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[ CAS No. 1032350-13-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1032350-13-2
Chemical Structure| 1032350-13-2
Structure of 1032350-13-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1032350-13-2 ]

CAS No. :1032350-13-2 MDL No. :MFCD14584463
Formula : C25H23Cl2N5O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 480.39 Pubchem ID :-
Synonyms :
MK-2206 (2HCl);MK-2206 (hydrochloride);MK-2206 dihydrochloride

Calculated chemistry of [ 1032350-13-2 ]

Physicochemical Properties

Num. heavy atoms : 33
Num. arom. heavy atoms : 25
Fraction Csp3 : 0.16
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 135.78
TPSA : 89.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 4.59
Log Po/w (WLOGP) : 5.74
Log Po/w (MLOGP) : 4.46
Log Po/w (SILICOS-IT) : 4.38
Consensus Log Po/w : 3.83

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.07
Solubility : 0.000406 mg/ml ; 0.000000846 mol/l
Class : Poorly soluble
Log S (Ali) : -6.18
Solubility : 0.000314 mg/ml ; 0.000000654 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.61
Solubility : 0.00000117 mg/ml ; 0.0000000024 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.27

Safety of [ 1032350-13-2 ]

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 [ 1032350-13-2 ]

* 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 [ 1032350-13-2 ]

[ 1032350-13-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1032350-03-0 ]
  • [ 1032350-13-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: tert-butyl {1-[4-(3-oxo-9-phenyl-2,3-dihydro[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)phenyl]cyclobutyl}carbamate With hydrogenchloride In ethanol; water at 50℃; for 3h; Stage #2: With acetyl chloride In ethanol at 0 - 20℃; for 1.5h; 2 8-[4-(l -Aminocyclobutyl)phenyl]-9-phenyl[ 1 ,2,4]triazolo[3,4- J- 1 ,6- naphthyridin-3(2H)-one (MK-2206) A solution of aqueous concentrated HC1 (12.1 M, 1.64 mL) in ethanol (2.0 mL) was added dropwise over 30 min to a stirred slurry of 1-10 (500 mg, 0.985 mol) in ethanol (1.7 mL) and water (0.2 mL) at 50°C. After 3 hours following acid addition, the mixture was seeded and aged overnight at 50°C, cooled to room temperature and filtered. Acetyl chloride (0.5 g, 7 mmol) was added over 1 h to ethanol (2 mL) at 0°C. The solution was then cooled to room temperature and aged for 30 minutes. The filter cake was washed with this solution (1 mL x 2), then with ethyl acetate (4 mL x 2) and dried, finally in a vacuum oven at 75.0°C with nitrogen sweep (50 torr) to afford MK-2206 as the bis-HCl salt. A mono-HCl version of MK-2206 was also produced via dissolution in water.After 6 hours, the aqueous slurry turns light yellow and is filtered. Silver chloride titration of this solid reveals the presence of one equivalent of chloride.
  • 2
  • [ 893423-62-6 ]
  • MK-2206 [ No CAS ]
  • 3
  • [ 338452-92-9 ]
  • MK-2206 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium hydroxide / isopropyl alcohol / 1 h / 24 °C 2.1: hydrogenchloride / isopropyl alcohol / 16 h / 66 - 70 °C / Cooling 3.1: hydrogenchloride / water; ethanol / 3 h / 50 °C 3.2: 1.5 h / 0 - 20 °C
  • 4
  • [ 1032350-13-2 ]
  • [ 192055-73-5 ]
  • [ 2467989-96-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: MK-2206; Boc-GFLG-OH With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at -5℃; for 0.5h; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at -5 - 20℃; 1 Product 1-95 Boc-GFLG-OH (7.72 mmol), MK-2206.2HCl (2.97 g, 6.18 mmol, referred to as MK2), HBTU (3.52 g, 9.27 mmol) and HOBT (1.25 g, 9.27 mmol) were added in a 250 mL round-bottomed flask and then dissolved with DMF (90 mL), and the mixed solution was stirred at -5° C. for 30 minutes. Then DIEA (6.6 mL, 27.81 mmol) was added dropwise, and then the mixed solution reacted at a low temperature for 2 h; after that, the reaction device was placed at room temperature and the reaction solution was stirred overnight to react. At the end of the reaction, the reaction solution was transferred to a 1000 mL separatory funnel, saturated sodium bicarbonate solution (200 mL) was then added, the obtained solution was extracted three times with ethyl acetate (200 mL×3), and the obtained organic phases were combined and then washed with saturated sodium chloride solution three times (100 mL×3); the organic phase was dewatered, evaporated to dryness under reduced pressure, and then dried in a vacuum box, thus obtaining 8.1 g of the product, with a yield of 148.6%, for next reaction.
Stage #1: MK-2206; Boc-GFLG-OH With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at -5℃; for 0.5h; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at -5 - 20℃; 1 Product 1-95 Boc-GFLG-OH (7.72 mmol), MK-2206.2HCl (2.97 g, 6.18 mmol, referred to as MK2), HBTU (3.52 g, 9.27 mmol) and HOBT (1.25 g, 9.27 mmol) were added in a 250 mL round-bottomed flask and then dissolved with DMF (90 mL), and the mixed solution was stirred at -5° C. for 30 minutes. Then DIEA (6.6 mL, 27.81 mmol) was added dropwise, and then the mixed solution reacted at a low temperature for 2 h; after that, the reaction device was placed at room temperature and the reaction solution was stirred overnight to react. At the end of the reaction, the reaction solution was transferred to a 1000 mL separatory funnel, saturated sodium bicarbonate solution (200 mL) was then added, the obtained solution was extracted three times with ethyl acetate (200 mL×3), and the obtained organic phases were combined and then washed with saturated sodium chloride solution three times (100 mL×3); the organic phase was dewatered, evaporated to dryness under reduced pressure, and then dried in a vacuum box, thus obtaining 8.1 g of the product, with a yield of 148.6%, for next reaction.
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[ 1032350-13-2 ]

Chemical Structure| 1032349-77-1

A1466904[ 1032349-77-1 ]

8-(4-(1-Aminocyclobutyl)phenyl)-9-phenyl-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-3(2H)-one hydrochloride

Reason: Free-salt