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[ CAS No. 6314-23-4 ] {[proInfo.proName]}

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Chemical Structure| 6314-23-4
Chemical Structure| 6314-23-4
Structure of 6314-23-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6314-23-4 ]

CAS No. :6314-23-4 MDL No. :MFCD00046076
Formula : C5H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :DXFBKDSQMUFYLD-UHFFFAOYSA-N
M.W : 112.13 Pubchem ID :237031
Synonyms :

Calculated chemistry of [ 6314-23-4 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 29.46
TPSA : 38.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.99
Log Po/w (XLOGP3) : -1.14
Log Po/w (WLOGP) : -0.12
Log Po/w (MLOGP) : -0.53
Log Po/w (SILICOS-IT) : 0.06
Consensus Log Po/w : -0.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.15
Solubility : 79.8 mg/ml ; 0.712 mol/l
Class : Very soluble
Log S (Ali) : 0.83
Solubility : 763.0 mg/ml ; 6.8 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.58
Solubility : 29.2 mg/ml ; 0.261 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.41

Safety of [ 6314-23-4 ]

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 [ 6314-23-4 ]

* 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 [ 6314-23-4 ]

[ 6314-23-4 ] Synthesis Path-Downstream   1~45

  • 1
  • [ 288-13-1 ]
  • [ 107-07-3 ]
  • [ 6314-23-4 ]
YieldReaction ConditionsOperation in experiment
General procedure: Heterocycle (0.1 mol) was added into a solution of EtONa (8.16 g, 0.24 mol) in EtOH (30 mL) heated to reflux. After the solution was stirred for 30 min, 2-chloroethanol (8 g, 0.2 mol) was added dropwise. The resulting suspension was filtered, and the residue was concentrated by vacuum. The crude product was purified by column chromatography on silica gel to yield the desired product. (Rf = 0.3 (EA/ CH3OH= 5:1). The esterification procedure was the same as that in the synthesis of N series.
  • 2
  • [ 6314-23-4 ]
  • [ 98-59-9 ]
  • [ 80200-20-0 ]
YieldReaction ConditionsOperation in experiment
With dmap; triethylamine; In 1,2-dichloro-ethane; at 20℃; for 14h; To a solution of 2- (LH-PYRAZOL-1-YL) ethanol (10 g), triethylamine (18.6 ml) and 4- (dimethylamino) pyridine (1.09 g) in 1,2-dichloroethane (100 ml) was added p-toluenesulfonyl chloride (18.7 g) portionwise at ambient temperature. The reaction mixture was stirred for 14 hours, quenched with water, and extracted with 1,2-dichloroethane. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane: ethyl acetate (1: 1 v/v) to give 2- (LH-PYRAZOL-1-YL) ethyl 4- methylbenzenesulfonate (21.242 g) as a yellow oil. 1H-NMR (CDCL3) : 8 2.43 (1H, s), 4.32-4. 41 (4H, m), 6.21 (1H, t, J=2.0 Hz), 7.28 (2H, d, J=8.2 Hz), 7.41 (1H, d, J=2.3 Hz), 7.44 (1H, d, J=1.3 Hz), (+) ESI-MS (m/z): 267 (M+H) +
  • 5
  • [ 6314-23-4 ]
  • [ 80200-14-2 ]
  • 6
  • [ 6314-23-4 ]
  • 1-[2-(4-Oxiranylmethoxy-phenylsulfanyl)-ethyl]-1H-pyrazole [ No CAS ]
  • 7
  • [ 6314-23-4 ]
  • [ 80200-52-8 ]
  • 8
  • [ 136918-14-4 ]
  • [ 6314-23-4 ]
  • [ 121751-71-1 ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 2h; To a solution of 2- (LH-PYRAZOL-1-YL) ethanol (18.5 g), phthalimide (24.2 g) and triphenylphosphine (47.7 g) in tetrahydrofuran (650 ml) was added diisopropyl azodicarboxylate (36.8 g) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated. To the residue was added ethyl acetate and washed with 2N aqueous hydrochloric acid solution (x 5). The combined aqueous layers were adjusted to pH 7 with 10% aqueous sodium carbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to give 1- (2- PHTHALIMIDOETHYL)-LH-PYRAZOLE (20.02 g) as a solid. H-NMR (DMSO-d6) 8 3.93 (2H, t, J = 5.9 Hz), 4.39 (2H, t, J = 5.9 Hz), 6.16 (1H, dd, J = 2. 1,1. 4 Hz), 7.31 (1H, d, J = 1.4 Hz), 7. 71. (1H, d, J = 2. 1 Hz), 7.79-7. 88 (4H, m). MS (ESI) 264. 3 (M+NA+).
  • 9
  • 2-[4-(5-trifluoromethyl-pyridyl-2-oxy)-phenoxy]-propionyl chloride [ No CAS ]
  • [ 6314-23-4 ]
  • 2-(pyrazol-1-yl)-ethyl 2-[4-(5-trifluoromethylpyridyl-2-oxy)-phenoxy]-propionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In toluene; EXAMPLE 1 STR111 A solution of 8.6 g (0.025 mol) of 2-[4-(5-trifluoromethylpyridyl-2-oxy)-phenoxy]-propionyl chloride in 35 ml of toluene was added to a solution of 2.8 g (0.025 mol) of <strong>[6314-23-4]1-(2-hydroxyethyl)-pyrazole</strong> and 2.8 g (0.0275 mol) of triethylamine in 50 ml of toluene at 0 to 5 C., while stirring. The mixture was stirred at room temperature for a further 16 hours and was then worked up by first adding toluene and then washing successively with dilute hydrochloric acid and water, drying and concentrating under reduced pressure. The residue which remained was freed from traces of volatile constituents by slightly warming under a high vacuum. 7.5 g (71.3% of theory) of 2-(pyrazol-1-yl)-ethyl 2-[4-(5-trifluoromethylpyridyl-2-oxy)-phenoxy]-propionate were obtained in this manner in the form of a yellow oil of refractive index nD21.5 =1.5258.
  • 10
  • iron(II) chloride tetrahydrate [ No CAS ]
  • [ 64-17-5 ]
  • [ 6314-23-4 ]
  • [ 844640-41-1 ]
  • 11
  • copper(II) choride dihydrate [ No CAS ]
  • [ 6314-23-4 ]
  • [ 656247-05-1 ]
  • 12
  • [ 21797-13-7 ]
  • [ 6314-23-4 ]
  • [Pd(1-(2-hydroxyethyl)pyrazole)4](BF4)2 [ No CAS ]
  • 13
  • [ 14104-20-2 ]
  • [ 680183-59-9 ]
  • [ 6314-23-4 ]
  • [Pd(1-(2-hydroxyethyl)pyrazole)4](BF4)2 [ No CAS ]
  • 14
  • [ 21264-30-2 ]
  • [ 6314-23-4 ]
  • [ 680183-59-9 ]
  • 15
  • [ 6314-23-4 ]
  • [ 350-46-9 ]
  • [ 689152-76-9 ]
YieldReaction ConditionsOperation in experiment
A mixture of 2- (LH-PYRAZOL-1-YL) ethanol (6.76 g) and potassium tert-butoxide (6.75 g) in tetrahydrofuran (100 ml) was stirred at ambient temperature for an hour. A solution of 1-fluoro-4-nitrobenzene (7.1 g) in tetrahydrofuran (5 ml) was added to the above mixture and refluxed under stirring for 2.5 hours. The reaction mixture was poured into a mixture of ethyl acetate and water, and the organic layer was washed with brine and dried over magnesium sulfate. The solvent was concentrated in vacuo and the precipitate was collected by filtration to give 1- [2- (4-NITROPHENOXY) ETHYL]-LH-PYRAZOLE (10.75 G). 1H-NMR (DMSO-d6): 8 4. 47-4.60 (4H, m), 6.27 (1H, m), 7.08-7. 16 (2H, m), 7.49 (1H, d, J=1.7 Hz), 7.81 (1H, d, J=2.0 Hz), 8.16- 8.23 (2H, m)
  • 16
  • [ 4548-45-2 ]
  • [ 6314-23-4 ]
  • [ 689152-90-7 ]
YieldReaction ConditionsOperation in experiment
A mixture of 2- (LH-PYRAZOL-1-YL) ethanol (5.41 g) and potassium tert-butoxide (5.41 g) in tetrahydrofuran (50 ml) was stirred at ambient temperature for an hour. 2-Chloro-5- nitropyridine (6.38 g) was added to the above mixture and the resultant mixture was stirred at ambient temperature for 6.5 hours. The reaction mixture was poured into a mixture of ethyl acetate and water, and the organic layer was washed with brine and dried over magnesium sulfate. The solvent was concentrated in vacuo and the residue was chromatographed on silica gel eluting with ethyl acetate and n-hexane (6: 4 v/v). The fraction was concentrated in vacuo and the precipitate was collected by filtration to give 5-nitro-2- [2- (lH-pyrazol-l- yl) ethoxy] pyridine (6.48 g). 1H-NMR (DMSO-d6): 8 4.55 (2H, t, J=4.9 HZ), 4.76 (2H, t, J=4.9 HZ), 6.23-6. 25 (1H, m), 7.10 (1H, d, J=9.2 Hz), 7.45 (1H, d, J=1.7 Hz), 7.78 (1H, d, J=2.3 Hz), 8.46 (1H, dd, J=2.8 Hz, 9.2 Hz), 9.07 (1H, d, J=2.8 Hz)
  • 17
  • [ 288-13-1 ]
  • [ 107-07-3 ]
  • [ 1238621-93-6 ]
  • [ 6314-23-4 ]
  • 18
  • [ 1259878-92-6 ]
  • [ 6314-23-4 ]
  • [ 1259877-25-2 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In 1,4-dioxane; at 20℃; for 1h; EXAMPLE 9: Synthesis of 5-amino-4-(6-methylpyridin-2-yl)-2-(2-pyrazol-1-yl-ethoxy)- thieno[2,3-d]pyrimidine-6-carboxamide (no. 27); 67 mg (0.60 mmol) of <strong>[6314-23-4]1-(2-hydroxyethyl)-1H-pyrazole</strong> and 84 mg (0.75 mmol) of potassium tert-butoxide were added to a slurry of 174 mg (0.50 mmol) of 5-amino-2-methanesulfinyl-4- (6-methylpyridin-2-yl)thieno[2,3-d]pyrimidine-6-carboxamide in 1 ml of dioxane, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, which was then filtered with suction. The residue was washed with water, dried in vacuum and chromatographed on a silica-gel column with dichloromethane/methanol as eluent, giving 5-amino-4-(6-methylpyridin-2-yl)-2-(2-pyrazol-1 -yl-ethoxy)thieno[2,3- d]pyrimidine-6-carboxamide as red crystals; HPLC-MS: [M+H] 396. 1H-NMR (de-DMSO): delta [ppm] = 2.64 (s, 3H), 4.59 (t, J = 5.2 Hz, 2H), 4.83 (t, J = 5.2 Hz, 2H), 6.24 (t, J = 2 Hz, 1 H), 7.19 (bs, 2H), 7.46 (d, J = 2 Hz, 1 H), 7.57 (d, J = 7.7 Hz, 1 H), 7.81 (d, J = 2 Hz, 1 H), 8.04 (t, J = 7.8 Hz, 1 H), 8.20 (d, J = 7.9 Hz1 1 H), 8.38 (bs, 2H)
  • 19
  • [ 6314-23-4 ]
  • [ 1346818-66-3 ]
YieldReaction ConditionsOperation in experiment
38% PREPARATION 642-(5-lodo-pyrazol-1 -yl)-ethanol
  • 20
  • [ 6314-23-4 ]
  • [Pd(1-(2-hydroxyethyl)pyrazole)4](BF4)2 [ No CAS ]
  • 21
  • [ 35213-00-4 ]
  • [ 6314-23-4 ]
  • [ 1093207-55-6 ]
YieldReaction ConditionsOperation in experiment
89.2% Example 231b 2-(2-(1H-pyrazol-1-yl)ethoxy)-6-nitrobenzonitrile Prepared as in Example 197197c from <strong>[6314-23-4]2-(1H-pyrazol-1-yl)ethanol</strong> and 2,6-dinitrobenzonitrile in 89.2% yield. MS 259 (MH+).
  • 22
  • [ 6314-23-4 ]
  • C20H24N4O3 [ No CAS ]
  • 23
  • [ 6314-23-4 ]
  • C11H21BrN2OSi [ No CAS ]
  • 24
  • [ 6314-23-4 ]
  • C12H21BrN2O3Si [ No CAS ]
  • 25
  • [ 6314-23-4 ]
  • C15H26BrN3O2Si [ No CAS ]
  • 26
  • [ 6314-23-4 ]
  • C20H26N4O4 [ No CAS ]
  • 27
  • [ 6314-23-4 ]
  • C9H12BrN3O2 [ No CAS ]
  • 28
  • [ 18162-48-6 ]
  • [ 6314-23-4 ]
  • C11H22N2OSi [ No CAS ]
  • 29
  • [ 6314-23-4 ]
  • [ 864723-36-4 ]
  • 2-(4-formyl-1H-pyrazol-1-yl)ethyl acetate [ No CAS ]
  • 31
  • [ 6314-23-4 ]
  • [ 96450-53-2 ]
YieldReaction ConditionsOperation in experiment
75% With trichlorophosphate; In N,N-dimethyl-formamide; at 90 - 100℃; for 1h; General procedure: 30 g (0.2 mol) of phosphorus oxychloride was added to a mixture of 11.2 g of (0.1 mol) of <strong>[6314-23-4]2-(1H-pyrazol-1-yl)ethanol</strong> I and 95.0 g (0.6 mol) of DMF upon stirring at 90C (maintaining the temperature below 120C). The reaction mixture was stirred during 1 hour at 100C, cooled, and neutralized with aqueous Na2CO3. The reaction product was extracted with chloroform and dried over magnesium sulfate. After removing the solvent, the residue was distilled in vacuum. Yield 9.7 g (75%), bp 47-48C (1 mmHg), nD20 1.5020, d420 1.1190 g/mL. IR spectrum, nu, cm-1: 1520 (ring). 1HNMR data coincided with that in [6].
  • 32
  • [ 108-05-4 ]
  • [ 6314-23-4 ]
  • 2-(1H-pyrazol-1-yl)ethyl acetate [ No CAS ]
  • 33
  • [ 884494-84-2 ]
  • [ 6314-23-4 ]
  • methyl 2-(2-(1H-pyrazol-1-yl)ethoxy)-4-iodonicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.46 g With sodium hydride; In tetrahydrofuran; mineral oil; at 0℃; for 0.333333h;Inert atmosphere; To a solution of methyl 2-fluoro-4-iodonicotinate (0.50 g) obtained in Reference Example 40 and <strong>[6314-23-4]2-(1H-pyrazol-1-yl)ethanol</strong> (0.98 g) in THF (10 mL) was added 60% sodium hydride (0.32 g) at 0C, and the mixture was stirred under an argon atmosphere at the same temperature for 20 min. To the reaction solution was added water, and the mixture was diluted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by NH silica gel chromatography (hexane-ethyl acetate) to give the title compound (0.46 g). 1H NMR (300 MHz, DMSO-d6) delta 3.80 (3H, s), 4.39-4.49 (2H, m), 4.54-4.64 (2H, m), 6.23 (1H, t, J = 2.1 Hz), 7.43 (1H, d, J = 1.9 Hz), 7.53 (1H, d, J = 5.7 Hz), 7.63 (1H, d, J = 2.3 Hz), 7.92 (1H, d, J = 5.3 Hz).
  • 34
  • [ 1206515-76-5 ]
  • [ 6314-23-4 ]
  • [ 1562526-45-7 ]
  • 35
  • [ 6314-23-4 ]
  • [ 1562526-48-0 ]
  • 36
  • [ 6314-23-4 ]
  • 2-(2-(1H-pyrazol-1-yl)ethyl)-6-hydroxy-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
  • 37
  • [ 6314-23-4 ]
  • 2-(4-(1,3-dimethyl-1H-pyrazol-4-yl)benzyl)-4-(2-(1H-pyrazol-1-yl)ethoxy)-1,2-dihydro-3H-pyrrolo[3,4-c]pyridin-3-one [ No CAS ]
  • 38
  • [ 6314-23-4 ]
  • C13H13N3O4 [ No CAS ]
  • 39
  • [ 6314-23-4 ]
  • methyl 2-(2-(1H-pyrazol-1-yl)ethoxy)-4-vinylnicotinate [ No CAS ]
  • 40
  • [ 83860-51-9 ]
  • [ 6314-23-4 ]
  • C21H34N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide; In chloroform; at 80℃; for 12h;Sealed tube; General procedure: A flame-dried Schlenk test tube with a magnetic stirring bar was charged with CuI (0.038 mg, 0.0002 mol), Cs2CO3 (0.65 g, 0.002 mol), heterocycle (0.0014mol), 1-bromo-4-methoxybenzene (0.185 g, 0.001 mol) and DMF (10 mL) under N2. A rubber septum was replaced with a glass stopper, and the system was then evacuated twice and back filled with N2. After being stirred at 120 C for 24 h, the reaction mixture was diluted with 2-3 mL of ethyl acetate, filtered through a plug of silica gel, and washed with 30-50 mL of ethyl acetate. The filtrate was concentrated and the resulting residue was purified by column chromatography on silica gel to provide the desired product. A solution of BBr3 (0.23 mL, 0.0025mol) in CH2Cl2 (5 mL) was added dropwise to the solution of 1-(4-methoxyphenyl)-1H-heterocycle (0.001 mol) in CH2Cl2 (10 mL) cooled to 0 C. The resulting solution was stirred for 4 h at room temperature. And the solution was washed by NaHCO3, NH4Cl, NaCl solution in sequence. The CH2Cl2 was dried over anhydrous sodium sulfate, removed under vacuum, and the residue was purified by chromatography on silica gel to yield the 4-(1H-heterocycle -1-yl)phenol.4-(1H-heterocycle -1-yl)phenol (0.001 mol), N,N?-dicyclohexyl carbodiimide (DCC) (0.0012 mol), 4-dimethylaminopyridine (DMAP) (0.0002 mol) in 10 mL chloroform were placed in a Pyrex glass tube, sealed and heated at 80 C for 12 h. After cooling to room temperature, the white solid was filtrated off, and the solvent was removed under vacuum. The crude product was purified by chromatography on silica gel with to gain the desired products.
  • 41
  • [ 6314-23-4 ]
  • 5-[[2-[2-(2-hydroxyethyl)pyrazol-3-yl]pyridin-3-yl]methoxy]-2-methoxypyridine-4-carbaldehyde [ No CAS ]
  • 42
  • [ 5419-55-6 ]
  • [ 6314-23-4 ]
  • C5H9BN2O3 [ No CAS ]
  • 43
  • [ 6314-23-4 ]
  • [ 101395-71-5 ]
  • 44
  • [ 6314-23-4 ]
  • [ 1093207-54-5 ]
  • 45
  • [ 6314-23-4 ]
  • [ 1093201-58-1 ]
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