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[ CAS No. 1352999-04-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1352999-04-2
Chemical Structure| 1352999-04-2
Chemical Structure| 1352999-04-2
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Quality Control of [ 1352999-04-2 ]

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Product Details of [ 1352999-04-2 ]

CAS No. :1352999-04-2 MDL No. :MFCD21091404
Formula : C12H24N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CMEHRZGJNHKUAN-UHFFFAOYSA-N
M.W : 228.33 Pubchem ID :19702915
Synonyms :

Calculated chemistry of [ 1352999-04-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.92
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 64.94
TPSA : 64.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.79
Log Po/w (XLOGP3) : 1.62
Log Po/w (WLOGP) : 2.17
Log Po/w (MLOGP) : 1.44
Log Po/w (SILICOS-IT) : 1.41
Consensus Log Po/w : 1.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.95
Solubility : 2.58 mg/ml ; 0.0113 mol/l
Class : Very soluble
Log S (Ali) : -2.58
Solubility : 0.596 mg/ml ; 0.00261 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.54
Solubility : 0.659 mg/ml ; 0.00288 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.45

Safety of [ 1352999-04-2 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1352999-04-2 ]

* 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 [ 1352999-04-2 ]

[ 1352999-04-2 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 3934-20-1 ]
  • [ 1352999-04-2 ]
  • [ 2171003-37-3 ]
YieldReaction ConditionsOperation in experiment
46% With sodium carbonate In butan-1-ol at 100℃; Inert atmosphere; 1.1 Step 1. Preparation of tert-butyl ({ 1 -[(2-chloropyrimidin-4-yl)aminoj cyclohexyl } - methyl)carbamate (1). A mixture of 2,4-dichloropyrimidine (1.01 g, 6.78 mmol), tert-butyl [(1- aminocyclohexyl)methyljcarbamate (1.47 g, 6.46 mmol), and sodium carbonate (2.33 g,22.Ommol) in 1-butanol (20 mL) was heated to 100 °C under argon overnight. The reaction mixture was cooled to ambient temperature and then filtered on a Buchner funnel washing with ethyl acetate. The filtrate was concentrated in vacuo to a very thick yellow oil. The compound was purified by silica gel chromatography using a gradient from 1:4 to 1:1 ethyl acetate:hexanes affording 1.01 g (46% yield) of the desired product as a white solid.MS (ESI+) for C16H25C1N4025 m/z 341.1 (M+H).
  • 2
  • [ 1352999-04-2 ]
  • [ 49845-33-2 ]
  • [ 2171102-17-1 ]
YieldReaction ConditionsOperation in experiment
3.5 g With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 3h; 4.1 Step 1: Synthesis of tert-Butyl ((1-((2-chloro-5-nitropyrimidin-4-yl)amino)cyclohexyl)methyl)carbamate (193) To a solution of 2,4-dichloro-5-nitropyrimidine (192, 3 g, 15.5 mmol), tert-butyl ((1-amrnocyclohexyl)methyl)carbamate (3.5 g, 15.5 mmol) in THF (20 mL) was added followedby NaHCO3 (4.0 g, 47.6 mmol). After stirring at room temperature for 3 hours, the reaction mixture was quenched with water (20 mL) and extracted with EtOAc (20 mL). The organic layer was separated and washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified by column chromatography to afford tert-butyl ((1- ((2-chloro-5-nitropyrimidin-4-yl)amino)cyclohexyl)methyl)carbamate (193, 3.5 g, 9.1 mmol). MS (ESI+): m/z 386 [M + Hjt
  • 3
  • tert-butyl [(1-aminocyclohexyl)methyl]carbamate [ No CAS ]
  • [ 13544-44-0 ]
  • tert-butyl ((1-((2-chloro-5-iodopyrimidin-4-yl)amino)cyclohexyl)methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
28 g With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 12h; To a solution of <strong>[13544-44-0]2,4-dichloro-5-iodopyrimidine</strong> (1, 25 g, 91.2 mmol) and tert-butyl ((1- aminocyclohexyl)methyl)carbamate (2, 20.5 g, 89.9 mmol) in DMF (100 mL) was added K2CO3 (12.4 g, 89.2 mmol). The reaction mixture was stirred at 80 C for 12 h. After cooling to room temperature, the reaction mixture was quenched with water (200 mL) and extracted with EtOAc (200 mL). The organic layer was separated and washed with brine, dried over MgS04, filtered and concentrated in vacuo. The resulting crude product was purified by column chromatography to provide tert-butyl ((l-((2-chloro-5-iodopyrimidin-4- yl)amino)cyclohexyl)methyl)carbamate (3, 28 g, 60.1 mmol). MS (ESI+): m/z 467 [M + H]+.
25 g With potassium carbonate; In N,N-dimethyl acetamide; In Step 1, 20 g of S-23 was reacted with S-24 and potassium carbonate in NJJ- dimethylacetamide at 80 C to provide 25 g of crude S-25.
With potassium carbonate; In N,N-dimethyl acetamide; at 80℃; 1-1 (20 g) was coupled to 1-2 in the presence of K2CO3 in DMAc at 80 oC overnight to afford 1-3. After purification, 25 g of crude 1-3 was obtained.1-3 (15 g) was converted to 1-5 in the presence of 1-4 using (PPh3)2PdCl2, CuI and TEA in THF at 40 oC for 4 hours. After purification, 9.3 g of crude 1-5 was obtained.1-5 (9.3 g) was converted to 1-6 using TBAF in THF at 60 oC for 4 hours.1-6 (5.6 g) was converted to 1-7 using HOAc in THF/H2O at 60 oC for 6 hours. After purification, 3.5 g of 1-7 was obtained.1-7 (1.2 g) was converted to 1-8 using TFA in DCM and stirring at room temperature for 1 hour. After purification, 410 mg of 1-8 was obtained.1-8 (25 mg) was coupled to 1-9 to afford 1-10 using TEA in EtOH and refluxing for 48 hours. After purification, 3.2 mg of 1-10 was obtained. 1-10 was converted to Compound 1 using TFA in DCM. Synthesis
  • 4
  • [ 1352999-04-2 ]
  • [ 1374635-88-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C 2: N-ethyl-N,N-diisopropylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl acetamide 2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 40 °C
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl acetamide / 80 °C 2: bis(triphenylphosphine)palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 4 h / 40 °C
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl acetamide / 80 °C 2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 40 °C

  • 5
  • [ 1352999-04-2 ]
  • [ 1628256-24-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C 2: N-ethyl-N,N-diisopropylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl acetamide 2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 40 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl acetamide / 80 °C 2: bis(triphenylphosphine)palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 4 h / 40 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl acetamide / 80 °C 2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 40 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C

  • 6
  • [ 1352999-04-2 ]
  • [ 1628256-25-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C 2: N-ethyl-N,N-diisopropylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C 4: acetic acid; water / tetrahydrofuran / 60 °C
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl acetamide 2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 40 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C 4: acetic acid / tetrahydrofuran; water / 6 h / 60 °C
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl acetamide / 80 °C 2: bis(triphenylphosphine)palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 4 h / 40 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C 4: acetic acid / tetrahydrofuran; water / 6 h / 60 °C
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl acetamide / 80 °C 2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 40 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C 4: acetic acid / tetrahydrofuran; water / 6 h / 60 °C

  • 7
  • [ 1352999-04-2 ]
  • [ 2170791-56-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 80 °C 2: N-ethyl-N,N-diisopropylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C 4: acetic acid; water / tetrahydrofuran / 60 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl acetamide 2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 40 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C 4: acetic acid / tetrahydrofuran; water / 6 h / 60 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl acetamide / 80 °C 2: bis(triphenylphosphine)palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 4 h / 40 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C 4: acetic acid / tetrahydrofuran; water / 6 h / 60 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl acetamide / 80 °C 2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 40 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C 4: acetic acid / tetrahydrofuran; water / 6 h / 60 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

  • 8
  • [ 1352999-04-2 ]
  • [ 2170747-00-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrogen; platinum on activated charcoal 2.1: hydrogenchloride / water 3.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol / 24 h / 80 - 85 °C 4.1: dmap / dichloromethane / 3 h / 20 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 5.2: 1 h
Multi-step reaction with 5 steps 1.1: hydrogen; platinum on activated charcoal 2.1: hydrogenchloride / water 3.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol 4.1: dmap / dichloromethane / 3 h / 20 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 5.2: 1 h
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile 2.1: 1,2-dichloro-ethane / Reflux 3.1: potassium carbonate / ethanol / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol / 24 h / 80 - 85 °C 5.1: dmap / dichloromethane / 3 h / 20 °C 6.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 6.2: 1 h
Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile 2.1: 1,2-dichloro-ethane / Reflux 3.1: potassium carbonate / ethanol / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol 5.1: dmap / dichloromethane / 3 h / 20 °C 6.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 6.2: 1 h
Multi-step reaction with 8 steps 1: hydrogen; platinum on activated charcoal 2: hydrogenchloride / water 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 60 h 4: dmap / dichloromethane / 3 h / 20 °C 5: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h 6: triethylamine / dichloromethane / 3 h / Inert atmosphere 7: triethylsilane; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; N,N-dimethyl-formamide / 14 h / 45 - 50 °C / Inert atmosphere 8: trifluoroacetic acid / dichloromethane / 20 °C
Multi-step reaction with 9 steps 1: potassium carbonate / acetonitrile 2: 1,2-dichloro-ethane / Reflux 3: potassium carbonate / ethanol / 20 °C 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 60 h 5: dmap / dichloromethane / 3 h / 20 °C 6: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h 7: triethylamine / dichloromethane / 3 h / Inert atmosphere 8: triethylsilane; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; N,N-dimethyl-formamide / 14 h / 45 - 50 °C / Inert atmosphere 9: trifluoroacetic acid / dichloromethane / 20 °C

  • 9
  • [ 1352999-04-2 ]
  • [ 2170747-01-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: potassium carbonate / acetonitrile 2: 1,2-dichloro-ethane / Reflux 3: potassium carbonate / ethanol / 20 °C 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 60 h 5: dmap / dichloromethane / 3 h / 20 °C 6: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h 7: triethylamine / dichloromethane / 3 h / Inert atmosphere 8: triethylsilane; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; N,N-dimethyl-formamide / 14 h / 45 - 50 °C / Inert atmosphere 9: trifluoroacetic acid / dichloromethane / 20 °C 10: Oxone / acetonitrile; water
Multi-step reaction with 6 steps 1.1: hydrogen; platinum on activated charcoal 2.1: hydrogenchloride / water 3.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol / 24 h / 80 - 85 °C 4.1: dmap / dichloromethane / 3 h / 20 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 5.2: 1 h 6.1: Oxone / acetonitrile; water
Multi-step reaction with 6 steps 1.1: hydrogen; platinum on activated charcoal 2.1: hydrogenchloride / water 3.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol 4.1: dmap / dichloromethane / 3 h / 20 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 5.2: 1 h 6.1: Oxone / acetonitrile; water
Multi-step reaction with 7 steps 1.1: potassium carbonate / acetonitrile 2.1: 1,2-dichloro-ethane / Reflux 3.1: potassium carbonate / ethanol / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol / 24 h / 80 - 85 °C 5.1: dmap / dichloromethane / 3 h / 20 °C 6.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 6.2: 1 h 7.1: Oxone / acetonitrile; water
Multi-step reaction with 7 steps 1.1: potassium carbonate / acetonitrile 2.1: 1,2-dichloro-ethane / Reflux 3.1: potassium carbonate / ethanol / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol 5.1: dmap / dichloromethane / 3 h / 20 °C 6.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 6.2: 1 h 7.1: Oxone / acetonitrile; water
Multi-step reaction with 9 steps 1: hydrogen; platinum on activated charcoal 2: hydrogenchloride / water 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 60 h 4: dmap / dichloromethane / 3 h / 20 °C 5: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h 6: triethylamine / dichloromethane / 3 h / Inert atmosphere 7: triethylsilane; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; N,N-dimethyl-formamide / 14 h / 45 - 50 °C / Inert atmosphere 8: trifluoroacetic acid / dichloromethane / 20 °C 9: Oxone / acetonitrile; water

  • 10
  • [ 1352999-04-2 ]
  • [ 1374743-00-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: hydrogen; platinum on activated charcoal 2: hydrogenchloride / water 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 60 h 4: dmap / dichloromethane / 3 h / 20 °C 5: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h 6: triethylamine / dichloromethane / 3 h / Inert atmosphere 7: triethylsilane; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; N,N-dimethyl-formamide / 14 h / 45 - 50 °C / Inert atmosphere 8: trifluoroacetic acid / dichloromethane / 20 °C 9: Oxone / acetonitrile; water 10: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 11 steps 1: potassium carbonate / acetonitrile 2: 1,2-dichloro-ethane / Reflux 3: potassium carbonate / ethanol / 20 °C 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 60 h 5: dmap / dichloromethane / 3 h / 20 °C 6: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h 7: triethylamine / dichloromethane / 3 h / Inert atmosphere 8: triethylsilane; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; N,N-dimethyl-formamide / 14 h / 45 - 50 °C / Inert atmosphere 9: trifluoroacetic acid / dichloromethane / 20 °C 10: Oxone / acetonitrile; water 11: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 7 steps 1.1: hydrogen; platinum on activated charcoal 2.1: hydrogenchloride / water 3.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol / 24 h / 80 - 85 °C 4.1: dmap / dichloromethane / 3 h / 20 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 5.2: 1 h 6.1: Oxone / acetonitrile; water 7.1: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 7 steps 1.1: hydrogen; platinum on activated charcoal 2.1: hydrogenchloride / water 3.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol 4.1: dmap / dichloromethane / 3 h / 20 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 5.2: 1 h 6.1: Oxone / acetonitrile; water 7.1: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 8 steps 1.1: potassium carbonate / acetonitrile 2.1: 1,2-dichloro-ethane / Reflux 3.1: potassium carbonate / ethanol / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol / 24 h / 80 - 85 °C 5.1: dmap / dichloromethane / 3 h / 20 °C 6.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 6.2: 1 h 7.1: Oxone / acetonitrile; water 8.1: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 8 steps 1.1: potassium carbonate / acetonitrile 2.1: 1,2-dichloro-ethane / Reflux 3.1: potassium carbonate / ethanol / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol 5.1: dmap / dichloromethane / 3 h / 20 °C 6.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 6.2: 1 h 7.1: Oxone / acetonitrile; water 8.1: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere

  • 11
  • [ 1352999-04-2 ]
  • [ 1628256-23-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1: hydrogen; platinum on activated charcoal 2: hydrogenchloride / water 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 60 h 4: dmap / dichloromethane / 3 h / 20 °C 5: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h 6: triethylamine / dichloromethane / 3 h / Inert atmosphere 7: triethylsilane; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; N,N-dimethyl-formamide / 14 h / 45 - 50 °C / Inert atmosphere 8: trifluoroacetic acid / dichloromethane / 20 °C 9: Oxone / acetonitrile; water 10: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 11 steps 1: potassium carbonate / acetonitrile 2: 1,2-dichloro-ethane / Reflux 3: potassium carbonate / ethanol / 20 °C 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 60 h 5: dmap / dichloromethane / 3 h / 20 °C 6: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 2 h 7: triethylamine / dichloromethane / 3 h / Inert atmosphere 8: triethylsilane; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; N,N-dimethyl-formamide / 14 h / 45 - 50 °C / Inert atmosphere 9: trifluoroacetic acid / dichloromethane / 20 °C 10: Oxone / acetonitrile; water 11: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 7 steps 1.1: hydrogen; platinum on activated charcoal 2.1: hydrogenchloride / water 3.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol / 24 h / 80 - 85 °C 4.1: dmap / dichloromethane / 3 h / 20 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 5.2: 1 h 6.1: Oxone / acetonitrile; water 7.1: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 7 steps 1.1: hydrogen; platinum on activated charcoal 2.1: hydrogenchloride / water 3.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol 4.1: dmap / dichloromethane / 3 h / 20 °C 5.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 5.2: 1 h 6.1: Oxone / acetonitrile; water 7.1: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 8 steps 1.1: potassium carbonate / acetonitrile 2.1: 1,2-dichloro-ethane / Reflux 3.1: potassium carbonate / ethanol / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol / 24 h / 80 - 85 °C 5.1: dmap / dichloromethane / 3 h / 20 °C 6.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 6.2: 1 h 7.1: Oxone / acetonitrile; water 8.1: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere
Multi-step reaction with 8 steps 1.1: potassium carbonate / acetonitrile 2.1: 1,2-dichloro-ethane / Reflux 3.1: potassium carbonate / ethanol / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / <i>tert</i>-butyl alcohol 5.1: dmap / dichloromethane / 3 h / 20 °C 6.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2.17 h / 20 °C 6.2: 1 h 7.1: Oxone / acetonitrile; water 8.1: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere

  • 12
  • [ 1352999-04-2 ]
  • [ 96-32-2 ]
  • [ 1818414-81-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile 2.4 Step 4 188 g of 24 was subjected to methyl 2-bromoacetate and K2C03 in acetonitrile to afford 25.247 g of crude 25 was obtained.
  • 13
  • [ 924-44-7 ]
  • [ 1352999-04-2 ]
  • [ 2170747-06-3 ]
YieldReaction ConditionsOperation in experiment
With platinum on activated charcoal; hydrogen 2 Scheme 2-4 Scheme 2-4: Starting with compound 17, compounds of the present invention can beprepared. In Step 1 compound 17 is subjected to ethyl 2-oxoacetate in the presence platinum oncarbon and hydrogen gas to afford compound 18. In Step 2 compound 18 is Boc-deprotected with hydrochloric acid. In Step 3 compound 18 is cyclized to afford compound 16 which is used in the schemes above.
  • 14
  • [ 24424-99-5 ]
  • [ 5062-67-9 ]
  • [ 1352999-04-2 ]
YieldReaction ConditionsOperation in experiment
188 g at -70℃; 2.3 Step 3 136 g of the crude 23 from step 2 was converted to 24 with 0.9 eq of Boc2O at -70°C. Thereaction was completed and worked up. After concentration, 188 g of 24 was obtained. The yield was 86%. The H-NIVIR and C-NMR spectra confirmed that the compound was pure.
  • 15
  • [ 1352999-04-2 ]
  • [ 2361994-35-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl acetamide 2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 40 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C 4: acetic acid / tetrahydrofuran; water / 6 h / 60 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6: triethylamine / ethanol / 48 h / Reflux
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl acetamide / 80 °C 2: bis(triphenylphosphine)palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 4 h / 40 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C 4: acetic acid / tetrahydrofuran; water / 6 h / 60 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6: triethylamine / ethanol / 48 h / Reflux
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl acetamide / 80 °C 2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 4 h / 40 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 60 °C 4: acetic acid / tetrahydrofuran; water / 6 h / 60 °C 5: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6: triethylamine / ethanol / 48 h / Reflux
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