Home Cart Sign in  
Chemical Structure| 871700-24-2 Chemical Structure| 871700-24-2

Structure of 871700-24-2

Chemical Structure| 871700-24-2

*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 [ 871700-24-2 ]

CAS No. :871700-24-2
Formula : C18H15FIN3O4
M.W : 483.23
SMILES Code : O=C1N(C2=CC=C(I)C=C2F)C3=C(C(O)=C(C)C(N3C)=O)C(N1C4CC4)=O
MDL No. :MFCD18207185
InChI Key :MHHFXMZMCYWCJQ-UHFFFAOYSA-N
Pubchem ID :59717004

Safety of [ 871700-24-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 871700-24-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 27
Num. arom. heavy atoms 16
Fraction Csp3 0.28
Num. rotatable bonds 2
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 107.75
TPSA ?

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

86.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.17
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

2.36
Log Po/w (WLOGP)?

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

2.3
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.

3.17
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

3.0
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.8

Water Solubility

Log S (ESOL):?

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

-4.63
Solubility 0.0113 mg/ml ; 0.0000235 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-3.81
Solubility 0.0747 mg/ml ; 0.000155 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

-4.59
Solubility 0.0125 mg/ml ; 0.0000259 mol/l
Class?

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

Moderately 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

Yes
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.

-7.57 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.

0.55

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

1.0 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)

3.0

Application In Synthesis of [ 871700-24-2 ]

* 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 [ 871700-24-2 ]

[ 871700-24-2 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 871700-24-2 ]
  • [ 358-23-6 ]
  • [ 871700-07-1 ]
YieldReaction ConditionsOperation in experiment
93% With 2,6-dimethylpyridine; In chloroform; at 0 - 20℃; for 2.5h; Under a nitrogen atmosphere, to 3-cyclopropyl-l-(2-fluoro- 4-iodophenyl)-5-hydroxy-6,8-dimethyl-1H,8H-pyrido[2,3- d] pyrimidine-2,4,7-trione 55 (33.0 g) obtained in Step 5 were added chloroform (165 ml) and 2,6-lutidine(10.4 ml), and trifluoromethanesulfonic anhydride 56 (14.4 ml) was added dropwise under ice-cooling with stirring. After the completion of the dropwise addition, the mixture was stirred at same temperature for 30 min and at room temperature for 2 hrs. The reaction mixture was washed successively with aqueous sodium hydrogen carbonate (165 ml), 1N hydrochloric acid (165 ml) and brine (165 ml) and dried over anhydrous magnesium sulfate. Anhydrous magnesium sulfate was filtered off and the filtrate was concentrated under reduced pressure. 2-Propanol (198 ml) was added to the residue, and the mixture was stirred with heating under reflux, and allowed to return to room temperature. The crystals were collected by filtration and dried to give trifluoromethanesulfonic acid 3-cyclopropyl-l-(2-fluoro-4- iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro- pyrido [2,3-d]pyrimidin-5-yl ester 43 (31.9 g, yield 93%) as colorless crystals.
  • 2
  • [ 871700-24-2 ]
  • [ 98-59-9 ]
  • [ 871700-32-2 ]
YieldReaction ConditionsOperation in experiment
91% With trimethylamine hydrochloride; triethylamine; In acetonitrile; at 0 - 20℃; for 4.0h; Under a nitrogen atmosphere, to 3-cyclopropyl-l-(2-fluoro- 4-iodo-phenyl)-5-hydroxy-6,8-dimethyl-1H,8H-pyrido[2,3- d] pyrimidine-2,4,7-trione 55 (23.9 g) was added acetonitrile (167 ml), and the mixture was stirred under ice-cooling. Triethylamine (11.0 ml) and trimethylamine hydrochloride (2.37 g) were added, and a solution of p-toluenesulfonyl chloride 11 (12.3 g) in acetonitrile (72.0 ml) was added dropwise. The mixture was stirred under ice-cooling for 1 hr, and stirred at room temperature for 3 hrs. Methanol (239 ml) was added, and the mixture was stirred at room temperature for 1 hr. The crystals were collected by filtration and dried to give p-toluenesulfonic acid 3-cyclopropyl-1-(2-fluoro-4-iodo-phenyl)-6,8-dimethyl-2,4,7- trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 77 (28.7 g, yield 91%) as colorless crystals.
  • 3
  • [ 871700-22-0 ]
  • [ 516-05-2 ]
  • [ 871700-24-2 ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride; at 100℃; for 3.0h;Product distribution / selectivity; Under a nitrogen atmosphere, to 3-cyclopropyl-l-(2-fluoro- 4-iodo-phenyl)-6-methylamino-1H-pyrimidine-2,4-dione 52 (34.4 g) and 2-methyl-malonic acid 54 (15.2 g) was added acetic anhydride (34.4 ml), and the mixture was stirred with heating at 100C for 3 hrs. After allowing to cool to 50C, acetone (68.8 ml) was added dropwise, and the mixture was stirred as it was for 30 min. Water (172 ml) was further added dropwise, and the mixture was stirred for 1 hr. After allowing to cool to room temperature with stirring, the precipitated crystals were collected by filtration and dried to give crude crystals (37.7 g, LC purity 91%) of 3- cyclopropyl-1-(2-fluoro-4-iodo-phenyl)-5-hydroxy-6,8-dimethyl- lH,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione 55. Isopropanol (92.0 ml) was added to the obtained crude crystals (30.7 g), and the mixture was stirred at room temperature for 4 hrs. The crystals were collected by filtration and dried to give 3-cyclopropyl-l-(2-fluoro-4-iodo-phenyl)-5-hydroxy-6,8-dimethyl-1H,8H-pyrido[2,3- d]pyrimidine-2,4,7-trione 55 (25.9 g, yield from 76,58%) as pale-yellow crystals.
  • 4
  • [ 871700-23-1 ]
  • [ 871700-22-0 ]
  • [ 516-05-2 ]
  • C18H15FIN3O4 [ No CAS ]
  • [ 871700-24-2 ]
YieldReaction ConditionsOperation in experiment
21% With acetic anhydride; at 100℃; for 2.0h;Product distribution / selectivity; To a 2: 1 mixture (34.6 g) of 3-cyclopropyl-l-(2-fluoro-4- iodophenyl)-6-methylamino-lH-pyrimidine-2,4-dione 52 and 1- cyclopropyl-3-(2-fluoro-4-iodo-phenyl)6-methylamino-1H- pyrimidine-2,4, -dione 53 obtained in Step 4, and 2-methylmalonic acid 54 (10.2 g) was added acetic anhydride (173 ml), and the mixture was stirred at 100C for 2 hrs. After allowing to cool to room temperature, the reaction mixture was concentrated under reduced pressure. Acetone (104 ml) was added to the residue, and the mixture was stirred with heating under reflux for 30 min. After allowing to cool to room temperature, the precipitated crystals were collected by filtration and dried to give 3- cyclopropyl-1-(2-fluoro-4-iodophenyl)-5-hydroxy-6,8-dimethyl- lH,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione 55 (15.1 g, yield from 48,21%) as colorless crystals.
  • 5
  • [ 871700-18-4 ]
  • ethyl 1,5-dimethyl-2,4,6-pyridin-3-carboxylate [ No CAS ]
  • [ 871700-24-2 ]
YieldReaction ConditionsOperation in experiment
14.5 g With sodium ethanolate; In tetrahydrofuran; at 0 - 60℃; for 8.0h; S2: N-(2-Fluoro-4-iodophenyl)-N'-cyclopropyl urea (20.8 g, 65.0 mmol)In a solution of THF (300 mL),Sodium ethoxide (12.2 g, 179.3 mmol) was added portionwise at 0 C and allowed to warm to room temperature.The crude solution of 1,5-dimethyl-2,4,6-pyridinetrione-3-carboxylate prepared in the step S1 was dissolved in THF (200 mL), and reacted at 60 C for 8 h, and cooled to room temperature.Concentrated hydrochloric acid to adjust the pH to 2-3, concentrated to give a viscous solid,Dichloromethane (300 mL) was added and washed with water (50 mL once, three times in total).Dry, concentrated,The residue was recrystallized from acetone to give 3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-5-hydroxy-6,8-dimethyl-1H,8H-pyrido[2,3- d]pyrimidine-2,4,7-trione (14.5 g),Yield 47.3%
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 871700-24-2 ]

Fluorinated Building Blocks

Chemical Structure| 871700-22-0

A128495 [871700-22-0]

3-Cyclopropyl-1-(2-fluoro-4-iodophenyl)-6-(methylamino)pyrimidine-2,4(1H,3H)-dione

Similarity: 0.76

Chemical Structure| 959236-96-5

A122058 [959236-96-5]

8-Fluoroquinazoline-2,4(1H,3H)-dione

Similarity: 0.66

Chemical Structure| 76088-98-7

A296916 [76088-98-7]

7-Fluoroquinazoline-2,4(1H,3H)-dione

Similarity: 0.63

Chemical Structure| 832720-36-2

A136268 [832720-36-2]

Sodium (R)-4-((2-(5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-1-phenylethyl)amino)butanoate

Similarity: 0.63

Chemical Structure| 190595-65-4

A104063 [190595-65-4]

(3R,4S)-4-(4-(Benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-oxopropyl)azetidin-2-one

Similarity: 0.59

Aryls

Chemical Structure| 871700-22-0

A128495 [871700-22-0]

3-Cyclopropyl-1-(2-fluoro-4-iodophenyl)-6-(methylamino)pyrimidine-2,4(1H,3H)-dione

Similarity: 0.76

Chemical Structure| 832720-36-2

A136268 [832720-36-2]

Sodium (R)-4-((2-(5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-1-phenylethyl)amino)butanoate

Similarity: 0.63

Chemical Structure| 190595-65-4

A104063 [190595-65-4]

(3R,4S)-4-(4-(Benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-oxopropyl)azetidin-2-one

Similarity: 0.59

Chemical Structure| 391211-97-5

A106226 [391211-97-5]

3,4-Difluoro-2-((2-fluoro-4-iodophenyl)amino)benzoic acid

Similarity: 0.59

Chemical Structure| 830346-47-9

A210259 [830346-47-9]

1-(2-Fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione

Similarity: 0.58

Alcohols

Chemical Structure| 163222-32-0

A115873 [163222-32-0]

(3R,4S)-4-(4-(Benzyloxy)phenyl)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)azetidin-2-one

Similarity: 0.56

Chemical Structure| 1873-59-2

A105077 [1873-59-2]

4-Hydroxy-3-methylquinolin-2(1H)-one

Similarity: 0.56

Chemical Structure| 83846-83-7

A325093 [83846-83-7]

3-(2-(4-(4-Fluorobenzoyl)piperidin-1-yl)ethyl)quinazoline-2,4(1H,3H)-dione (2R,3R)-2,3-dihydroxysuccinate

Similarity: 0.56

Chemical Structure| 452105-23-6

A124138 [452105-23-6]

(S,Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-N-(2-hydroxy-3-morpholinopropyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

Similarity: 0.54

Chemical Structure| 66108-95-0

A514163 [66108-95-0]

N1,N3-Bis(2,3-dihydroxypropyl)-5-(N-(2,3-dihydroxypropyl)acetamido)-2,4,6-triiodoisophthalamide

Similarity: 0.54

Amides

Chemical Structure| 871700-22-0

A128495 [871700-22-0]

3-Cyclopropyl-1-(2-fluoro-4-iodophenyl)-6-(methylamino)pyrimidine-2,4(1H,3H)-dione

Similarity: 0.76

Chemical Structure| 959236-96-5

A122058 [959236-96-5]

8-Fluoroquinazoline-2,4(1H,3H)-dione

Similarity: 0.66

Chemical Structure| 959236-79-4

A185660 [959236-79-4]

8-Iodoquinazoline-2,4(1H,3H)-dione

Similarity: 0.64

Chemical Structure| 61948-86-5

A102345 [61948-86-5]

5-Methoxyquinazoline-2,4(1H,3H)-dione

Similarity: 0.63

Chemical Structure| 76088-98-7

A296916 [76088-98-7]

7-Fluoroquinazoline-2,4(1H,3H)-dione

Similarity: 0.63

Related Parent Nucleus of
[ 871700-24-2 ]

Other Aromatic Heterocycles

Chemical Structure| 635698-34-9

A386469 [635698-34-9]

6-Benzyl-6,7-dihydro-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,5H)-dione

Similarity: 0.54

Chemical Structure| 62459-02-3

A366187 [62459-02-3]

7-Benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione

Similarity: 0.53

Chemical Structure| 135481-57-1

A102008 [135481-57-1]

6-Benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4(1H,3H)-dione

Similarity: 0.53

Chemical Structure| 28721-09-7

A163196 [28721-09-7]

10-Methoxy-5H-dibenzo[b,f]azepine-5-carboxamide

Similarity: 0.53

Chemical Structure| 337909-10-1

A107936 [337909-10-1]

Ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate

Similarity: 0.52