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Chemistry
Heterocyclic Building Blocks
Isoxazoles
3,5-Dichlorobenzo[d]isoxazole
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Isoxazoles
Benzisoxazoles Chlorides

[ CAS No. 16263-53-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
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3d Animation Molecule Structure of 16263-53-9
Chemical Structure| 16263-53-9
Chemical Structure| 16263-53-9
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Quality Control of [ 16263-53-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
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Product Details of [ 16263-53-9 ]

CAS No. :16263-53-9 MDL No. :MFCD12756777
Formula : C7H3Cl2NO Boiling Point : -
Linear Structure Formula :- InChI Key :PJMDBZXSQGQSDQ-UHFFFAOYSA-N
M.W : 188.01 Pubchem ID :13568448
Synonyms :

Calculated chemistry of [ 16263-53-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.03
TPSA : 26.03 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) : -5.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.27
Log Po/w (XLOGP3) : 3.3
Log Po/w (WLOGP) : 3.13
Log Po/w (MLOGP) : 2.58
Log Po/w (SILICOS-IT) : 3.18
Consensus Log Po/w : 2.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.69
Solubility : 0.0384 mg/ml ; 0.000204 mol/l
Class : Soluble
Log S (Ali) : -3.52
Solubility : 0.0565 mg/ml ; 0.0003 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.15
Solubility : 0.0134 mg/ml ; 0.0000711 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.5

Safety of [ 16263-53-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16263-53-9 ]

* 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 [ 16263-53-9 ]

[ 16263-53-9 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 110-91-8 ]
  • [ 16263-53-9 ]
  • [ 16302-70-8 ]
Reference： [1]Chemische Berichte,1967,vol. 100,p. 3326 - 3330
  • 2
  • [ 16263-53-9 ]
  • [ 141-52-6 ]
  • [ 16263-62-0 ]
Reference： [1]Chemische Berichte,1967,vol. 100,p. 3326 - 3330
  • 3
  • [ 16263-53-9 ]
  • [ 139-02-6 ]
  • [ 16263-61-9 ]
Reference： [1]Chemische Berichte,1967,vol. 100,p. 3326 - 3330
  • 4
  • [ 16263-53-9 ]
  • 3-azido-5-chloro-benzo[<i>d</i>]isoxazole [ No CAS ]
Reference： [1]Chemische Berichte,1967,vol. 100,p. 3326 - 3330
  • 5
  • [ 16263-53-9 ]
  • [ 24603-63-2 ]
Reference： [1]Chemische Berichte,1967,vol. 100,p. 3326 - 3330
  • 6
  • [ 24603-63-2 ]
  • [ 16263-53-9 ]
YieldReaction ConditionsOperation in experiment
92% With pyridine; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; trichlorophosphate; EXAMPLE 16 3,5-Dichloro-1,2-benzisoxazole To a suspension of 5-chloro-3-hydroxy-1,2-benzisoxazole (100 g) in phosphorus oxychloride (80 ml) was added pyridine (48 ml) dropwise over 1 hours with stirring at room temperature, and the mixture was then refluxed for 5 hours. The reaction mixture was added to ice water (500 ml) and extracted with ethyl acetate and the combined extracts were dried over anhydrous magnesium sulphate. The solvent was evaporated under reduced pressure and the title compound (102 g, 92%) was obtained by recrystallizng the residue from petroleum ether as a colorless needle. Melting point: 43-44 C.; IR spectrum(KBr)numax cm-1: 1468, 1419, 1285; NMR spectrum(CDCl3)deltappm: 7.59(2H,d,J=1.5 Hz), 7.70(1H,brs).
Reference： [1]Patent: US5965591,1999,A
[2]Chemische Berichte,1967,vol. 100,p. 3326 - 3330
  • 7
  • [ 110-85-0 ]
  • [ 16263-53-9 ]
  • [ 99748-43-3 ]
Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 359 - 369
  • 8
  • [ 24603-63-2 ]
  • [ 16263-53-9 ]
Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 359 - 369
  • 10
  • [ 37551-43-2 ]
  • [ 16263-53-9 ]
Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 359 - 369
  • 11
  • [ 16263-53-9 ]
  • [ 99748-50-2 ]
Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 359 - 369
  • 12
  • [ 16263-53-9 ]
  • [ 99748-49-9 ]
Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 359 - 369
  • 13
  • [ 4068-78-4 ]
  • [ 16263-53-9 ]
Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 359 - 369
  • 14
  • [ 16263-53-9 ]
  • [ 178747-64-3 ]
YieldReaction ConditionsOperation in experiment
62% (a) 3-(2-(N-t-Butoxycarbonylamino)ethylthio)-5-chloro-1,2-benzisoxazole. The title compound (0.63 g, 62%) was obtained from <strong>[16263-53-9]3,5-dichloro-1,2-benzisoxazole</strong> (0.53 g) by similar reactions and treatments as in example 26(b). Melting point: 95-96 C.; IR spectrum(KBr)numax cm-1: 3283, 1687, 1523; NMR spectrum(CDCl3)deltappm: 1.44(9H,s), 3.42(2H,t,J=6.3 Hz), 3.58(2H,q,J=6.3 Hz), 4.98(1H,brs), 7.47(1H,d,J=8.8 Hz), 7.52(1H,dd,J=8.8 Hz,J=1.5 Hz), 7.57(1H,d,J=1.5 Hz).
Reference： [1]Patent: US5965591,1999,A
  • 15
  • [ 16263-53-9 ]
  • [ 124-68-5 ]
  • · 3-(2-Amino-2-methylpropoxy)-5-chloro-1,2-benzoisoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; water; ethyl acetate; (1) To a suspension of 0.43 g of 60% (w/w) sodium hydride in 15 ml of tetrahydrofuran is added a solution of 0.80 g of 2-amino-2-methyl-1-propanol in 20 ml of tetrahydrofuran at 20-25 C., and they are refluxed for two hours. To the reaction mixture is added a solution of 2.36 g of <strong>[16263-53-9]3,5-dichloro-1,2-benzoisoxazole</strong> in 20 ml of tetrahydrofuran under reflux, and they are refluxed for a further one hour. After cooling, the solvent is removed by distillation under reduced pressure, and ethyl acetate and water are added to the residue obtained, and after shaking, the organic layer is separated. The separated organic layer is washed with a saturated saline solution, dried over anhydrous magnesium sulfate and then purified by a column chromatography [eluant:chloroform:methanol=20:1], to obtain 1.59 g of oily 3-(2-amino-2-methylpropoxy)-5-chloro-1,2-benzoisoxazole.
Reference： [1]Patent: US5578627,1996,A
  • 16
  • [ 16263-53-9 ]
  • 1,1-dimethylethyl 4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate [ No CAS ]
  • 3-[(3-tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methoxy]-5-chloro-1,2-benzoisoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In tetrahydrofuran; water; ethyl acetate; REFERENCE EXAMPLE 37 A solution of 6.94 g of 3-tert-butoxycarbonyl-4-hydroxymethyl-2,2-dimethyloxazolidine in 28 ml of tetrahydrofuran is added to a solution of 6.02 g of potassium tert-butoxide in 28 ml of tetrahydrofuran at 10-15 C., and they are subjected to reaction at the same temperature for two hours. Subsequently, this reaction mixture is added under reflux to a solution of 5.64 g of <strong>[16263-53-9]3,5-dichloro-1,2-benzoisoxazole</strong> in 28 ml of tetrahydrofuran and they are refluxed for a further one hour. The reaction mixture is cooled and thereafter the solvent is removed by distillation under reduced pressure, after which ethyl acetate and water are added to the residue obtained, and after shaking, the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The crystals obtained are recrystallized from n-hexane to obtain 8.41 g of colorless, crystalline 3-[(3-tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methoxy]-5-chloro-1,2-benzoisoxazole having a melting point of 117-118 C. IR (KBr)cm-1: 2981, 1538, 1462, 1393, 1368, 1177, 830
Reference： [1]Patent: US5578627,1996,A
  • 17
  • (R)-3-methylthio-2-tritylamino-1-propanol [ No CAS ]
  • [ 16263-53-9 ]
  • (R)-5-chloro-3-(3-methylthio-2-tritylaminopropoxy)-1,2-benzoisoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; ethyl acetate; N,N-dimethyl-formamide; EXAMPLE 137 To a suspension of 0.44 g of 60% (w/w) sodium hydride in 6 ml of N,N-dimethylformamide is dropwise added 15 ml of an N,N-dimethylformamide solution of 4.0 g of (R)-3-methylthio-2-tritylamino-1-propanol over 15 minutes with ice-cooling, and the temperature is gradually elevated to 80 C., after which this is added to a solution of 2.07 g of <strong>[16263-53-9]3,5-dichloro-1,2-benzoisoxazole</strong> in 10 ml of N,N-dimethylformamide. They are subjected to reaction at the same temperature for one hour. After cooling, water and ethyl acetate are added and shaken, and the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The residue obtained is purified by a column chromatography [eluant:n-hexane:ethyl acetate=20:1], to obtain 4.4 g of oily (R)-5-chloro-3-(3-methylthio-2-tritylaminopropoxy)-1,2-benzoisoxazole. IR (KBr) cm-1: 3448, 3057, 2921, 1610, 1539, 1486, 1475, 1439, 1358, 1283, 1258, 1028, 810, 708
Reference： [1]Patent: US5578627,1996,A
  • 18
  • 2-(trityl-amino)-3-(1-trityl-1H-imidazol-4-yl)-propan-1-ol [ No CAS ]
  • [ 16263-53-9 ]
  • 5-chloro-3-[2-tritylamino-3-(1-trityl-4-imidazolyl)propoxy]-1,2-benzoisoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; ethyl acetate; N,N-dimethyl-formamide; EXAMPLE 142 A solution of 2.0 g of 2-tritylamino-3-(1-trityl-4-imidazolyl)-1-propanol in 10 ml of N,N-dimethylformamide is dropwise added to a suspension of 0.14 g of 60% (w/w) sodium hydride in 15 ml of N,N-dimethylformamide at room temperature over 15 minutes, and the temperature is then elevated gradually to 80 C., after which this is added to a solution of 0.6 g of <strong>[16263-53-9]3,5-dichloro-1,2-benzoisoxazole</strong> in 10 ml of N,N-dimethylformamide. They are subjected to reaction at the same temperature for six hours. After cooling, water and ethyl acetate are added and shaken, and the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The residue obtained is purified by a column chromatography [eluant:n-hexane:ethyl acetate=3:1], to obtain 1.12 g of colorless, crystalline 5-chloro-3-[2-tritylamino-3-(1-trityl-4-imidazolyl)propoxy]-1,2-benzoisoxazole having a melting point of 113.4-114.7 C. IR (KBr) cm-1: 3445, 3057, 2967, 1596, 1538, 1490, 1474, 1446, 1364, 1310, 1155, 747, 702
Reference： [1]Patent: US5578627,1996,A
  • 19
  • [ 106-52-5 ]
  • [ 16263-53-9 ]
  • [ 138731-29-0 ]
YieldReaction ConditionsOperation in experiment
With sodium chloride; In N-methyl-acetamide; ice-water; ethyl acetate; mineral oil; EXAMPLE 11 5-Chloro-3-(1-methyl-4-piperidyloxy)-1,2-benzisoxazole A solution of 1.53 g (13.3 mmole) of 4-hydroxy-1-methylpiperidine in 25 ml of dimethylformamide was cooled to 5 C. in an atmosphere of nitrogen. 0.58 g (13.3 mmole) of sodium hydride (as a 55% w/w dispersion in mineral oil) was added to the solution, and then the solution was stirred at room temperature for 30 minutes. The reaction mixture was cooled to 5 C., and then 2.50 g (13.3 mmole) of <strong>[16263-53-9]3,5-dichloro-1,2-benzisoxazole</strong> were added to it; the resulting mixture was then stirred at 5 C. for 30 minutes and then at room temperature for 1 hour. At the end of this time, the mixture was poured into 50 ml of ice-water and then extracted twice, each time with 50 ml of ethyl acetate. The ethyl acetate layer was separated and washed with 100 ml of a 10% w/v aqueous solution of sodium chloride; it was then dried over anhydrous magnesium sulfate, and the drying agent was removed by filtration. The solvent was removed from the filtrate by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel using ethyl acetate as the eluent to afford 2.38 g (yield 67.00%) of the title compound as a colorless powder, melting at 55-56 C. Infrared absorption spectrum (CHCl3) cm-1: 1535, 1470, 1440, 1360, 1310. Nuclear magnetic resonance spectrum (CDCl3) delta ppm: 1.73-3.00 (8H, multiplet); 2.32 (3H, singlet); 4.92 (1H, doubled doublet of doublets, J=13.5, 9.0 & 4.5 Hz); 7.30-7.76 (3H, multiplet).
Reference： [1]Patent: US5643923,1997,A
  • 20
  • [ 16263-53-9 ]
  • rac-(1R*,6S*)-3,8-diazabicyclo[4.2.0]octan-8-yl(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride [ No CAS ]
  • rac-((1R*,6S*)-3-(5-chlorobenzo[d]isoxazol-3-yl)-3,8-diazabicyclo[4.2.0]octan-8-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; at 110.0℃; The title compound is prepared by reacting rac-(1 R*,6S*)-3,8-diazabicyclo[4.2.0]octan-8-yl(5- methyl-2-(2H-1 ,2,3-triazol-2-yl)phenyl)methanone hydrochloride (C.2) with 3,5- dichlorobenzo[d]isoxazole (commercially available) following General Method B. LC-MS (conditions B): tR = 0.88 min, [M + 1]+ = 449.09.General Method B Nucleophilic substitutionTo a solution of 1 mmol of secondary amine 1 , 4, 6 or 14 (Schemes 1 + 2 +3 + 4) in pyridine (5.5 mL) are successively added DBU (2.5 mmol for the free amine; 3.5 mmol when HCI salt is present) and R1-CI or R2-CI (1.2 mmol). The resulting suspension is stirred at 1 10 C overnight. Upon completion H20 is added and the aq. phase is extracted with EtOAc (3 times). The combined organic phases are washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure. The residue is purified by column chromatography or by preparative HPLC (conditions C).
Reference： [1]Patent: WO2012/85852,2012,A1 .Location in patent: Page/Page column 71; 85

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