Home Cart Sign in  
Chemical Structure| 187949-90-2 Chemical Structure| 187949-90-2

Structure of 187949-90-2

Chemical Structure| 187949-90-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 187949-90-2 ]

CAS No. :187949-90-2
Formula : C10H8FN3O2
M.W : 221.19
SMILES Code : NC1=C(C=NN1C1=CC=C(F)C=C1)C(O)=O
MDL No. :MFCD01569434

Safety of [ 187949-90-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 187949-90-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 11
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 54.89
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

81.14 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.38
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.72
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.72
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.56
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.55
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.39

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.67
Solubility 0.471 mg/ml ; 0.00213 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.04
Solubility 0.202 mg/ml ; 0.000912 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.23
Solubility 1.31 mg/ml ; 0.0059 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.43 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.82

Application In Synthesis of [ 187949-90-2 ]

* 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 [ 187949-90-2 ]

[ 187949-90-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 138907-68-3 ]
  • [ 187949-90-2 ]
YieldReaction ConditionsOperation in experiment
95% Ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate (22.18 g, 89 mmol) was suspended in 1 N aqueous solution of LiOH (178 ml_, 178 mmol) and methanol (200 ml_). The reaction mixture was refluxed for 17 hours, allowed to cool to room temperature and filtered. The filtrate was acidified to pH=7 with 2N HCI. A solid was collected by filtration and allowed to dry under reduced pressure to afford the title compound as a pale yellow solid (18.64 g, 95 % yield), which was used without further purification.
Intermediate 9: 5-Amino-1-(4-fluorophenyl)-1 H-pyrazole-4-carboxylic acid. To a suspension of ethyl 5-amino-1-(4-fluorophenyl)-1 H-pyrazole-4-carboxylate (12.1g, 48.5mmol) in ethanol (250ml) was added a solution of lithium hydroxide(5.8g, 242mmol) in water (100ml). The mixture was stirred at reflux for 2.5hr. It was allowed to cool and concentrated to 50% of its volume before 5M hydrochloric acid(47ml) was added. After stirring for 15mins, the resulting white solid was filtered off and further 5M hydrochloric acid (3ml) was added. This was filtered and the combined solids were washed with water and diethyl ether and then dried under vacuum to give the title compound (10.27g).1 H NMR (400 MHz, DMSO-d6) deltappm 12.09 (br. s., 1 H) 7.67 (s, 1 H) 7.54 - 7.60 (m, 2H) 7.34 - 7.41 (m, 2 H) 6.29 (br. s., 2 H).LC-MS Retention Time 2.20mins, MH+ 222.
Intermediate 9; 5-Amiotano-1-(4-fluorophenyl)-1 /-/-pyrazole-4-carboxyliotac acid; To a suspension of ethyl 5-amiotano-1-(4-fluorophenyl)-1 /-/-pyrazole-4-carboxylate (12 1g, 48 5mmol) in ethanol (250ml) was added a solution of lithium hydroxide (5 8g, 242mmol) in water (100ml) The mixture was stirred at reflux for 2 5 hours It was allowed to cool <n="61"/>and concentrated to 50% of its volume before 5M hydrochloric acid (47ml) was added. After stirring for 15 minutes, the resulting white solid was filtered off and further 5M hydrochloric acid (3ml) was added to the filtrate and the resulting solid was filtered and the combined solids were washed with water and diethyl ether and then dried under vacuum to give the title compound (10.27g).1H NMR (400 MHz, DMSOd6) delta ppm 12.09 (br. s., 1 H) 7.67 (s, 1 H) 7.54 - 7.60 (m, 2H) 7.34 - 7.41 (m, 2H) 6.29 (br. s., 2H). LC-MS Retention Time 2.20mins, MH+ 222.
With water; In ethanol;Reflux; General procedure: Intermediates 13 6 was synthesized according to the literature by ML Bender [28]. Intermediates 5 was dissolved in a solution of 15 ethanol and 16 potassium hydroxide and refluxed for 2h. After cooling, the pH of the mixture was adjusted to 5-6by the dropwise addition of 10% 17 HCl solution to give an intermediate 13 6, which was filtered under vacuum and recrystallized from ethanol to give the pure products.
To a suspension of ethyl 5-amino-1-(4-fluorophenyl)-1/-/-pyrazole-4-carboxylate (12.1g, 48.5mmol) in ethanol (250ml) was added a solution of lithium hydroxide (5.8g, 242mmol) in water (100ml). The mixture was stirred at reflux for 2.5 hours. It was allowed to cool and concentrated to 50% of its volume before 5M hydrochloric acid (47ml) was added. After stirring for 15 minutes, the resulting white solid was filtered off and further 5M hydrochloric acid (3ml) was added to the filtrate and the resulting solid was filtered and the combined solids were washed with water and diethyl ether and then dried under vacuum to give the title compound (10.27g).1H NMR (400 MHz, DMSO-Cf6) delta ppm 12.09 (br. s., 1 H) 7.67 (s, 1 H) 7.54 - 7.60 (m, 2H) 7.34 - 7.41 (m, 2H) 6.29 (br. s., 2H).LC-MS Retention Time 2.20mins, MH+ 222.
1.8 g With potassium hydroxide; In isopropyl alcohol; at 80℃; for 5h; To a stirred solution of Step 2 intermediate (2.6 g, 10.42 mmol) in isopropyl alcohol (35 mL) was added potassium hydroxide (880 mg, 15.62 mmol) at RT. The mixture was stirred at 80 C for 5h. The solvent was evaporated under reduced pressure and the residue was acidified with nitric acid till pH 2-3. The precipitated solid was filtered, washed with water (40 mL x 2) and dried under vacuum to yield 1.80 g of the titled product as a solid. lH NMR (300 MHz, DMSO- d6): delta 6.27 (s, 2H), 7.36 (t, = 8.4 Hz, 2H), 7.54-7.60 (m, 2H), 7.66 (s, 1H), 12.07 (br s, 1H); APCI (m/z) 220 (M-H)".
In methanol; The solid was filtered off and dried to give <strong>[138907-68-3]5-amino-4-ethylcarboxy-1-(4-fluorophenyl)pyrazole</strong> (28 g) which was suspended in a mixture of 1N lithium hydroxide (100 ml) and methanol (250 ml). The reaction mixture was heated at reflux. After 16 h, the reaction mixture was filtered through a sinter funnel and the filtrate was acidified with 2 N hydrochloric acid (65 ml). The solid was filtered off and dried to give 5-amino-4-carboxy-1-(4-fluorophenyl)pyrazole (21 g).

  • 2
  • [ 187949-90-2 ]
  • [ 25365-71-3 ]
  • (E)-1-(4-fluorophenyl)-5-(((2-phenyl-1H-indol-3-yl)methylene)amino)-1H-pyrazole-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; water; at 80℃; General procedure: Intermediate 4 (1mmol) and the intermediate 7 (1mmol) were dissolved in ethanol to the glass flask, then HCl solution was added as a catalyst refluxed at 80C for 15-18h. After the TLC monitoring reaction was completed, the mixture was vacuum filtered and concentrated. Finally, the above crude product can be isolated and purified by column chromatography (Hexane/EtOAc=8:1) to obtain target compounds.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 187949-90-2 ]

Fluorinated Building Blocks

Chemical Structure| 138907-68-3

A624979 [138907-68-3]

Ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

Similarity: 0.95

Chemical Structure| 618070-65-8

A406632 [618070-65-8]

Ethyl 5-amino-1-(2-fluorophenyl)-1H-pyrazole-4-carboxylate

Similarity: 0.92

Chemical Structure| 138907-73-0

A191407 [138907-73-0]

Ethyl 1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

Similarity: 0.84

Chemical Structure| 1352625-33-2

A126713 [1352625-33-2]

4-Fluoropyrazolo[1,5-a]pyridine-3-carboxylic acid

Similarity: 0.82

Chemical Structure| 1352625-29-6

A211356 [1352625-29-6]

6-Fluoropyrazolo[1,5-a]pyridine-3-carboxylic acid

Similarity: 0.79

Aryls

Chemical Structure| 138907-68-3

A624979 [138907-68-3]

Ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

Similarity: 0.95

Chemical Structure| 618070-65-8

A406632 [618070-65-8]

Ethyl 5-amino-1-(2-fluorophenyl)-1H-pyrazole-4-carboxylate

Similarity: 0.92

Chemical Structure| 138907-73-0

A191407 [138907-73-0]

Ethyl 1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

Similarity: 0.84

Chemical Structure| 16078-71-0

A189228 [16078-71-0]

Ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate

Similarity: 0.83

Chemical Structure| 15001-11-3

A243599 [15001-11-3]

Ethyl 5-amino-1-(p-tolyl)-1H-pyrazole-4-carboxylate

Similarity: 0.81

Amines

Chemical Structure| 138907-68-3

A624979 [138907-68-3]

Ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

Similarity: 0.95

Chemical Structure| 618070-65-8

A406632 [618070-65-8]

Ethyl 5-amino-1-(2-fluorophenyl)-1H-pyrazole-4-carboxylate

Similarity: 0.92

Chemical Structure| 16078-71-0

A189228 [16078-71-0]

Ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate

Similarity: 0.83

Chemical Structure| 15001-11-3

A243599 [15001-11-3]

Ethyl 5-amino-1-(p-tolyl)-1H-pyrazole-4-carboxylate

Similarity: 0.81

Chemical Structure| 51516-70-2

A114105 [51516-70-2]

5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile

Similarity: 0.77

Carboxylic Acids

Chemical Structure| 1352625-33-2

A126713 [1352625-33-2]

4-Fluoropyrazolo[1,5-a]pyridine-3-carboxylic acid

Similarity: 0.82

Chemical Structure| 1352625-29-6

A211356 [1352625-29-6]

6-Fluoropyrazolo[1,5-a]pyridine-3-carboxylic acid

Similarity: 0.79

Chemical Structure| 1134-50-5

A166041 [1134-50-5]

1-Phenyl-1H-pyrazole-4-carboxylic acid

Similarity: 0.75

Chemical Structure| 16205-46-2

A236058 [16205-46-2]

Pyrazolo[1,5-a]pyridine-3-carboxylic acid

Similarity: 0.74

Chemical Structure| 16205-47-3

A451938 [16205-47-3]

7-Methylpyrazolo[1,5-a]pyridine-3-carboxylic acid

Similarity: 0.73

Related Parent Nucleus of
[ 187949-90-2 ]

Pyrazoles

Chemical Structure| 138907-68-3

A624979 [138907-68-3]

Ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

Similarity: 0.95

Chemical Structure| 618070-65-8

A406632 [618070-65-8]

Ethyl 5-amino-1-(2-fluorophenyl)-1H-pyrazole-4-carboxylate

Similarity: 0.92

Chemical Structure| 138907-73-0

A191407 [138907-73-0]

Ethyl 1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

Similarity: 0.84

Chemical Structure| 16078-71-0

A189228 [16078-71-0]

Ethyl 5-amino-1-phenyl-1H-pyrazole-4-carboxylate

Similarity: 0.83

Chemical Structure| 15001-11-3

A243599 [15001-11-3]

Ethyl 5-amino-1-(p-tolyl)-1H-pyrazole-4-carboxylate

Similarity: 0.81