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[ CAS No. 199387-77-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 199387-77-4
Chemical Structure| 199387-77-4
Chemical Structure| 199387-77-4
Structure of 199387-77-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 199387-77-4 ]

CAS No. :199387-77-4 MDL No. :MFCD06213013
Formula : C11H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :SNMYVOUKVPUKIJ-UHFFFAOYSA-N
M.W : 173.21 Pubchem ID :11816142
Synonyms :

Calculated chemistry of [ 199387-77-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.09
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 53.64
TPSA : 46.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 1.89
Log Po/w (WLOGP) : 1.85
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 1.85

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.61
Solubility : 0.427 mg/ml ; 0.00247 mol/l
Class : Soluble
Log S (Ali) : -2.48
Solubility : 0.569 mg/ml ; 0.00328 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.54
Solubility : 0.0501 mg/ml ; 0.000289 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 199387-77-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P403+P233-P405-P501 UN#:3259
Hazard Statements:H302-H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 199387-77-4 ]

* 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 [ 199387-77-4 ]

[ 199387-77-4 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 177736-15-1 ]
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  • 2
  • [ 67886-70-8 ]
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  • 3
  • [ 177736-16-2 ]
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  • 4
  • [ 52927-22-7 ]
  • [ 199387-77-4 ]
YieldReaction ConditionsOperation in experiment
100% With ammonia; hydrogen;nickel; In methanol; water; 6-Hydroxy-naphthalene-2-carbonitrile was hydrogenated in the presence of Raney Nickel in methanol and aqueous ammonia. The solution was concentrated under reduced pressure to a semi-solid, which was partitioned between ethyl acetate, and water (50 mL each), separated, washed with water (50 mL), brine (50 mL), dried with magnesium sulfate, filtered and concentrated under reduced pressure to a white solid (6-aminomethyl-naphthalen-2-ol, 1.05 g, quantitative).
  • 6
  • [ 52489-39-1 ]
  • [ 199387-77-4 ]
  • [ 479630-69-8 ]
YieldReaction ConditionsOperation in experiment
78% With triethylamine; In tetrahydrofuran; hexane; Step 2: 2-Butyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-amide. 2-Butyl-benzofuran-3-carbonyl chloride (1.54 g, 6.5 mmol), prepared in step 2 of Example 3, in 45 mL of anhydrous THF was added under nitrogen dropwise over 2 h to a solution of 6-aminomethyl-naphthalen-2-ol (1.13 g, 6.5 mmol), prepared in the previous step, and triethylamine (906 μL, 6.5 mmol) in 150 mL of anhydrous THF at room temperature. After the addition the reaction was stirred at room temperature for 20 h (overnight). The solid was removed by filtration and the filtrate concentrated under reduced pressure to give 2.50 g of a brown oil. Purification of the oil on a 90 g KP-SIL 60 Δ Biotage column using 3:1 hexane:ethyl acetate as the eluent gave 2-butyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-amide (1.88 g, 78%) as a white solid, mp 155-156 C. Elemental Analysis for C24H23NO3 Calc'd: C, 77.19; H, 6.21; N, 3.75 Found: C, 76.99; H, 6.07; N, 3.76
  • 7
  • [ 199387-77-4 ]
  • [ 175137-15-2 ]
  • [ 479630-80-3 ]
YieldReaction ConditionsOperation in experiment
25% In pyridine; dichloromethane; ethyl acetate; Step 1: 1-Phenyl-5-propyl-1H-pyrazole-4-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-amide. 1-Phenyl-5-propyl-1H-pyrazole-4-carbonyl chloride (2.0 g, 8.0 mmol) in 20 mL of methylene chloride was added under nitrogen at room temperature to a suspension of 6-aminomethyl-naphthalen-2-ol (1.63 g, 9.42 mmol), prepared in step 1 of Example 8, in 75 mL of anhydrous pyridine. After the addition the reaction was stirred at room temperature for 17 h (overnight). The reaction was partitioned between methylene chloride and 1 N HCl. The organic layer was separated and the aqueous layer extracted multiple times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give 1.9 g of a brown solid. Recrystallization of the solid one time from ethyl acetate and one time from isopropyl alcohol gave 1-phenyl-5-propyl-1H-pyrazole-4-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-amide (767 mg, 25%) as a tan solid, mp 189-190 C. Elemental Analysis for C24H23N3O2 Calc'd: C, 74.78; H, 6.01; N, 10.90 Found: C, 73.64; H, 5.78; N, 10.77
  • 8
  • [ 199387-77-4 ]
  • [ 479631-04-4 ]
YieldReaction ConditionsOperation in experiment
32% With hydrogenchloride; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; 2-methyl-1-benzofuran-3-carboxylic acid; Step 3: 2-Methyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-amide. 2-Methyl-benzofuran-3-carbonyl chloride, prepared in the previous step, in 50 mL of anhydrous THF was added under nitrogen dropwise over 1.5 h to a solution of 6-aminomethyl-naphthalen-2-ol (1.00 g, 5.79 mmol), prepared in step 1 of Example 8, and triethylamine (811 μL, 5.82 mmol) in 300 mL of anhydrous THF at room temperature. After the addition the reaction was stirred at room temperature for 19 h (overnight). The solvent was removed under reduced pressure. The dark brown residue was partitioned between 400 mL of 20% MeOH in methylene chloride and 1 N HCl. After separating the organic layer, the aqueous layer was extracted three times with 20% MeOH in methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give 1.59 g of a brown solid. The solid was taken up in 50 mL of boiling ethyl acetate, filtered, concentrated to a volume of 25 mL and diluted with 75 mL of hexane. The solid formed was collected by filtration and dried under reduced pressure to give 2-methyl-benzofuran-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-amide (606 mg, 32%) as a brown solid, mp 195-198 C. Elemental Analysis for C21H17NO3 Calc'd: C, 76.12; H, 5.17; N, 4.23 Found: C, 74.62; H, 4.95; N, 3.84
  • 9
  • [ 175276-63-8 ]
  • [ 199387-77-4 ]
  • [ 479630-74-5 ]
YieldReaction ConditionsOperation in experiment
45% In pyridine; dichloromethane; Step 1: 5-(4-Chloro-phenyl)-2-methyl-furan-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-amide. 5-(4-Chloro-phenyl)-2-methyl-furan-3-carbonyl chloride (737 mg, 2.89 mmol) in 25 mL of methylene chloride was added under nitrogen dropwise over 30 minutes to a suspension of 6-aminomethyl-naphthalen-2-ol (500 mg, 2.89 mmol), prepared in step 1 of Example 8, in 25 mL of anhydrous pyridine at ice bath temperature. After the addition the ice bath was removed and the reaction stirred at room temperature overnight. The reaction was partitioned between methylene chloride and 1 N HCl. The organic layer was separated and the aqueous layer was extracted with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give 1.04 g of a brown solid. Purification of the solid on 500 g of silica gel (230-400 mesh) using 10% ethyl acetate-methylene chloride as the eluent gave 5-(4-chloro-phenyl)-2-methyl-furan-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-amide (507 mg, 45%) as a tan solid, mp 202-204 C. Elemental Analysis for C23H18ClNO3 Calc'd: C, 70.50; H, 4.63; N, 3.57 Found: C, 69.25; H, 4.67; N, 3.49
  • 10
  • [ 861448-89-7 ]
  • [ 199387-77-4 ]
  • [ 862540-79-2 ]
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