Home Cart Sign in  
Chemical Structure| 204319-69-7 Chemical Structure| 204319-69-7

Structure of 204319-69-7

Chemical Structure| 204319-69-7

*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 [ 204319-69-7 ]

CAS No. :204319-69-7
Formula : C5H4F3NOS
M.W : 183.15
SMILES Code : OCC1=NC(C(F)(F)F)=CS1
MDL No. :MFCD09909578
InChI Key :VIGAFTQUOHZWIC-UHFFFAOYSA-N
Pubchem ID :23560688

Safety of [ 204319-69-7 ]

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

Computational Chemistry of [ 204319-69-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 5
Fraction Csp3 0.4
Num. rotatable bonds 2
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 33.24
TPSA ?

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

61.36 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.64
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

1.02
Log Po/w (WLOGP)?

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

2.65
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.

0.36
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

2.98
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.73

Water Solubility

Log S (ESOL):?

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

-1.82
Solubility 2.76 mg/ml ; 0.015 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.9
Solubility 2.32 mg/ml ; 0.0126 mol/l
Class?

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

Very 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

-2.01
Solubility 1.79 mg/ml ; 0.00977 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

Yes
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.

-6.69 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

1.0
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

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)

2.19

Application In Synthesis of [ 204319-69-7 ]

* 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 [ 204319-69-7 ]

[ 204319-69-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 431-35-6 ]
  • [ 204319-69-7 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: for 18 h; Heating / reflux
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol; ethanol at 20℃; for 48 h;
A solution of3-brom-1, 1, 1-trifluoroacetone (3.2 ml, 30.2 mmol) and 2-amino-2- thioxoethyl pivalate (5.3 g, 30.2 mmol) in ethanol (15 ml) was stirred at reflux for 18 h. To the cooled solution were added methanol (10 ml) and DBU (4.6 ml, 30.2 mmol) and the solution was stirred at room temperature for 2 days. The reaction mixture was evaporated in vacuo, extracted with dichloromethane, washed with water, dried overNa2SO4, and evaporated in vacuo to give crude product as a black oil. This was purified by flash column chromatography on silica eluting with 30 percent ethyl acetate in hexane to give the title compound as an off-white solid (3.2 g, 58 percent).IH NMR (400 MHz, DMSO)8 8.42(1H, s), 6.30(1H, t, J5.8), 4.79 (2H, d, J5. 7).
58%
Stage #1: for 18 h; Heating / reflux
Stage #2: With methanol; 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 20℃; for 48 h;
A solution of 3-bromo- 1,1,1 -trifluoroacetone (3.2 ml, 30.2 mmol) and 2-(tert-butylcarbonyloxy) thioacetamide (5.3 g, 30.2 mmol) in ethanol (15 ml) was stirred at reflux for 18 h. To the cooled solution were added methanol (10 ml) and DBU (4.6 ml, 30.2 mmol) and the solution was stirred at room temperature for 2 days. The reaction mixture was evaporated in vacuo, extracted with dichloromethane, washed with water, dried over Na2SO4, and evaporated in vacuo to give crude product as a black oil. Purification by flash column chromatography, eluting with 30 percent ethyl acetate in hexane, gave the title compound as an off-white solid (3.2 g, 58 percent). 1H NMR (400 MHz, DMSO) δ 8.42 (1 H, s), 6.30 (1 H, t, J 5.8), 4.79 (2 H, d, J 5.7).
30%
Stage #1: at 60℃; for 24 h;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 20℃; for 48 h;
To the thioamide, 2-amino-2-thioxoethyl pivalate (3.0 g, 17.02 mmol) (Commercial source: Acros organics) in ethanol (10 ml), 3-bromo-l,l,l-trifluoropropan-2-one (3.23 g, 17.02 mmol) (Commercial source: Apollo scientific) was added and heated at 60°C for 24h. Then reaction mixture was cooled, DBU (2.59g, 17.02 mmol) was added and stirred at rt for 2d. Then volatiles were removed in vacuum, reaction mixture was partitioned between ethyl acetate and water. Organic layer was dried, evaporated and column purified to yield (4- (trifluoromethyl)thiazol-2-yl)methanol in 30percent yield.
References: [1] Patent: WO2005/49613, 2005, A1, . Location in patent: Page/Page column 52.
[2] Patent: WO2006/120481, 2006, A2, . Location in patent: Page/Page column 19.
[3] Patent: WO2012/54510, 2012, A1, . Location in patent: Page/Page column 90.
  • 2
  • [ 79247-86-2 ]
  • [ 204319-69-7 ]
YieldReaction ConditionsOperation in experiment
1.7 g at 0℃; for 2 h; Sodium tetrahydroborate (840 mg) was added to a solution of ethyl 4- (trifluoromethyl) -1, 3-thiazole-2-carboxylate (2.5 g) in methanol (15 ml) at 0°C, and the mixture was stirred at the same temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (1.7 g) . 1H NMR (400 MHz, DMSO-d6) δ 4.78 (2H, d, J = 5.5 Hz), 6.28 (1H, t, J = 5.6 Hz) , 8.41 (1H, s)
References: [1] Patent: WO2015/5489, 2015, A1, . Location in patent: Paragraph 0298.
[2] Patent: WO2018/188795, 2018, A1, . Location in patent: Page/Page column 51-52.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 204319-69-7 ]

Fluorinated Building Blocks

Chemical Structure| 958452-22-7

A813654 [958452-22-7]

2-Methyl-4-(trifluoromethyl)thiazol-5-amine

Similarity: 0.76

Chemical Structure| 117724-63-7

A165993 [117724-63-7]

2-Methyl-4-(trifluoromethyl)thiazole-5-carboxylic acid

Similarity: 0.69

Chemical Structure| 915030-08-9

A112562 [915030-08-9]

2-(Trifluoromethyl)thiazole-4-carboxylic acid

Similarity: 0.65

Chemical Structure| 349-49-5

A159971 [349-49-5]

4-(Trifluoromethyl)thiazol-2-amine

Similarity: 0.63

Chemical Structure| 1314977-20-2

A240098 [1314977-20-2]

(2-Amino-4-(trifluoromethyl)thiazol-5-yl)methanol

Similarity: 0.62

Alcohols

Chemical Structure| 475059-74-6

A582660 [475059-74-6]

(4-(tert-Butyl)thiazol-2-yl)methanol

Similarity: 0.70

Chemical Structure| 50382-32-6

A123688 [50382-32-6]

(2,4-Dimethylthiazol-5-yl)methanol

Similarity: 0.66

Chemical Structure| 14542-12-2

A133062 [14542-12-2]

Thiazol-2-ylmethanol

Similarity: 0.66

Chemical Structure| 1314977-20-2

A240098 [1314977-20-2]

(2-Amino-4-(trifluoromethyl)thiazol-5-yl)methanol

Similarity: 0.62

Chemical Structure| 202932-04-5

A136768 [202932-04-5]

5-Methyl-2-thiazolemethanol

Similarity: 0.62

Trifluoromethyls

Chemical Structure| 958452-22-7

A813654 [958452-22-7]

2-Methyl-4-(trifluoromethyl)thiazol-5-amine

Similarity: 0.76

Chemical Structure| 117724-63-7

A165993 [117724-63-7]

2-Methyl-4-(trifluoromethyl)thiazole-5-carboxylic acid

Similarity: 0.69

Chemical Structure| 915030-08-9

A112562 [915030-08-9]

2-(Trifluoromethyl)thiazole-4-carboxylic acid

Similarity: 0.65

Chemical Structure| 349-49-5

A159971 [349-49-5]

4-(Trifluoromethyl)thiazol-2-amine

Similarity: 0.63

Chemical Structure| 1314977-20-2

A240098 [1314977-20-2]

(2-Amino-4-(trifluoromethyl)thiazol-5-yl)methanol

Similarity: 0.62

Related Parent Nucleus of
[ 204319-69-7 ]

Thiazoles

Chemical Structure| 958452-22-7

A813654 [958452-22-7]

2-Methyl-4-(trifluoromethyl)thiazol-5-amine

Similarity: 0.76

Chemical Structure| 541-58-2

A564732 [541-58-2]

2,4-Dimethylthiazole

Similarity: 0.70

Chemical Structure| 14542-16-6

A148087 [14542-16-6]

4-Methylthiazole-2-carboxylic acid

Similarity: 0.70

Chemical Structure| 475059-74-6

A582660 [475059-74-6]

(4-(tert-Butyl)thiazol-2-yl)methanol

Similarity: 0.70

Chemical Structure| 117724-63-7

A165993 [117724-63-7]

2-Methyl-4-(trifluoromethyl)thiazole-5-carboxylic acid

Similarity: 0.69