351003-49-1|5-Chloro-2-fluorobenzenesulfonyl chloride| Ambeed

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Quality Control of [ 351003-49-1 ] Purity: 98% SDS Specification

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Product Details of [ 351003-49-1 ]

CAS No. :	351003-49-1
Formula :	C₆H₃Cl₂FO₂S
M.W :	229.06
SMILES Code :	O=S(C1=CC(Cl)=CC=C1F)(Cl)=O
MDL No. :	MFCD03094221
InChI Key :	OZKAHSNNKADHTK-UHFFFAOYSA-N
Pubchem ID :	2778273

Safety of [ 351003-49-1 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310
Class:	8
UN#:	3261
Packing Group:	Ⅱ

Computational Chemistry of [ 351003-49-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	44.49
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	42.52 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.85
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	2.67
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.91
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.	2.54
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	2.44
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.68

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.25
Solubility	0.13 mg/ml ; 0.000567 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.	-3.21
Solubility	0.14 mg/ml ; 0.00061 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	-3.84
Solubility	0.033 mg/ml ; 0.000144 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.	-5.8 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	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)	1.97

Application In Synthesis of [ 351003-49-1 ]

* 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 [ 351003-49-1 ]

[ 351003-49-1 ] Synthesis Path-Downstream 1~35

1
[ 351003-49-1 ]
2-amino-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid methyl ester hydrochloride [ No CAS ]
[ 904679-64-7 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3832 - 3849.

2
[ 351003-49-1 ]
C₁₈H₃₀N₄O [ No CAS ]
C₂₄H₃₂ClFN₄O₃S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3292 - 3297.

3
[ 351003-49-1 ]
[ 910606-15-4 ]
C₂₅H₃₂ClFN₄O₃S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3292 - 3297.

4
[ 351003-49-1 ]
[ 910605-32-2 ]
5-chloro-N-cis-{4-[4-(2-cyclopropoxy-phenyl)-piperidin-1-yl]-cyclohexyl}-2-fluoro-benzenesulfonamide [ No CAS ]
5-chloro-N-trans-{4-[4-(2-cyclopropoxy-phenyl)-piperidin-1-yl]-cyclohexyl}-2-fluoro-benzenesulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3930 - 3934.

5
[ 351003-49-1 ]
[ 946605-81-8 ]
5-chloro-2-fluoro-N-cis-(4-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperidin-1-yl}-cyclohexyl)-benzenesulfonamide [ No CAS ]
5-chloro-2-fluoro-N-trans-(4-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperidin-1-yl}-cyclohexyl)-benzenesulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3930 - 3934.

6
[ 351003-49-1 ]
2-[5-chloro-2-(3-diethylamino-propylamino)-benzenesulfonylamino]-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 3832 - 3849.

Yield	Reaction Conditions	Operation in experiment
		The following sulfonyl chlorides may be substituted for benzenesulfonyl chloride of Step One: ... 2-Cyanobenzenesulfonyl chloride 3-(Chlorosulfonyl)benzoic acid 5-Chloro-2-fluorobenzenesulfonyl chloride 4-Chloro-2,5-dimethylbenzenesulfonyl chloride ...

8
[ 351003-49-1 ]
[ 147081-49-0 ]
C₁₅H₂₀ClFN₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃;Cooling;	Example 10 5-Chloro-N-[(3R)-1-cyano-3-pyrrolidinyl]-2-fluorobenzenesulfonamide To a chilled solution of <strong>[351003-49-1]5-chloro-2-fluorobenzenesulfonyl chloride</strong> (0.125 g, 0.546 mmol) and triethylamine (0.3 ml, 2.15 mmol) in DCM (2 mL) was added 1,1-dimethylethyl (3R)-3-amino-1-pyrrolidinecarboxylate (0.080 ml, 0.471 mmol). The reaction mixture was stirred at room temperature overnight. Water (1.5 ml) was added to the reaction mixture with stirring. The mixture was diluted with DCM (2 ml) and water (1.5 ml) and put through a phase separator to dry. Then 4N HCl in 1,4-dioxane (2.0 ml) was added. After 1.5 hours, the reaction was blown down to dryness. The dry material was then diluted with DCM (8 ml), and mixed with DIEA (0.45 mL, 2.58 mmol) and BrCN (0.40 mL, 1.2 mmol). The resultant mixture was stirred at room temperature overnight. The solvent was evaporated under vacuum and the solid purified by preparatory HPLC (without TFA) to afford the title compound (0.0671 g). LC-MS: m/z, 304 (M+H), rt 1.6 min.

References: [1]Patent: US2009/264499,2009,A1 .Location in patent: Page/Page column 11.

9
[ 351003-49-1 ]
[ 2930-05-4 ]
[ 100-46-9 ]
[ 1215721-18-8 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 1079 - 1082.

10
[ 351003-49-1 ]
[ 100-46-9 ]
[ 137688-20-1 ]
[ 1215721-26-8 ]

References: [1]Tetrahedron Letters,2010,vol. 51,p. 1079 - 1082.

11
[ 351003-49-1 ]
[ 75-64-9 ]
[ 1203655-72-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	In tetrahydrofuran; at 0 - 20℃;	A solution of <strong>[351003-49-1]5-chloro-2-fluorobenzene-1-sulfonyl chloride</strong> (2.0 g) in tetrahydrofuran (30 ml) was added to a solution of tert-butylamine (9.15 m.) in tetrahydrofuran (70 ml) at 0 0C. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The precipitate was removed by filtration and the filtrate was concentrated in vacuo to give N-tert-butyl-5-chloro-2-fluoro- benzenesulfonamide (2.2 g, 95% yield) as a white solid.

References: [1]Patent: WO2010/2998,2010,A1 .Location in patent: Page/Page column 96.

12
[ 351003-49-1 ]
[ 6850-57-3 ]
[ 1216845-05-4 ]

References: [1]Organic Letters,2010,vol. 12,p. 2182 - 2185.
[2]Organic Letters,2010,vol. 12,p. 1216 - 1219.

13
[ 351003-49-1 ]
[ 107-11-9 ]
[ 1216845-03-2 ]

References: [1]Organic Letters,2010,vol. 12,p. 2182 - 2185.
[2]Organic Letters,2010,vol. 12,p. 1216 - 1219.

14
[ 351003-49-1 ]
[ 100-82-3 ]
[ 1225040-05-0 ]

References: [1]Organic Letters,2010,vol. 12,p. 2182 - 2185.

15
[ 351003-49-1 ]
[ 2393-23-9 ]
[ 1225040-04-9 ]

References: [1]Organic Letters,2010,vol. 12,p. 2182 - 2185.

16
[ 351003-49-1 ]
C₁₆H₁₉N₃O₂S [ No CAS ]
[ 1400283-54-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5936 - 5941.

17
[ 351003-49-1 ]
[ 76-05-1 ]
[ 1426214-70-1 ]
[ 1279829-87-6 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 2,3-Dichloro-N-[4-(6-chloro-5-cyano-pyrazin-2yl)-phenyl]-benzenesulfonamide (1.0 g) was suspended in a mixture of 5 ml iPrOH and 5 ml 35% hydrazine in water at RT and heated to 120C by microwave irradiation for 20 min under stirring in a sealed vessel. The reaction mixture was left to cool to RT. The precipitate was filtered off and washed with water to give the title compound as a yellow solid after drying under vacuum. The title compound was prepared in 22% yield according to the procedure described in example 1, employing 2,5-dichloro-benzenesulfonyl chloride instead of 2,3-dichloro-benzenesulfonyl chloride as starting material. The following modification was made. The crude reaction mixture was evaporated to dryness, redissolved in DMF and purified by preparative HPLC (C18 reversed phase column, elution with a water/MeCN gradient with 0.1 % TFA). The fractions containing the product were lyophilized to yield the title compound in the form of its salt with trifluoroacetic acid. The title compound was prepared by adapting the procedures described in example 1, employing 5-chloro-2-fluoro-benzenesulfonyl chloride instead of 2,3-dichloro-benzenesulfonyl chloride as starting material. The following modification was made. The crude reaction mixture was evaporated to dryness, redissolved in DMF and purified by preparative HPLC (C18 reversed phase column, elution with a water/MeCN gradient with 0.1 % TFA). The fractions containing the product were lyophilized to yield the title compound in the form of its salt with trifluoroacetic acid. 1H-NMR (DMSO-d6): delta (ppm) = 7.27 (d, J = 8.8 Hz, 2H), 7.55 (t, J = 8.7 Hz, 1H), 7.81 (m, 1H), 7.88 (m, 1H), 8.10 (d, J = 8.8 Hz, 2H), 8.91 (s, 1H), 11.10 (s, 1H). MS (ES+): m/e = 419.0 (M+H), chloro pattern.

References: [1]Patent: EP2570415,2013,A1 .Location in patent: Paragraph 0113; 0120; 0185; 0186; 0186.

18
[ 351003-49-1 ]
[ 214360-73-3 ]
[ 1428182-88-0 ]

References: [1]Patent: WO2013/41502,2013,A1 .Location in patent: Page/Page column 122; 123.
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 73 - 78.

19
[ 351003-49-1 ]
[ 1428182-89-1 ]

References: [1]Patent: WO2013/41502,2013,A1 .
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 73 - 78.

20
[ 351003-49-1 ]
[ 1426214-70-1 ]
N-[4-(3-amino-1H-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]-5-chloro-2-fluorobenzenesulfonamide trifluoroacetate salt [ No CAS ]

References: [1]Patent: WO2013/41502,2013,A1 .

21
[ 351003-49-1 ]
[ 1428182-87-9 ]

References: [1]Patent: WO2013/41502,2013,A1 .
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 73 - 78.

22
[ 351003-49-1 ]
tert-butyl 6-(4-aminophenyl)-3-(bis(tert-butoxycarbonyl)amino)-4-(trifluoromethyl)pyrazolo[3,4-d]pyrimidine-1-carboxylate [ No CAS ]
C₃₃H₃₅ClF₄N₆O₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 20℃; for 16h;	To a solution of 160 mg of tert-butyl 6-(4-aminophenyl)-3-(bis(tert- butoxycarbonyl)amino)-4-trifluoromethyl)-pyrazolo[3,4-d]pyrimidine-1 -carboxylate in 5 ml DCM and 43 muIota pyridine, 63 mg of 5-chloro-2-fluoro-benzenesulfonyl chloride were added. After stirring the reaction mixture for 16 h at RT, the solvents were removed under reduced pressure. The residue was dissolved in 10 ml DCM and 1 ml of TFA and stirred for 2 h at RT. Then toluene was added and the solvents were removed under reduced pressure to yield a brown solid. This crude product was purified by preparative HPLC (C18 reverse phase column, elution with a water/MeCN gradient with 0.1 % TFA). The fractions containing the product were lyophilized to yield the pure title compound in the form of its salt with trifluoroacetic acid. Yield: 23 mg. MS (ES+): m/e = 487.0 (M+H), chloro pattern.

References: [1]Patent: WO2014/140065,2014,A1 .Location in patent: Page/Page column 196.

23
[ 351003-49-1 ]
C₁₇H₈Cl₂F₂N₄O₂S [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 73 - 78.

24
[ 351003-49-1 ]
N-[4-(3-amino-1H-pyrazolo[3,4-b]pyrazin-6-yl)-2-fluorophenyl]-5-chloro-2-fluorobenzenesulfonamide trifluoroacetate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 73 - 78.

25
[ 351003-49-1 ]
C₁₂H₁₁N₅*(x)ClH [ No CAS ]
[ 76-05-1 ]
5-chloro-2-fluoro-N-[4-(3-methyl-1H-pyrazolo[3,4-b]pyrazin-6-yl)phenyl]benzenesulfonamide trifluoroacetate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 73 - 78.

26
[ 351003-49-1 ]
[ 819058-34-9 ]
C₁₈H₁₉BClF₂NO₄S [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 73 - 78.

27
[ 351003-49-1 ]
tert-butyl 6-(4-aminophenyl)-3-[bis(tert-butoxycarbonyl)amino]indazole-1-carboxylate [ No CAS ]
C₃₄H₃₈ClFN₄O₈S [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 73 - 78.

28
[ 351003-49-1 ]
[ 45378-03-8 ]
C₁₁H₁₃ClFNO₂S [ No CAS ]