C 1.2: pH 6 - 6.5 1.3: 0.17 h / 20 °C / pH 7 - 7.5 2.1: sodium hydroxide / 2-methyltetrahydrofuran; lithium hydroxide monohydrate / 0.5 h / 20 - 23 °C 2.2: pH 6 - 6.5 2.3: pH 8.5
Multi-step reaction with 2 steps 1: triethylamine 2: sodium hydroxide
  • 22
  • 3-(3-(benzylamino)-5-chloro-2-fluorophenyl)-1-isopropyl-1H-pyrazole-4-carboxamide [ No CAS ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 2: toluene-4-sulfonic acid; NaNO2; potassium iodide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 3: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 4: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 5: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 5 steps 1: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 2: toluene-4-sulfonic acid; NaNO2; potassium bromide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 3: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 4: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 5: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 6 steps 1: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 2: toluene-4-sulfonic acid; NaNO2; potassium iodide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 3: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 4: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 5: triethylamine 6: sodium hydroxide
Multi-step reaction with 6 steps 1: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 2: toluene-4-sulfonic acid; NaNO2; potassium bromide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 3: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 4: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 5: triethylamine 6: sodium hydroxide

  • 23
  • 3-(3-(benzylamino)-5-chloro-2-fluorophenyl)-1-isopropyl-1H-pyrazol-4-amine [ No CAS ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid; NaNO2; potassium iodide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 2: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 3: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 4: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid; NaNO2; potassium bromide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 2: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 3: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 4: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 5 steps 1: toluene-4-sulfonic acid; NaNO2; potassium iodide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 2: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 3: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 4: triethylamine 5: sodium hydroxide
Multi-step reaction with 5 steps 1: toluene-4-sulfonic acid; NaNO2; potassium bromide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 2: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 3: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 4: triethylamine 5: sodium hydroxide

  • 24
  • N-benzyl-5-chloro-2-fluoro-3-(4-iodo-1-isopropyl-1H-pyrazol-3-yl)aniline [ No CAS ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 2: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 3: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 4 steps 1: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 2: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 3: triethylamine 4: sodium hydroxide
  • 25
  • N-benzyl-5-chloro-2-fluoro-3-(4-bromo-1-isopropyl-1H-pyrazol-3-yl)aniline [ No CAS ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 2: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 3: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 4 steps 1: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 2: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 3: triethylamine 4: sodium hydroxide
  • 26
  • methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-benzylaminophenyl)isopropyl-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate [ No CAS ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 2: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 2: triethylamine 3: sodium hydroxide
  • 27
  • [ 1269440-78-9 ]
  • [ 124-63-0 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
78.3% With triethylamine In dichloromethane at 20℃; for 18h; 4.1 Compound: Encorafenib Method 1: According to the operation of CN201080038197 patent, compound 1 methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-aminophenyl)isopropyl-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate (45g, 0.097mol),Triethylamine (19.6g, 0.194mol), 500ml of dichloromethane, methanesulfonyl chloride (11.1g, 0.097mol) was added dropwise at room temperature, the dropwise addition was completed, and the reaction was continued for 18h,The reaction solution was added with sodium bicarbonate solution to adjust the pH to 7-8, the solution was separated, washed with brine, the organic phase was concentrated to dryness, and purified by column chromatography to obtain 41.0 g of an off-white solid with a yield of 78.3%.
  • 28
  • methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-(4-methoxybenzyl)aminophenyl)isopropyl-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate [ No CAS ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 2: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 2: triethylamine 3: sodium hydroxide
  • 29
  • methyl N-[(2S)-1-({4-[3-(5-chloro-2-fluoro-3-(3,4-dimethoxybenzyl)aminophenyl)isopropyl-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-yl]carbamate [ No CAS ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 2: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 2: triethylamine 3: sodium hydroxide
  • 30
  • methyl (S)-(1-((4-bromopyrimidin-2-yl)amino)propan-2-yl)carbamate [ No CAS ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 12 h / Reflux 2: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 3: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 4: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 4 steps 1: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 12 h / Reflux 2: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 3: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 4: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 5 steps 1: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 12 h / Reflux 2: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 3: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 4: triethylamine 5: sodium hydroxide
Multi-step reaction with 5 steps 1: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 12 h / Reflux 2: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 3: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 4: triethylamine 5: sodium hydroxide

  • 31
  • (S)-methyl (1-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)amino)propan-2-yl)carbamate [ No CAS ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 2: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 3: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 3 steps 1: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 2: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 3: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 4 steps 1: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 2: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 3: triethylamine 4: sodium hydroxide
Multi-step reaction with 4 steps 1: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 2: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 3: triethylamine 4: sodium hydroxide

  • 32
  • [ 1269232-95-2 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: triethylamine / dichloromethane / 4 h / 20 °C 2: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 18 h / Reflux 3: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 4: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 5: toluene-4-sulfonic acid; NaNO2; potassium iodide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 6: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 7: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 8: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 8 steps 1: triethylamine / dichloromethane / 4 h / 20 °C 2: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 18 h / Reflux 3: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 4: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 5: toluene-4-sulfonic acid; NaNO2; potassium bromide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 6: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 7: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 8: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 9 steps 1: triethylamine / dichloromethane / 4 h / 20 °C 2: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 18 h / Reflux 3: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 4: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 5: toluene-4-sulfonic acid; NaNO2; potassium iodide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 6: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 7: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 8: triethylamine 9: sodium hydroxide
Multi-step reaction with 9 steps 1: triethylamine / dichloromethane / 4 h / 20 °C 2: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 18 h / Reflux 3: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 4: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 5: toluene-4-sulfonic acid; NaNO2; potassium bromide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 6: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 7: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 8: triethylamine 9: sodium hydroxide

  • 33
  • C13H10BrClFN [ No CAS ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 18 h / Reflux 2: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 3: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 4: toluene-4-sulfonic acid; NaNO2; potassium iodide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 5: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 6: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 7: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 7 steps 1: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 18 h / Reflux 2: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 3: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 4: toluene-4-sulfonic acid; NaNO2; potassium bromide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 5: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 6: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 7: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 8 steps 1: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 18 h / Reflux 2: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 3: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 4: toluene-4-sulfonic acid; NaNO2; potassium iodide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 5: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 6: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 7: triethylamine 8: sodium hydroxide
Multi-step reaction with 8 steps 1: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 18 h / Reflux 2: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 3: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 4: toluene-4-sulfonic acid; NaNO2; potassium bromide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 5: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 6: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 7: triethylamine 8: sodium hydroxide

  • 34
  • N-benzyl-5-chloro-2-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline [ No CAS ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 2: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 3: toluene-4-sulfonic acid; NaNO2; potassium iodide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 4: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 5: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 6: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 6 steps 1: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 2: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 3: toluene-4-sulfonic acid; NaNO2; potassium bromide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 4: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 5: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 6: triethylamine / dichloromethane / 18 h / 20 °C
Multi-step reaction with 7 steps 1: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 2: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 3: toluene-4-sulfonic acid; NaNO2; potassium iodide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 4: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 5: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 6: triethylamine 7: sodium hydroxide
Multi-step reaction with 7 steps 1: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 2: bromine; sodium hydroxide / ethanol / 2.5 h / 20 - 75 °C 3: toluene-4-sulfonic acid; NaNO2; potassium bromide / lithium hydroxide monohydrate; acetonitrile / 6 h / 20 °C 4: tetrakis-(triphenylphosphine)-palladium; Sodium hydrogenocarbonate / lithium hydroxide monohydrate; toluene; ethanol / 12 h / Reflux 5: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 12 h / 30 - 45 °C / 760.05 Torr 6: triethylamine 7: sodium hydroxide

  • 35
  • [ 2835610-59-6 ]
  • [ 1269440-17-6 ]
YieldReaction ConditionsOperation in experiment
48% With 4,7-dimethoxy-1,10-phenanthroline; copper oxide nanoparticles; iodine; potassium carbonate In (methylsulfinyl)methane at 140℃; for 10h;
  • 36
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With water; potassium hydroxide In ethanol Overall yield = 85percent; Synthesis of target compounds (s)-n-(3-(4-(2-((2-aminopropyl)amino)pyrimidin-4-yl)-1-isopropyl-1H-pyrazol-3-yl)-5-chloro-2-fluorophenyl)methanesulfonamide (16) Encorafenib (1; 0.350 g; 6.49 mmol) was dissolved in ethanol (10 mL), and KOH 6Maqueous solution (10 mL) was added. The mixture was stirred at 80 C for 7 h. The reactionmixture was neutralized with HCl 6M to pH 7 and the organic solvent evaporated underreduced pressure. The obtained precipitate was filtered, and the filtrate was extracted withTHF (3 15 mL). The organic phases and the collected precipitate were combined and purifiedby flash chromatography using DCM/MeOH 9/1+ 0.1% NH3 as the eluent. Compound16 was obtained in 85% yield as a white solid. 1H NMR (CD3OD) : 8.35 (s, 1H), 8.14 (d,J = 5.3 Hz, 1H), 7.51 (dd, J = 6.5, 2.5 Hz, 1H), 7.17 (s, 1H), 6.74 (s, 1H), 4.62-4.58 (m, 1H),3.32 (s, 1H), 3.28 (dd, J = 3.1, 1.5 Hz, 1H), 2.96 (s, 3H), 1.55 (d, J = 6.7 Hz, 6H), 1.15 (s, 3H).13C NMR (CD3OD) : 162.27 (s), 160.51 (s), 157.64 (s), 151.79 (d, J = 245.9 Hz), 143.27 (s),129.61 (s), 128.57 (d, J = 2.7 Hz), 124.44 (d, J = 16.1 Hz), 123.63 (d, J = 12.6 Hz), 119.58 (s),107.41 (s), 54.68 (s), 44.57 (s), 39.27 (s), 21.70 (s), 15.34 (s). MS (ESI): m/z 480/482 [M-H];MS (ESI+): m/z 482/484 [MH+].
  • 37
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 7 h 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 16 h / 20 °C
  • 38
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 7 h 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 16 h / 20 °C
  • 39
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 7 h 2.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 16 h / 20 °C
  • 40
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 7 h 2.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 16 h / 20 °C
  • 41
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 7 h 2.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 16 h / 20 °C
  • 42
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 7 h 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 16 h / 20 °C
  • 43
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 7 h 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 16 h / 20 °C
  • 44
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 7 h 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 16 h / 20 °C
  • 45
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 7 h 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 16 h / 20 °C
  • 46
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 7 h 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 16 h / 20 °C
  • 47
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 7 h 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 16 h / 20 °C
  • 48
  • [ 1269440-17-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide; water / ethanol / 7 h 2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 2.2: 16 h / 20 °C
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