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[ CAS No. 1184173-73-6 ] {[proInfo.proName]}

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Chemical Structure| 1184173-73-6
Chemical Structure| 1184173-73-6
Structure of 1184173-73-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1184173-73-6 ]

CAS No. :1184173-73-6 MDL No. :N/A
Formula : C37H41N9O3S Boiling Point : -
Linear Structure Formula :- InChI Key :KPQQGHGDBBJGFA-QNGWXLTQSA-N
M.W : 691.85 Pubchem ID :58282870
Synonyms :
SCH900353
Chemical Name :(S)-N-(3-(6-Isopropoxypyridin-3-yl)-1H-indazol-5-yl)-1-(2-(4-(4-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl)-3,6-dihydropyridin-1(2H)-yl)-2-oxoethyl)-3-(methylthio)pyrrolidine-3-carboxamide

Calculated chemistry of [ 1184173-73-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 50
Num. arom. heavy atoms : 26
Fraction Csp3 : 0.35
Num. rotatable bonds : 12
Num. H-bond acceptors : 8.0
Num. H-bond donors : 2.0
Molar Refractivity : 204.93
TPSA : 159.46 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.01
Log Po/w (XLOGP3) : 4.27
Log Po/w (WLOGP) : 4.32
Log Po/w (MLOGP) : 2.76
Log Po/w (SILICOS-IT) : 4.61
Consensus Log Po/w : 3.99

Druglikeness

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

Water Solubility

Log S (ESOL) : -6.41
Solubility : 0.000268 mg/ml ; 0.000000387 mol/l
Class : Poorly soluble
Log S (Ali) : -7.33
Solubility : 0.0000323 mg/ml ; 0.0000000467 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -10.01
Solubility : 0.0000000676 mg/ml ; 0.0000000001 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 5.58

Safety of [ 1184173-73-6 ]

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 [ 1184173-73-6 ]

* 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 [ 1184173-73-6 ]

[ 1184173-73-6 ] Synthesis Path-Downstream   1~22

  • 2
  • [ 1184174-06-8 ]
  • C21H25N5O2S*C2HF3O2 [ No CAS ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine at 20℃; The final coupling of the intermediates proceeded by coupling 17 with 10a to obtain 18 in good yield. After deprotection of the Boc and Trityl groups the final coupling with 5 gave (S)-N-(3-(6-isopropoxypyridin-3-yl)- lH-indazol-5-yl)- 1 -(2-(4-(4-(l -methyl- 1H- 1 ,2,4-triazol-3 -yl)phenyl)-3 ,6-dihydropyridin- 1 (2H)- yl)-2-oxoethyl)-3-(methylthio)pyrrolidine-3 -carboxamide after chromatography. Final purification was carried out by crystallization from methanol/diethylether. This synthetic route has been conducted on a scale that delivered (S)-N-(3-(6-isopropoxypyridin-3-yl)-lH-indazol-5- yl)- 1 -(2-(4-(4-( 1 -methyl- 1H- 1 ,2,4-triazol-3 -yl)phenyl)-3 ,6-dihydropyridin- 1 (2H)-yl)-2- oxoethyl)-3-(methylthio)pyrrolidine-3-carboxamide free base (Compound I).
With N-ethyl-N,N-diisopropylamine at 20℃;
  • 3
  • [ 1184173-73-6 ]
  • (S)-N-(3-(6-isopropoxypyridin-3-yl)-1H-indazol-5-yl)-1-(2-(4-(4-(1-methyl-1H-1,2,4-triazol-3-yl)phenyl)-3,6-dihydropyridin-1(2H)-yl)-2-oxoethyl)-3-(methylthio)pyrrolidine-3-carboxamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In water; isopropyl alcohol at 20℃; for 24h; Preparation of HC1 Hydrate Form 1 Compound I was suspended in aqueous isopropanol mixtures followed by the addition of hydrochloric acid. Mixtures were aged at ambient temperature for at least one day yielding a crystalline salt (HC1 Hydrate Form 1).
With hydrogenchloride In water; isopropyl alcohol at 20℃; Preparation of HC1 Hydrate Form 1 Compound I was suspended in aqueous isopropanol mixtures followed by the addition of hydrochloric acid. Mixtures were aged at ambient temperature for at least one day yielding a crystalline salt (HC1 Hydrate Form 1).
  • 4
  • [ 1184174-04-6 ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 2.1: hydrogenchloride / water 2.2: 1 h / 0 °C 3.1: N-ethyl-N,N-diisopropylamine / 20 °C
Multi-step reaction with 3 steps 1: bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0) 2: hydrogenchloride; triethylamine / dichloromethane / 1 h / 0 °C 3: N-ethyl-N,N-diisopropylamine / 20 °C
Multi-step reaction with 3 steps 1.1: Pd(dppf) 2.1: hydrogenchloride / water 2.2: 1 h / 0 °C 3.1: N-ethyl-N,N-diisopropylamine / 20 °C
Multi-step reaction with 4 steps 1.1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere 2.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C / Inert atmosphere 3.1: triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 3.2: 1 h / 0 °C / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 20 - 50 °C / Inert atmosphere

  • 5
  • tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate [ No CAS ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 2.1: hydrogenchloride / water 2.2: 1 h / 0 °C 3.1: N-ethyl-N,N-diisopropylamine / 20 °C
Multi-step reaction with 3 steps 1: bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0) 2: hydrogenchloride; triethylamine / dichloromethane / 1 h / 0 °C 3: N-ethyl-N,N-diisopropylamine / 20 °C
Multi-step reaction with 3 steps 1.1: Pd(dppf) 2.1: hydrogenchloride / water 2.2: 1 h / 0 °C 3.1: N-ethyl-N,N-diisopropylamine / 20 °C
  • 6
  • [ 1184174-05-7 ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water 1.2: 1 h / 0 °C 2.1: N-ethyl-N,N-diisopropylamine / 20 °C
Multi-step reaction with 2 steps 1: hydrogenchloride; triethylamine / dichloromethane / 1 h / 0 °C 2: N-ethyl-N,N-diisopropylamine / 20 °C
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water 1.2: 1 h / 0 °C 2.1: N-ethyl-N,N-diisopropylamine / 20 °C
Multi-step reaction with 3 steps 1.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 2.2: 1 h / 0 °C / Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 20 - 50 °C / Inert atmosphere

  • 7
  • [ 1184174-06-8 ]
  • C40H39N5O2S*C2HF3O2 [ No CAS ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine at 20℃; (S)-N-(3-(6-isopropoxypyridin-3-yl)- 1H-indazol-5-yl)- 1 -(2-(4-(4-(1 -methyl-1H- 1 ,2,4-triazol-3 -yl)phenyl)-3 , 6-dihydropyridin- 1 (2H)-yl)-2-oxoethyl)-3 -(methylthio)pyrrolidine3-carboxamide free base synthesis is a 19 step process. Compound preparation is divided into three intermediate preparations A, B and C followed by coupling of the intermediates. Allintermediates start with commercially available compounds. Compound 5 is prepared by reaction of the commercially available bromo-4-cyanobenzene with methyl hydrazine under acidic conditions to form the hydrazinoimidate 2 in modest yield. After reaction with formic acid in two steps the bromophenyl-N-methyl triazole intermediate 3 is obtained. The tetrahydropyridine ring is introduced by a Suzuki reaction of the commercially available Bocprotected tetrahydropyridine-boronate to obtain the tricyclic ring system 4. Chloroacetamide 5 is obtained in excellent yield by reaction of the deprotected 4 with chloroacetylchloride. The pyrrolidine core lOa is obtained in good yield in 5 steps starting from commercially available 6. Reaction with thionylchloride gave the thiomethyl olefin 7. Cycloaddition (2+3) gives 8 followed by removal of the benzyl protection group to give 9. L-Tartaric acid resolution of thepyrrolidine core gives the pure (5) enantiomer 9 after filtration from methanol. After protection as the Boc derivative and hydrolysis of the methyl ester, 10 is obtained in overall 50% yield. Compound 17 is obtained from commercially available indazole 11. Bromination at the 3- position of indazole 11 proceeds in excellent yield without chromatography to obtain 12. Suzuki reaction of the bromo compound 12 with 14 gives the nitro indazole 16 after chromatography.Reduction of 16 gives aniline 17 as an oil in quantitative yield without chromatography. The final coupling of the intermediates proceeded by coupling 17 with lOa to obtain 18 in good yield. After deprotection of the Boc and Trityl groups the final coupling with 5 gave (S)-N-(3-(6- isopropoxypyridin-3-yl)- 1H-indazol-5-yl)-1 -(2-(4-(4-(1 -methyl-1H- 1 ,2,4-triazol-3-yl)phenyl)- 3 ,6-dihydropyridin- 1 (2H)-yl)-2-oxoethyl)-3 -(methylthio)pyrrolidine-3 -carboxamide afterchromatography. Final purification is carried out by crystallization from methanol/diethylether.This synthetic route has been conducted on a scale that delivered (S)-N-(3-(6-isopropoxypyridin-3-yl)-1H-indazol-5-yl)- 1 -(2-(4-(4-(1 -methyl-1H- 1 ,2,4-triazol-3-yl)phenyl)-3,6-dihydropyridin-1 (2H)-yl)-2-oxoethyl)-3 -(methylthio)pyrroli dine-3 -carboxamide free base (Compound I).
  • 8
  • [ 1184174-14-8 ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: palladium 10% on activated carbon; hydrogen / toluene; isopropyl alcohol / 24 h / 20 °C 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 20 - 50 °C / Inert atmosphere
  • 9
  • [ 1184174-15-9 ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 20 - 50 °C / Inert atmosphere
  • 10
  • [ 13466-38-1 ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / dimethyl sulfoxide / 2 h / 100 °C / Inert atmosphere 3: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 2 h / 100 °C / Inert atmosphere 4: palladium 10% on activated carbon; hydrogen / toluene; isopropyl alcohol / 24 h / 20 °C 5: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 7: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 20 - 50 °C / Inert atmosphere
  • 11
  • [ 1184296-78-3 ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: Reflux; Inert atmosphere 2.1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,2-dimethoxyethane / 80 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C / Inert atmosphere 4.1: triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere 4.2: 1 h / 0 °C / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 20 - 50 °C / Inert atmosphere
  • 14
  • [ 122684-33-7 ]
  • [ 1184173-73-6 ]
  • 15
  • [ 942190-28-5 ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: trifluoroacetic acid / dichloromethane / 2 h / Inert atmosphere 2: L-Tartaric acid / methanol / 0.33 h / 75 °C / Inert atmosphere; Resolution of racemate 3: triethylamine / dichloromethane / Inert atmosphere 4: lithium hydroxide / water; tetrahydrofuran; methanol / 20 °C / Inert atmosphere 5: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 7: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 20 - 50 °C / Inert atmosphere
  • 16
  • [ 1093063-60-5 ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: L-Tartaric acid / methanol / 0.33 h / 75 °C / Inert atmosphere; Resolution of racemate 2: triethylamine / dichloromethane / Inert atmosphere 3: lithium hydroxide / water; tetrahydrofuran; methanol / 20 °C / Inert atmosphere 4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 5: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 6: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 20 - 50 °C / Inert atmosphere
  • 17
  • [ 1093063-61-6 ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane / Inert atmosphere 2: lithium hydroxide / water; tetrahydrofuran; methanol / 20 °C / Inert atmosphere 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 5: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 20 - 50 °C / Inert atmosphere
  • 18
  • [ 1093063-63-8 ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: lithium hydroxide / water; tetrahydrofuran; methanol / 20 °C / Inert atmosphere 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 20 - 50 °C / Inert atmosphere
  • 19
  • [ 1093063-64-9 ]
  • [ 1184173-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 21 h / 20 - 50 °C / Inert atmosphere
  • 21
  • [ 870521-31-6 ]
  • [ 1184173-73-6 ]
  • 22
  • [ 871839-91-7 ]
  • [ 1184173-73-6 ]
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