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Quality Control of [ 154327-27-2 ] Purity: 97% SDS Specification

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Product Details of [ 154327-27-2 ]

CAS No. :	154327-27-2
Formula :	C₇H₃ClFNS
M.W :	187.62
SMILES Code :	FC1=CC2=C(SC(Cl)=N2)C=C1
MDL No. :	MFCD09749234
InChI Key :	IHMBREJYLPBYSM-UHFFFAOYSA-N
Pubchem ID :	11240896

Safety of [ 154327-27-2 ]

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

Computational Chemistry of [ 154327-27-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	44.59
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	41.13 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.26
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.44
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.51
Log P_o/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.	2.53
Log P_o/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	4.21
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.19

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.78
Solubility	0.0314 mg/ml ; 0.000168 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.	-3.98
Solubility	0.0194 mg/ml ; 0.000104 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	-3.87
Solubility	0.0255 mg/ml ; 0.000136 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	Yes
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.	-5.0 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)	2.28

Application In Synthesis of [ 154327-27-2 ]

* 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 [ 154327-27-2 ]

[ 154327-27-2 ] Synthesis Path-Downstream 1~25

Yield	Reaction Conditions	Operation in experiment
51%	With sulfuryl dichloride; In dichloromethane; at 22℃; for 1.0h;Cooling with ice;	General procedure: GP3-2: 2-mercaptobenzothiazole in 10 volume of anhydrous DCM, was added by sulfuryl chloride (SO2Cl2, 1 volume) under ice-cooled condition. The mixture was stirred at rt for 1 hour, which was monitored by TLC. After consumption of starting material, the mixture was diluted by 30 volume of ether, following quenching carefully by adding water. Stirring was kept for 1 hour to make sure the SO2Cl2 was totally consumed and product was released. Organic layer was collected, neutralized by saturated NaHCO3, dried over Na2SO4 and purified by silica gel chromatograph to give the pure product, which was finally characterized by LC-MS and NMR.; 2-chloro-7-fluorobenzothiazole The title compound was prepared according to GP3-2, which was purified by flash column chromatography using PE/EA (20/1) as eluent to give the colorless oil. (420 mg, 22percent yield) 1H NMR (400 MHz, CDCl3) delta 7.76 (d, J=8.2 Hz, 1H), 7.45 (td, J=8.1, 5.9 Hz, 1H), 7.14 (t, J=8.7 Hz, 1H). 13C NMR (101 MHz, CDCl3) delta 156.11 (d, J=250.1 Hz), 154.27, 153.45 (d, J=2.8 Hz), 127.63 (d, J=7.3 Hz), 123.25 (d, J=17.6 Hz), 118.80 (d, J=3.7 Hz), 111.41 (d, J=18.3 Hz).

2
[ 154327-27-2 ]
(+/-)-methyl trans-2-[(4'-amino-1,1'-biphenyl-4-yl)carbonyl]cyclopentanecarboxylate [ No CAS ]
methyl trans-2-({4'-[(5-fluoro-1,3-benzothiazol-2-yl)amino]-1,1'-biphenyl-4-}carbonyl)cyclopentanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With hydrogenchloride; In 1,4-dioxane; butan-1-ol; at 90℃; for 18.0h;	2-Chloro-5-fluoro-1,3-benzothiazole (29 mg, 0.16 mmol) and methyl trans-2-[(4'-amino-1,1'-biphenyl-4-yl)carbonyl]cyclopentanecarboxylate (50 mg, 0.16 mmol) were combined in 1-butanol. The solution was treated with 4 M HCl in dioxane (4 muL, 0.016 mmol) and heated at 90° C. for 18 h. The reaction mixture was concentrated under reduced pressure. The residue was suspended in methanol, and the resulting solid was collected by filtration and dried in vacuo. The title compound was obtained as a pale yellow solid (55 mg, 77percent); LC-MS m/z 475.3 (MH+), retention time 3.97 minutes.

References: [1]Patent: US2004/224997,2004,A1 .Location in patent: Page 43.

3
[ 155559-81-2 ]
[ 154327-27-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sulfuryl dichloride; at 20 - 60℃; for 100.0h;	Sulfuryl chloride (0.3 mL, 4.41 mmol) was added neat to 5-fluoro-benzothiazole-2-thiol (680 mg, 3.67 mmol). The mixture was stirred at RT for 1 hour, and then heated to 60°C for 40 mins. The resulting solution was cooled to room temperature, and poured onto ice, extracted with EtOAc (3x50 mL), washed with brine and dried over Na2S04. The dried organic layers were concentrated to give 2-chloro-5-fluorobenzo[d]thiazole (520 mg, 2.75 mmol, 75percent). ESI-MS (M+l): 187 calc. for C7H5CIFN4S 186.
51%	With sulfuryl dichloride; In dichloromethane; at 20℃; for 1.0h;Cooling with ice;	General procedure: GP3-1: A solution of 2-halo substituted aniline (1.0 eq), potassium ethyl xanthate (1.2 eq or 2.2 eq,typically 2.2 eq) in 10 volume of anhydrous DMF was heated at 100 0Cor 120 0C for 4 hours under nitrogen. TLC monitored the progress ofreaction. After completion, the reaction mixture was cooled to room temperature,diluted with water (10 volume) and neutralized by 1 M HCl solution to pH 5. Theformed precipitate was collected by filtration, rinsed with water, firstlydried by rotavapor, and then dried by oil pump to afford 2-mercaptobenzothiazole.GP3-2: 2-mercaptobenzothiazole in 10 volume ofanhydrous DCM, was added by sulfuryl chloride (SO2Cl2, 1volume) under ice-cooled condition. The mixture was stirred at rt for 1 hour,which was monitored by TLC. After consumption of starting material, the mixturewas diluted by 30 volume of ether, following quenching carefully by addingwater. Stirring was kept for 1 hour to make sure the SO2Cl2was totally consumed and product was released. Organic layer was collected,neutralized by saturated NaHCO3, dried over Na2SO4and purified by silica gel chromatograph to give the pure product, which wasfinally characterized by LC-MS and NMR.
		Sulfuryl chloride (50 muL, 0.65 mmol) was added neat to <strong>[155559-81-2]5-fluoro-1,3-benzothiazole-2-thiol</strong> (100 mg, 0.54 mmol). The mixture was stirred at ambient temperature for 1 h, then heated at 60° C. for 30 minutes. The resulting solution was cooled to rt, and poured onto ice. The title compound was collected by filtration, washed with water, and dried under vacuum. The solid obtained was used without further purification; LC-MS m/z 188.1 (MH+), ret. time 3.27 min.

With thionyl chloride; N,N-dimethyl-formamide; for 3.0h;

Step 2) Synthesis of 2-chloro-5-fluorobenzo [d] thiazole To a 50 mL of reaction flask were added 5-fluorobenzo [d] thiazole-2-thiol (1.00 g, 5.40 mmol) , thionyl chloride (5 mL) and N, N-dimethylformamide (0.10 mL) . The mixture was refluxed for 3 h and cooled to rt. The mixture was concentrated in vacuo to give a product, which was used directly in the next step.

References: [1]Patent: WO2011/143366,2011,A1 .Location in patent: Page/Page column 57.
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7661 - 7670.
[3]Patent: US2004/224997,2004,A1 .Location in patent: Page 32; 33.
[4]Patent: WO2017/88759,2017,A1 .Location in patent: Paragraph 00233.

4
[ 20358-07-0 ]
[ 154327-27-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; copper; sodium nitrite; In water;	STR159 A solution of 242 g (3.5 mol) of sodium nitrite in 440 ml of water is added dropwise with stirring to a mixture, cooled to -10° C., of 147 g (0.87 mol) of 2-amino-5-fluoro-benzothiazole, 1700 ml of conc. hydrochloric acid and 20 g of copper power and the reaction mixture is stirred at 0° C. for 60 minutes and at 50° C. for a further 60 minutes. It is then extracted with chloroform and the solvent is carefully removed by distillation from the organic phase in a water-jet vacuum. 80 g (49percent of theory) of 2-chloro-5-fluoro-benzothiazole are obtained as a crystalline residue of melting point 69° C.

References: [1]Patent: US5356864,1994,A .
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3044 - 3049.

5
[ 154327-27-2 ]
[ 623-05-2 ]
[ 1146693-14-2 ]

Yield	Reaction Conditions	Operation in experiment
34%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Example 144; 5-[4-(6-Fluoro-benzothiazol-2-yloxy)-benzyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid amideStep A: [4-(6-Fluoro-benzothiazol-2-yloxy)-phenyl]-methanol. A mixture of <strong>[154327-27-2]2-chloro-5-fluorobenzthiazole</strong> (2.2 g, 12.0 mmol), 4-hydroxylbenzyl alcohol (1.48 g, 12.0 mmol) and Cs2CO3 (8.6 g, 26.4 mmol) in DMF (30 mL) was stirred at rt overnight. The reaction was filtered and diluted with CH2Cl2 (200 mL) and concentrated. The crude mixture was purified via silica gel column chromatography (1% to 15% CH3OH/CH2Cl2) to afford the title compound (1.1 g, 34%). MS (ESI): Mass calcd for C14H10NO2SF, 275.0; m/z found, 276.1 [M+H]+

References: [1]Patent: US2009/111794,2009,A1 .Location in patent: Page/Page column 47.

6
[ 154327-27-2 ]
[ 1349184-48-0 ]
[ 1349184-76-4 ]

Yield	Reaction Conditions	Operation in experiment
64%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 180℃; for 2.0h;microwave;	A mixture of (l S,3S)-3-((3-chloropyrazin-2-yl)oxy)cyclobutanaminehydrochloride (see PREPARATION 5 A; 470 mg, 2 mmol), <strong>[154327-27-2]2-chloro-5-fluorobenzo[d]thiazole</strong> (see PREPARATION 6; 374 mg, 2 mmol) and DIEA (570 mg, 4 mmol) in NMP (2 mL) was heated to 180°C for 2 hours in microwave. The reaction mixture was extracted with EtOAc (40 mL) and water, the organic phase was washed with brine and dried over Na2S04. The organic layers were concentrated and purified by silica gel column chromatography to give N-((1S,3S)- 3-((3-chloropyrazin-2-yl)oxy)cyclobutyl)-5-fluorobenzo[d]thiazol-2-amine (450 mg, 1.28 mmol, 64percent yield). ESI-MS (M+l): 351 calc. for Ci5Hi2ClFN4OS 350.

References: [1]Patent: WO2011/143366,2011,A1 .Location in patent: Page/Page column 56.

7
[ 367-30-6 ]
[ 154327-27-2 ]

References: [1]Patent: WO2011/143366,2011,A1 .
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7661 - 7670.
[3]Patent: WO2017/69980,2017,A1 .

8
[ 372-19-0 ]
[ 154327-27-2 ]