Home Cart 0 Sign in  

[ CAS No. 217448-86-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 217448-86-7
Chemical Structure| 217448-86-7
Structure of 217448-86-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 217448-86-7 ]

Related Doc. of [ 217448-86-7 ]

Alternatived Products of [ 217448-86-7 ]

Product Details of [ 217448-86-7 ]

CAS No. :217448-86-7 MDL No. :MFCD16659092
Formula : C11H9F2N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :XVEURJOWGBWEPY-UHFFFAOYSA-N
M.W : 253.20 Pubchem ID :22716778
Synonyms :

Calculated chemistry of [ 217448-86-7 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.18
Num. rotatable bonds : 4
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.97
TPSA : 57.01 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 1.67
Log Po/w (WLOGP) : 2.23
Log Po/w (MLOGP) : 2.12
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 2.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.65
Solubility : 0.567 mg/ml ; 0.00224 mol/l
Class : Soluble
Log S (Ali) : -2.48
Solubility : 0.836 mg/ml ; 0.0033 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.6
Solubility : 0.0637 mg/ml ; 0.000252 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.32

Safety of [ 217448-86-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 217448-86-7 ]

* 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.

  • Upstream synthesis route of [ 217448-86-7 ]
  • Downstream synthetic route of [ 217448-86-7 ]

[ 217448-86-7 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 106308-60-5 ]
  • [ 922-67-8 ]
  • [ 217448-86-7 ]
YieldReaction ConditionsOperation in experiment
94% With ascorbic acid In ethanol; water at 25℃; Example 7Synthesis of Compound (II)Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate; 2,6-Difluorobenzyl azide (3.0 g, 17.7 mmoles) is suspended in ethanol (30 ml), then methyl propiolate (IV) (1.6 g, 19.6 mmoles), ascorbic acid (317 mg, 1.8 mmoles) and CuSO4 pentahydrate (50 mg, 0.18 mmole) are added. The reaction mixture is kept at 25° C. under stirring overnight. The mixture is concentrated, taken up with ethyl acetate and washed with an ammonia diluted solution. The organic phase is dried, filtered, concentrated under reduced pressure. A crystalline white solid is obtained in 94percent yield.1H NMR (400 MHz, DMSO-d6), δ ppm: 8.86 (s, 1H), 7.52 (m, 1H), 7.27-7.12 (m, 2H), 5.74 (s, 2H), 3.83 (s, 3H).
94% With ascorbic acid In ethanol at 25℃; Example 7; Synthesis of compound (II): Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate 2,6-Difluorobenzyl azide (3.0 g, 17.7 mmoles) is suspended in ethanol (30 ml), then methyl propiolate (IV) (1.6 g, 19.6 mmoles), ascorbic acid (317 mg, 1.8 mmoles) and CuSO4 pentahydrate (50 mg, 0.18 mmole) are added. The reaction mixture is kept at 25°C under stirring overnight. The mixture is concentrated, taken up with ethyl acetate and washed with an ammonia diluted solution. The organic phase is dried, filtered, concentrated under reduced pressure. A crystalline white solid is obtained in 94percent yield. 1H NMR (400 MHz, DMSO-d6), δ ppm: 8.86 (s, 1 H), 7.52 (m, 1H), 7.27-7.12 (m, 2H), 5.74 (s, 2H), 3.83 (s, 3H).
Reference: [1] Patent: US2010/234616, 2010, A1, . Location in patent: Page/Page column 3
[2] Patent: EP2230234, 2010, A1, . Location in patent: Page/Page column 7
[3] ChemSusChem, 2015, vol. 8, # 3, p. 504 - 512
[4] Patent: WO2010/43849, 2010, A1, . Location in patent: Page/Page column 13
[5] Tetrahedron Letters, 2013, vol. 54, # 26, p. 3406 - 3409
  • 2
  • [ 67-56-1 ]
  • [ 106308-60-5 ]
  • [ 471-25-0 ]
  • [ 217448-86-7 ]
YieldReaction ConditionsOperation in experiment
87%
Stage #1: at 10 - 80℃;
Stage #2: at 10 - 65℃; for 7 h;
Example 3
Preparation of methyl-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate [(V), R is methyl].
Mixture of 120 g (0.502 mol) 1-(2, 6-difluorobenzyl)-1H-1, 2, 3-triazole-4-carboxylic acid (IV) and 1000 ml of methanol was stirred at ambient temperature. 25.10 gm sulphuric acid was added slowly followed by addition of 200 ml methanol.
The reaction mixture was heated to 60-65° C. for 6 hours.
Cooled to 10° C. for 1 hour.
Solid was filtered, washed with methanol and dried under reduced pressure.
Yield 111.15 g (87percent); HPLC purity: 99.92percent.
Reference: [1] Patent: US2014/357871, 2014, A1, . Location in patent: Paragraph 0038; 0039
  • 3
  • [ 67-56-1 ]
  • [ 217448-86-7 ]
YieldReaction ConditionsOperation in experiment
87.5% at 60 - 65℃; for 6 h; Mixture of 120 g (0.502 mol) l-(2, 6-difluorobenzyl)-lH-l, 2, 3-triazole-4-carboxylic acid (IV) and 1000 ml of methanol was stirred at ambient temperature. 25.10 gm sulphuric acid was added slowly followed by addition of 200 ml methanol. The reaction mixture was heated to 60-65°C for 6 hours. Cooled to 10°C for 1 hour. Solid was filtered, washed with methanol and dried under reduced pressure. Yield 111.15 g (87percent); HPLC purity: 99.92percent.
Reference: [1] Patent: WO2013/105029, 2013, A1, . Location in patent: Page/Page column 7
  • 4
  • [ 106308-60-5 ]
  • [ 1729-67-5 ]
  • [ 217448-86-7 ]
YieldReaction ConditionsOperation in experiment
19.3 g With triethylamine In isopropyl alcohol at 75 - 80℃; for 25 h; Example 5: Preparation of methyl l-(2, 6-difmorobenzyl)-lH-l,2,3-triazole- 4-carboxylate 2,6-difluorobenzyl azide (20 g), 2,3-dibromo methyl propionate (43.63 g), tri ethyl amine (19.36 g) and isopropyl alcohol (200 ml) were charged in a reaction vessel. The reaction mixture was heated to 75-80°C for 25 hours. The progress of the reaction was monitored by TLC. After completion of the reaction, isopropyl alcohol was evaporated in vacuum to give brown solid to which water was added and extracted using dichloromethane (150 ml). The organic layer was washed with brine, dried on sodium sulphate and evaporated in vacuum below 40°C to give brown solid. This solid was slurried in n-heptane, filtered and dried at 60-65°C to give methyl l-(2, 6-difluorobenzyl)-lH-l,2,3- triazole- 4-carboxylate (19.3g) as light brown solid.
Reference: [1] Patent: WO2014/72992, 2014, A1, . Location in patent: Page/Page column 17
  • 5
  • [ 106308-60-5 ]
  • [ 34846-90-7 ]
  • [ 217448-86-7 ]
Reference: [1] Green Chemistry, 2016, vol. 18, # 18, p. 4947 - 4953
[2] Tetrahedron Letters, 2010, vol. 51, # 24, p. 3229 - 3231
  • 6
  • [ 106308-60-5 ]
  • [ 4519-46-4 ]
  • [ 217448-86-7 ]
YieldReaction ConditionsOperation in experiment
120 g at 75 - 80℃; for 24 h; Example-3
Preparation of methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate
A mixture of 2-(azidomethyl)-1,3-difluorobenzene in t-butanol prepared as per example 2, methyl 2-bromoacrylate (120 gms) and water (200 ml) were heated to 75-80° C.
The contents was stirred at 75-80° C. for 24 hours.
After the completion of reaction, the reaction mixture was cooled to room temperature.
The solid obtained was filtered and then crude mass was added to cyclohexane (240 ml) and the mixture was stirred at room temperature for 2 hours.
The solid was filtered and washed with cyclohexane (50 ml).
The product was dried for 2 hours to give methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate. Yield: 120gms
Reference: [1] Patent: WO2012/25936, 2012, A2, . Location in patent: Page/Page column 9
[2] Patent: US2013/184469, 2013, A1, . Location in patent: Paragraph 0029
  • 7
  • [ 34846-90-7 ]
  • [ 102284-85-5 ]
  • [ 217448-86-7 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 108, p. 88816 - 88820
  • 8
  • [ 106308-60-5 ]
  • [ 922-67-8 ]
  • [ 217448-86-7 ]
Reference: [1] ChemSusChem, 2015, vol. 8, # 3, p. 504 - 512
  • 9
  • [ 106308-60-5 ]
  • [ 5788-17-0 ]
  • [ 217448-86-7 ]
Reference: [1] ChemSusChem, 2013, vol. 6, # 12, p. 2220 - 2225
  • 10
  • [ 85118-00-9 ]
  • [ 217448-86-7 ]
Reference: [1] Patent: WO2012/25936, 2012, A2,
[2] Tetrahedron Letters, 2013, vol. 54, # 26, p. 3406 - 3409
[3] Patent: US2013/184469, 2013, A1,
[4] Patent: WO2014/72992, 2014, A1,
  • 11
  • [ 697-73-4 ]
  • [ 217448-86-7 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 26, p. 3406 - 3409
  • 12
  • [ 106308-60-5 ]
  • [ 217448-86-7 ]
Reference: [1] Patent: WO2013/105029, 2013, A1,
  • 13
  • [ 19064-18-7 ]
  • [ 217448-86-7 ]
Reference: [1] Green Chemistry, 2016, vol. 18, # 18, p. 4947 - 4953
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 217448-86-7 ]

Fluorinated Building Blocks

Chemical Structure| 166196-11-8

[ 166196-11-8 ]

1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid

Similarity: 0.96

Chemical Structure| 113162-36-0

[ 113162-36-0 ]

Methyl 4-fluoro-1H-indole-2-carboxylate

Similarity: 0.58

Chemical Structure| 247564-66-5

[ 247564-66-5 ]

4,6-Difluoroindole-2-carboxylic acid

Similarity: 0.58

Chemical Structure| 348-37-8

[ 348-37-8 ]

Ethyl 6-fluoro-1H-indole-2-carboxylate

Similarity: 0.57

Chemical Structure| 348-32-3

[ 348-32-3 ]

Ethyl 4-fluoro-1H-indole-2-carboxylate

Similarity: 0.57

Aryls

Chemical Structure| 166196-11-8

[ 166196-11-8 ]

1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid

Similarity: 0.96

Chemical Structure| 1824708-16-8

[ 1824708-16-8 ]

1-(2-Chloro-4-cyclopropylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid

Similarity: 0.60

Chemical Structure| 20725-34-2

[ 20725-34-2 ]

1-(4-Bromophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid

Similarity: 0.60

Chemical Structure| 103755-58-4

[ 103755-58-4 ]

(1-Phenyl-1H-1,2,3-triazol-4-yl)methanol

Similarity: 0.57

Chemical Structure| 1450824-22-2

[ 1450824-22-2 ]

(2R,2'R,3R,3'R,4S,4'S,5R,5'R,6S,6'S)-6,6'-Thiobis(4-(4-(3-fluorophenyl)-1H-1,2,3-triazol-1-yl)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,5-diol)

Similarity: 0.55

Esters

Chemical Structure| 499785-52-3

[ 499785-52-3 ]

Ethyl 1-methyl-1H-benzo[d][1,2,3]triazole-5-carboxylate

Similarity: 0.62

Chemical Structure| 113162-36-0

[ 113162-36-0 ]

Methyl 4-fluoro-1H-indole-2-carboxylate

Similarity: 0.58

Chemical Structure| 4967-77-5

[ 4967-77-5 ]

Methyl 1H-1,2,3-triazole-4-carboxylate

Similarity: 0.58

Chemical Structure| 348-37-8

[ 348-37-8 ]

Ethyl 6-fluoro-1H-indole-2-carboxylate

Similarity: 0.57

Chemical Structure| 348-32-3

[ 348-32-3 ]

Ethyl 4-fluoro-1H-indole-2-carboxylate

Similarity: 0.57

Related Parent Nucleus of
[ 217448-86-7 ]

Triazoles

Chemical Structure| 166196-11-8

[ 166196-11-8 ]

1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid

Similarity: 0.96

Chemical Structure| 1824708-16-8

[ 1824708-16-8 ]

1-(2-Chloro-4-cyclopropylphenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid

Similarity: 0.60

Chemical Structure| 20725-34-2

[ 20725-34-2 ]

1-(4-Bromophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid

Similarity: 0.60

Chemical Structure| 4967-77-5

[ 4967-77-5 ]

Methyl 1H-1,2,3-triazole-4-carboxylate

Similarity: 0.58

Chemical Structure| 103755-58-4

[ 103755-58-4 ]

(1-Phenyl-1H-1,2,3-triazol-4-yl)methanol

Similarity: 0.57