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Chemical Structure| 6684-39-5
Chemical Structure| 6684-39-5
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Product Details of [ 6684-39-5 ]

CAS No. :6684-39-5 MDL No. :MFCD03541049
Formula : C5H3Cl2NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :QXZKKHONVQGXAK-UHFFFAOYSA-N
M.W :212.05 Pubchem ID :2792792
Synonyms :

Calculated chemistry of [ 6684-39-5 ]

Physicochemical Properties

Num. heavy atoms : 11
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 : 42.33
TPSA : 55.41 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.46
Log Po/w (XLOGP3) : 1.84
Log Po/w (WLOGP) : 2.74
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : 1.58
Consensus Log Po/w : 1.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.65
Solubility : 0.473 mg/ml ; 0.00223 mol/l
Class : Soluble
Log S (Ali) : -2.62
Solubility : 0.504 mg/ml ; 0.00238 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.19
Solubility : 0.137 mg/ml ; 0.000647 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 6684-39-5 ]

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

Application In Synthesis of [ 6684-39-5 ]

* 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 [ 6684-39-5 ]
  • Downstream synthetic route of [ 6684-39-5 ]

[ 6684-39-5 ] Synthesis Path-Upstream   1~7

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Reference: [1] DRP/DRBP Org.Chem.,

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YieldReaction ConditionsOperation in experiment
98% With ammonia In 1,4-dioxane at -5 - 20℃; for 1 h; 6-Chloro-pyridine-3-sulfonyl chloride (5.Og, 0.024mol) was dissolved in a 0.5M solution of ammonia in dioxane (125mL) at -50C. The mixture was allowed to warm to room temperature and the mixture stirred for 1 hour. The mixture was EPO <DP n="17"/>filtered through celite , washed twice with dioxane and concentrated in vacuo to afford 6-choro-pyridine-3-sulfonic acid amide as an off white solid 4.55g (98percent yield). LC (at)UV215nm; Rt 1.05: 100percent, m/z (ES+): 193/195 (400 MHz; d6-DMSO) 8.79 (IH, d), 8.21 (IH, dd), 7.75 (IH, d) 7.70 (2H, br S)
98% With ammonia In 1,4-dioxane at -5 - 20℃; for 1 h; 6-Chloro-pyridine-3-sulfonic acid amide; 6-Chloro-pyridine-3-sulfonyl chloride (5.Og, 0.024mol) was dissolved in a 0.5M solution of ammonia in dioxane (125mL) at -5°C. The mixture was allowed to warm to room temperature and the mixture stirred for 1 hour. The mixture was filtered through celite", washed twice with dioxane and concentrated in vacuo to afford -choro-pyridine-S-sulfonic acid amide as an off white solid 4.55g (98percent yield). LC (at)UV215nm; Rt 1.05: 100percent, m/z (ES+): 193/195 (400 MHz; d6-DMSO) 8.79 (IH, d), 8.21 (IH, dd), 7.75 (IH, d) 7.70 (2H, br S).
69% With ammonia In water at 20℃; for 2 h; 6-chloropyridine-3-sulfonyl chloride (4.1 g, 19.3 mmol) was stirred in ammonium hydroxide (30 mL) at room temperature for 2 hr. The reaction mixture was diluted with EtOAc (150 mL) and any insoluble material filtered. The filtrate was transferred to a separatory funnel and the phases were separated. The aqueous phase was further extracted with EtOAc (1 x 15 mL). The combined EtOAc extractions were washed with H2O (1 x 50 mL), saturated NaCl (1 x 50 mL), dried (N aaSO-O, and concentrated in vacuo to give 6-chloropyridine-3-sulfonamide (2.58g, 69percent). MS (EI) for C5H3Cl2NO2S: 190.9 (MH-).
69% With ammonia In water at 20℃; for 2 h; β-chloropyridine-S-sulfonamide. 6-chloropyridine-3-sulfbnyl chloride (4.1 g, 19.3 mmol) was stirred in ammonium hydroxide (30 niL) at room temperature for 2 hr. The reaction mixture was diluted with EtOAc (150 mL) and any insoluble material filtered. The filtrate was transferred to a separatory funnel and the phases were separated. The aqueous phase was further extracted with EtOAc (1 x 15 mL). The combined EtOAc extractions were washed with H2O (1 x 50 mL) and saturated NaCl (1 x 50 mL), dried over Na2SO4, and concentrated in vacuo to give 6-chloropyridine-3 -sulfonamide (2.58 g, 69percent). MS (EI) m/z for C5H5Cl2N2O2S: 190.9 (MHT).
69% With ammonia In water at 20℃; for 2 h; 6-chloropyridine-3-sulfonyl chloride (4.1 g, 19.3 mmol) was stirred in ammonium hydroxide (30 mL) at room temperature for 2 hr. The reaction mixture was diluted with EtOAc (150 mL) and any insoluble material filtered. The filtrate was transferred to a separatory funnel and the phases were separated. The aqueous phase was further extracted with EtOAc (1 x 15 mL). The combined EtOAc extractions were washed with H2O (1 x 50 mL) and saturated NaCl (1 x 50 mL), dried over Na2SO4, and concentrated in vacuo to give 6-chloropyridine-3-sulfonamide (2.58 g, 69percent). MS (EI) m/z for C5H5Cl2N2O2S: 190.9 (MHO.

Reference: [1] Patent: WO2008/49605, 2008, A1, . Location in patent: Page/Page column 15-16
[2] Patent: WO2008/138594, 2008, A1, . Location in patent: Page/Page column 16
[3] Patent: WO2008/21389, 2008, A2, . Location in patent: Page/Page column 253
[4] Patent: WO2007/44729, 2007, A2, . Location in patent: Page/Page column 186
[5] Patent: WO2008/127594, 2008, A2, . Location in patent: Page/Page column 376

[6] Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 105,115
[7] Journal of the American Chemical Society, 1949, vol. 71, p. 387,389
[8] Patent: WO2004/48367, 2004, A1, . Location in patent: Page 11
[9] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 9, p. 3307 - 3319
[10] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3947 - 3953
[11] Patent: WO2015/187088, 2015, A1, . Location in patent: Page/Page column 124
[12] Patent: WO2015/148854, 2015, A1, . Location in patent: Paragraph 00478
[13] Patent: US2018/291058, 2018, A1, . Location in patent: Paragraph 0266-0268
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YieldReaction ConditionsOperation in experiment
77%
Stage #1: With hydrogenchloride; sodium nitrite In water; acetic acid at 10 - 15℃; for 1 h;
Stage #2: With sulfur dioxide; copper dichloride In water; acetic acid at 5℃; for 0.166667 h;
A solution of 10 g (79.2 mmol) of 3-amino-6-chloropyridine in concentrated HCl (16 mL) and glacial acetic acid (89 mL) was cooled to 10° C. in an ice batch. 5.46 g (79.2 mmol) of sodium nitrite were added portionwise keeping the temperature below 15° C. The mixture was stirred for 1 h, then added dropwise to a solution of sulfur dioxide (car 27 mL), 2.77 g (16.2 mmol) of copper (II) chloride dihydrate and acetic acid (59 mL) in water (11 mL) over 10 min at 5° C. The reaction mixture was allowed to warm to room temperature and poured over ice/water (300 mL) and stirred for a further 15 min. The resultant precipitate was isolated by filtration, washed with water (2.x.100 mL) and dried under reduced pressure to afford 12.99 g of 6-chloro-pyridine-3-sulfonyl chloride; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.62 (1H, d, J=8.31 Hz), 8.26 (1H, dd, J=8.56, 2.69 Hz), 9.04 (1H, d, J=2.69 Hz).
67%
Stage #1: With hydrogenchloride; sodium nitrite In water; trifluoroacetic acid at -10℃;
Stage #2: With sulfonic acid; copper(l) chloride; copper dichloride In water; acetic acid; trifluoroacetic acid at -10℃; for 0.5 h;
6-chloropyridine-3-sulfonyl chloride. At -10 0C, a solution Of NaNO2 (698 mg, 10.1 mmol) in water (12 mL) was added dropwise to a solution of 5-amino-2-chloropyridine (1.0 gm, 7.78 mmol) in TFA (26 mL) and cone. HCl (2.6 mL). This is solution 1. To a solution of CuCl2 (0.52 gm, 3.89 mmol) in acetic acid (50 mL) was added CuCl (23 mg, 0.23 mmol) followed by dropwise addition of sulfonic acid (26 mL). The reaction solution was cooled to -10 0C. This is solution 2. Solution 1 was added dropwise to solution 2. The reaction was continued to stir at -10 0C for 30 minutes. The reaction mixture was diluted with ethyl acetate (150 mL) and washed with water (150 mL). The organic phase was dried over MgSO4. After evaporating the solvents under reduced pressure, purification via silica gel chromatography using 10-15percent EtOAc in hexane gave 6-chloropyridine-3-sulfonyl chloride as a white solid (l.lg, 67 percent). LC/MS (10percent-99percent CH3CN (0.035percent TFA)/H2O (0.05percent TFA)), m/z: M+l obs = 211.7; tR = 1.3 min.
62%
Stage #1: With hydrogenchloride; sodium nitrite In water at -5 - 0℃;
Stage #2: With thionyl chloride; copper(l) chloride In water
In a 250mL three neck round bottom flask equipped with an overhead stirrer was charged 27mL water, and cooled to -3° C (ice/NaCl). Thionyl chloride (4.52mL, 61.96mmol, 4.5eq) was added slowly so the temperature did not exceed 7° C. The ice bath was removed, allowed to warm to room temperature, then 0.07g (0.69mmol, 0.05 eq) of copper (I) chloride was added. The mixture was then recooled to -5° 5-Amino-2-chloropyridine (1.77g, 13.67mmol) was dissolved in 14 mL of concentrated HCl and cooled to -5° C to which a solution of 1.04g (15.14 mmol, 1.1eq) NaNO2 in 12mL of water was added slowly so the temperature was maintained between -5 and 0°C. This mixture was then added to the thionyl chloride/water/CuCl mixture. A frothing precipitate resulted and was allowed to stir for another 30 min. The product was filtered and air dried. Solids were taken up in ethyl acetate, washed with brine, dried over MgSO4 and concentrated in vacuo to afford 1.7g (62percent) of 6-chloro-pyridine-3-sulfonyl chloride as a light tan solid. Electrospray Mass Spec 210.9 (M+H)+
60.5%
Stage #1: With hydrogenchloride; acetic acid; sodium nitrite In water at 15℃;
Stage #2: With sulfur dioxide; acetic acid In water at 5 - 20℃;
Sodium nitrite (3.45g, 0.05mol) was added portion wise to a stirred solution of 6- chloro-pyridin-3-ylamine (6.4g, 0.05mol) in acetic acid (56ml) and HCl (cone)(9.92ml) while maintaining the temperature below 15°C. This solution was then added drop wise to a stirred solution of sulfur dioxide (17.2g, 0.27mol), copper (II) chloride (1.85g, 0.01 lmol) and water (2.2ml) in acetic acid (37ml) at 5°C. The reaction mixture was allowed to warm to room temperature and poured over ice water and stirred for a further 15min. The resultant precipitate was collected by filtration, washed with water and dried overnight in a vacuum oven to give 6- chloro-pyridine-3-sulfonyl chloride (6.41g, 60.5percent yield); (400 MHz; d6-DMSO) 8.54 (IH, d), 7.96 (IH, dd), 7.50 (IH, d).
60.5% With hydrogenchloride; sulfur dioxide; acetic acid; copper dichloride; sodium nitrite In water at 15 - 20℃; 6-Chloro-pyridine-3-sulfonyl chloride; Sodium nitrite (3.45g, 0.05mol) was added portion wise to a stirred solution of 6- chloro-pyridin-3-ylamine (6.4g, 0.05mol) in acetic acid (56ml) and HCl (cone) (9.92ml) while maintaining the temperature below 15°C. This solution was then added drop wise to a stirred solution of sulfur dioxide (17.2g, 0.27mol), copper (II) chloride (1.85g, 0.01 lmol) and water (2.2ml) in acetic acid (37ml) at 5°C. The reaction mixture was allowed to warm to room temperature and poured over ice water and stirred for a further 15min. The resultant precipitate was collected by filtration, washed with water and dried overnight in a vacuum oven to give 6- chloro-pyridine-3-sulfonyl chloride (6.41g, 60.5percent yield); (400 MHz; d6-DMSO) 8.54 (IH, d), 7.96 (IH, dd), 7.50 (IH, d).
58%
Stage #1: With hydrogenchloride; sodium nitrite In water at 5℃; for 0.25 h;
Stage #2: With sulfur dioxide; copper(l) chloride In water at 0 - 5℃; for 0.5 h;
Reference Example 31 6-chloropyridin-3-ylsulfonyl chloride; Under ice-cooling, thionyl chloride (12 mL) was added dropwise over 1 hr to water (70 mL) and the mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Separately, under ice-cooling, 5-amino-2-chloropyridine (5.0 g) was added to concentrated hydrochloric acid (40 mL) and the mixture was stirred. An aqueous solution (12.5 mL) of sodium nitrite (2.88 g) was added dropwise while keeping the inside temperature at not higher than 5° C., and the mixture was further stirred for 15 min. The reaction mixture was gradually added at 5° C. to the above-mentioned sulfur dioxide-containing solution added with cuprous chloride (70 mg). Under ice-cooling, the mixture was further stirred for 30 min. The precipitate was collected by filtration, and washed with water and ethanol to give the title compound (yield 4.79 g, 58percent). 1H-NMR (CDCl3) δ: 7.60-7.63 (1H, m), 8.24-8.27 (1H, m), 9.03-9.04 (1H, m).
58%
Stage #1: With hydrogenchloride; sodium nitrite In water at 5℃;
Stage #2: With thionyl chloride; copper(l) chloride In water for 0.5 h; Cooling with ice
Reference Example 134
6-Chloropyridin-3-ylsulfonyl chloride
Under ice-cooling, thionyl chloride (12 mL) was added dropwise over 1 hr to water (70 mL) and the mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution.
Under ice-cooling, 5-amino-2-chloropyridine (5.0 g) was added to concentrated hydrochloric acid (40 mL) and the mixture was stirred.
An aqueous solution (12.5 mL) of sodium nitrite (2.88 g) was added dropwise while keeping the inside temperature at not higher than 5°C, and the mixture was further stirred for 15 min.
The reaction mixture was gradually added at 5°C to the above-mentioned sulfur dioxide-containing solution added with cuprous chloride (70 mg).
Under ice-cooling, the mixture was further stirred for 30 min.
The precipitate was collected by filtration, and washed with water and ethanol to give the title compound (yield 4.79 g, 58percent).
1H-NMR (CDCl3)δ: 7.60-7.63 (1H, m), 8.24-8.27 (1H, m), 9.03-9.04 (1H, m).
26 g With hydrogenchloride; thionyl chloride; copper(l) chloride; sodium nitrite In water at -5 - 7℃; Thionyl chloride (60 mL, 823 mmol) was added to water (360 mL) at 0° C. over 60 min so that the temperature was maintained between 0 and 7° C.
After stirring the mixture for 17 hrs at 15° C., CuCl (0.218 g, 1.9 mmol) was added and the resulting solution cooled to 0° C. In a separate flask, a solution of 6-chloro-3-amino pyridine (25 g, 195 mmol) in con HCl (195 mL) was cooled to -5° C. and treated dropwise with a solution of sodium nitrite (14.4 g, 208 mmol) in water (58 mL) while the temperature was maintained between -5 and 0° C.
When the addition was complete, this solution was then added to the precooled solution of thionyl chloride in water at 0° C. and stirred for 1 hr.
The solid was collected by filtration, washed with water, and dried to yield 6-chloropyridine-3-sulfonyl chloride (26.0 g); 1H NMR (DMSO) δ: 7.48-7.50 (d, J=9.2 Hz, 1H), 7.96-7.98 (m, 1H), 8.55-8.56 (d, J=3.2 Hz, 1H).

Reference: [1] Patent: US2008/39464, 2008, A1, . Location in patent: Page/Page column 30-31
[2] Organic Process Research and Development, 2009, vol. 13, # 5, p. 875 - 879
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3947 - 3953
[4] Patent: WO2009/39328, 2009, A1, . Location in patent: Page/Page column 54
[5] Patent: EP1144368, 2004, B1, . Location in patent: Page 64
[6] Patent: WO2008/49605, 2008, A1, . Location in patent: Page/Page column 15
[7] Patent: WO2008/138594, 2008, A1, . Location in patent: Page/Page column 16
[8] Patent: US2007/60623, 2007, A1, . Location in patent: Page/Page column 24
[9] Patent: WO2006/36024, 2006, A1, . Location in patent: Page/Page column 161
[10] Patent: EP2336107, 2015, B1, . Location in patent: Paragraph 0308
[11] Patent: EP1803709, 2007, A1,
[12] Patent: WO2004/48367, 2004, A1, . Location in patent: Page 11
[13] Patent: WO2015/187088, 2015, A1, . Location in patent: Page/Page column 124
[14] Patent: US2016/96835, 2016, A1, . Location in patent: Paragraph 0075; 0076; 0162
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YieldReaction ConditionsOperation in experiment
62% With thionyl chloride In hydrogenchloride; water; ethyl acetate Example 131
2-[(6-But-2-Ynyloxy-Pyridine-3-Sulfonyl)-Methyl-Amino]-N-Hydroxy-Acetamide
In a 250 mL three neck round bottom flask equipped with an overhead stirrer was charged 27 mL water, and cooled to -3° C. (ice/NaCl).
Thionyl chloride (4.52 mL, 61.96 mmol, 4.5 eq) was added slowly so the temperature did not exceed 7° C.
The ice bath was removed, allowed to warm to room temperature, then 0.07 g (0.69 mmol, 0.05 eq) of copper (I) chloride was added.
The mixture was then recooled to -5°
5-Amino-2-chloropyridine (1.77 g, 13.67 mmol) was dissolved in 14 mL of concentrated HCl and cooled to -5° C. to which a solution of 1.04 g (15.14 mmol, 1.1 eq) NaNO2 in 12 mL of water was added slowly so the temperature was maintained between -5 and 0° C.
This mixture was then added to the thionyl chloride/water/CuCl mixture.
A frothing precipitate resulted and was allowed to stir for another 30 min.
The product was filtered and air dried.
Solids were taken up in ethyl acetate, washed with brine, dried over MgSO4 and concentrated in vacuo to afford 1.7 g (62percent) of 6-chloro-pyridine-3-sulfonyl chloride as a light tan solid.
Electrospray Mass Spec 210.9 (M+H)+
Reference: [1] Patent: US6225311, 2001, B1,
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  • [ 6684-39-5 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 387,389
[2] Helvetica Chimica Acta, 1939, vol. 21, p. 1746,1750
[3] DRP/DRBP Org.Chem.,
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  • [ 6684-39-5 ]
Reference: [1] Synlett, 2011, # 8, p. 1117 - 1120
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  • [ 6684-46-4 ]
  • [ 6684-39-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1931, vol. 487, p. 105,115
[2] Helvetica Chimica Acta, 1939, vol. 21, p. 1746,1750
[3] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 16, p. 2097 - 2100
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