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Chemical Structure| 6292-59-7
Chemical Structure| 6292-59-7
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Product Details of [ 6292-59-7 ]

CAS No. :6292-59-7 MDL No. :MFCD00068599
Formula : C10H15NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :KYDZEZNYRFJCSA-UHFFFAOYSA-N
M.W : 213.30 Pubchem ID :222872
Synonyms :

Calculated chemistry of [ 6292-59-7 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.71
TPSA : 68.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.4
Log Po/w (XLOGP3) : 2.13
Log Po/w (WLOGP) : 2.71
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 1.11
Consensus Log Po/w : 1.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.69
Solubility : 0.436 mg/ml ; 0.00204 mol/l
Class : Soluble
Log S (Ali) : -3.2
Solubility : 0.134 mg/ml ; 0.00063 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.18
Solubility : 0.141 mg/ml ; 0.000659 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 6292-59-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6292-59-7 ]

* 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 [ 6292-59-7 ]
  • Downstream synthetic route of [ 6292-59-7 ]

[ 6292-59-7 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 15084-51-2 ]
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YieldReaction ConditionsOperation in experiment
75% With ammonia In dichloromethane; water at 0 - 20℃; for 20 h; [0362] To a 500-mL round-bottomed flask was added (4-tert-butylphenyl) sulfonyl chloride (2.30 g, 10.0 mmol) in 100 mL CH2Cl2 at 0° C. and then concentrated NH4OH (50 mL, 100 mmol, 10 equiv). The mixture was allowed to warm to rt and stirred for 20 h. The solvent was evaporated under diminished pressure and the remaining slurry was filtered by Buechner funnel, giving 1.60 g (75percent) of Compound A as a white solid.
Reference: [1] Chemische Berichte, 1993, vol. 126, # 7, p. 1713 - 1722
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 21, p. 3355 - 3368
[3] Patent: US2004/39033, 2004, A1, . Location in patent: Page/Page column 16; 64
[4] European Journal of Medicinal Chemistry, 2004, vol. 39, # 10, p. 835 - 847
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 16, p. 4397 - 4406
[6] Tetrahedron, 2014, vol. 70, # 48, p. 9224 - 9229
[7] Molecules, 2018, vol. 23, # 7,
[8] Inorganica Chimica Acta, 2019, p. 724 - 732
  • 2
  • [ 2396-68-1 ]
  • [ 6292-59-7 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 9, p. 2599 - 2602
  • 3
  • [ 5636-16-8 ]
  • [ 6292-59-7 ]
Reference: [1] Synlett, 2004, # 11, p. 1901 - 1904
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  • [ 701-34-8 ]
  • [ 6292-59-7 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 29, p. 9847 - 9850
  • 5
  • [ 253185-03-4 ]
  • [ 6292-59-7 ]
Reference: [1] Molecules, 2018, vol. 23, # 7,
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  • [ 6292-59-7 ]
  • [ 150728-13-5 ]
  • [ 150727-06-3 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In dimethyl sulfoxide at 100 - 105℃; In a flask equipped with mechanical stirrer, thermometer, reflux condenser,dropping funnel and heating mantle, 4,6-dichloro-5-(2-methoxyphenoxy)-2,2'bipyrimidine1 (105 g), 4-(tert-butyl)benzenesulfonamide 2 (64.1 g, 0.30 mol) inDMSO (525 mL) are placed. To this suspension potassium carbonate (83 g, 0.60 mol) is5 added. The resulting mixture is heated at 100 - 1 05°C for 3 - 4 h upon stirring. Reactionprogress is monitored by HPLC. The solution is cooled down to 20 -25°C. Water (875mL) is added dropwise within 10 - 15 min. and stirring is continued for 1 h.Precipitated solid is filtered off, washed with water (2 x 350 mL), then transferred intoflask. After addition of water (800 mL) and concentrated hydrochloric acid (50 mL) the10 solution is stirred for 30 min. The precipitated solid is filtered off, washed with water (2x 200 mL) and acetone (2 x 175 mL). The solid is dried at 40 ± 2°C for 16-24 h underatmospheric pressure. The product is obtained in 157.8- 158.7 g (100percent) yield as creamcoloredsolid.
96% With potassium carbonate In dimethyl sulfoxide at 95 - 100℃; for 4 h; A mixture of 4,6-dichloro-5-(2-methylphenoxy)-2,2'- bipyrimidine(II) (100.0 g) is reacted with 4-tert-butylbenzene sulfonamide (III) (61.0 g) in the presence of Potassium carbonate (118.7 g) in dimethyl sulfoxide (300 ml) was heated at 95° to 100°C for about 4 hours till the completion of the reaction. The reaction mixture is cooled at 30° to 40°C, diluted with water (800 ml) and stirred for 30 min. The reaction mixture was filtered and washed twice with water (100 ml x 2). To this wet solid compound, dilute hydrochloric acid (50 ml in 500 ml water) (50.0 ml) is added at 25° to 35°C and stirred for 1.0 hour. The solid compound was filtered, washed with water (100ml x 3) and dried at 70 to 75°C under vacuum for 8 to 10 hours to give crude 4-tert butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)pyrimidine-4-yl) benzenesulfonamide (IV) (145.0 g)[104] Purity by HPLC: 98.0percent[105] Yield: 96.0percent
96%
Stage #1: With potassium carbonate In dimethyl sulfoxide for 0.5 h; Inert atmosphere
Stage #2: at 120℃; for 2 h;
Example 3: Preparation of 4-tert-Butyl-N-[6-chloro5-(2-methoxyphenoxy) [2,2]- bipyrimidinyl-4-yl] -benzene sulfonamide compound of formula-4.p-t-butyl benzene sulphonamide (2.2g,0.0104mol) was taken in Dimethyl Sulphoxide and potassium carbonate was added (2.75g,0.0198mol) under inter atmosphere and stirred for 0.5h. 3.4g of 4,6- dichloro 5-(2-methoxyphenoxy) [2,2]-bipyrimidinyl compound (formula-3) 3.44g, 0.009mol was added and heated to 120°C and maintained at the same temperature for 2h. The reaction mass was quenched in IN hydrochloric acid and stirred for 2h. Product precipitates out and was filtered and washed with water and dried under vacuum yielding 4.3g(96percent) of pale yellow crystalline solid 4,6- dichloro 5-(2-methoxyphenoxy) [2,2]- bipyrimidinyl compound of formula-3 having the X-ray diffraction pattern with peaks at 8.547, 9.867, 11.068, 11.97, 13.851, 14.726, 15.539, 17.213, 18.428, 20.463, 22.232, 22.704, 23.536, 23.937, 24.827, 26.291, 26.545, 27.294, 27.815, 28.223, 29.278, 30.022, 30.5, 31.447, 31.996, 32.454, 33.43, 33.644, 34.251, 34.89, 35.662, 36.393, 37.402, 38.523, 39.022, 40.238, 40.724, 41.35, 41.93, 43.732, 44.289, 45.24, 47.267, 47.978, 49.123, 49.438, 50.22, ± 0.2 degrees two theta values.This was optionally purified using acetonitrile under the reflux condition to give pure pale yellow to off white crystalline product for formula-4 having the XRD.
96% With potassium carbonate In dimethyl sulfoxide at 120℃; for 2 h; Inert atmosphere p-t-butyl benzene sulphonamide (2.2 g, 0.0104 mol) was taken in Dimethyl Sulphoxide and potassium carbonate was added (2.75 g, 0.0198 mol) under inter atmosphere and stirred for 0.5 h. 3.4 g of 4,6- dichloro 5-(2-methoxyphenoxy) [2,2]-bipyrimidinyl compound (formula-3) 3.44 g, 0.009 mol was added and heated to 120° C. and maintained at the same temperature for 2 h. The reaction mass was quenched in iN hydrochloric acid and stirred for 2 h. Product precipitates out and was filtered and washed with water and dried under vacuum yielding 4.3 g (9 6percent) of pale yellow crystalline solid 4,6- dichioro 5-(2-methoxyphenoxy) [2,2]- bipyrimidinyl compound of formula-3 having the X-ray diffraction pattern with peaks at 8.547, 9.867, 11.068, 11.97, 13.851, 14.726, 15.539, 17.213, 18.428, 20.463, 22.232, 22.704, 23.536,23.937, 24.827, 26.291, 26.545, 27.294, 27.815, 28.223,29.278, 30.022, 30.5, 31.447, 31.996, 32.454, 33.43, 33.644,34.251, 34.89, 35.662, 36.393, 37.402, 38.523, 39.022,40.238, 40.724, 41.35, 41.93, 43.732, 44.289, 45.24, 47.267, 47.978,49.123,49.438, 50.22, ±0.2 degrees two theta values.
93%
Stage #2: at 90℃; for 3 h;
A solution of p-tert-butylbenzenesulfonamide (VI) (13.5 g, 63 mmol) was dissolved in sodium hydroxide solution (31.5 mL, 2N) and the solvent was distilled off under reduced pressure to give the sodium salt of p-tert-butylbenzenesulfonamide.A solution of tert-butylbenzenesulfonamide sodium and 4,6-dichloro-5- (2-methoxyphenoxy) -2,2 '-bipyridine (V) (21.05 g, 60.3 mmol) (200 mL) and heated to 90 ° C with stirring for 3 h. TLC was complete. The residue was diluted with IN hydrochloric acid and the pH was adjusted to 3 to 4 with IN hydrochloric acid. The crystals were recrystallized and dried under reduced pressure to give 29.5 g of a white solid as N- [6-chloro (2-methoxyphenoxy) [2,2 '] - dipyridyl] -4-yl] -4- (1,1-dimethylethyl) -benzenesulfonamide (W) The yield was 93percent.
92%
Stage #1: With potassium carbonate In 4-methyl-2-pentanone for 5 h; Inert atmosphere; Reflux
Stage #2: With hydrogenchloride In water; 4-methyl-2-pentanone at 50℃;
44g (0.21 moles) of 4-tert-butyl-benzenesulfonamide, 72g (0.21 moles) of 4,6- dichloro-5-(2-methoxy-phenoxy)-[2,2']bipyrimidine and 0.7g of tetrabutylammonium bromide are added to a suspension of 35g (0.25 moles) of potassium carbonate in 720 ml of methyl isobutyl ketone (MIBK), kept in an inert atmosphere (nitrogen). Once the addition is complete, the suspension is heated to reflux, operating so as to azeotropically remove the water that forms during the reaction. The reaction is kept at reflux for 5 hours. Once the reaction is complete, the suspension is cooled to 5O0C and diluted with 0.2 litres of water. Hydrochloric acid 35percent is then added until obtaining a pH between 2.0 and 3.0. The suspension is cooled to 5°C / 100C and the product is left to crystallise for 10 hours. The suspension is filtered and 120 g in wet form of the title compound are obtained equal to 100 g in dry form (0.19 moles) (yield 92percent; purity 99.6percent HPLC).
92% With tetrabutylammomium bromide; potassium carbonate In water; 4-methyl-2-pentanone for 5 h; Inert atmosphere; Reflux EXAMPLE 1
Preparation of the Compound of Formula (II) 4-Tert-Butyl-N-[6-Chloro-5-(2-Methoxy-Phenoxy)-[2,2']Bipyrimidinyl-4-yl]-Benzenesulfonamide
44 g (0.21 moles) of 4-tert-butyl-benzenesulfonamide, 72 g (0.21 moles) of 4,6-dichloro-5-(2-methoxy-phenoxy) -[2,2']bipyrimidine and 0.7 g of tetrabutylammonium bromide are added to a suspension of 35 g (0.25 moles) of potassium carbonate in 720 ml of methyl isobutyl ketone (MIBK), kept in an inert atmosphere (nitrogen).
Once the addition is complete, the suspension is heated to reflux, operating so as to azeotropically remove the water that forms during the reaction.
The reaction is kept at reflux for 5 hours.
Once the reaction is complete, the suspension is cooled to 50° C. and diluted with 0.2 litres of water.
Hydrochloric acid 35percent is then added until obtaining a pH between 2.0 and 3.0.
The suspension is cooled to 5° C./10° C. and the product is left to crystallise for 10 hours.
The suspension is filtered and 120 g in wet form of the title compound are obtained equal to 100 g in dry form (0.19 moles) (yield 92percent; purity 99.6percent HPLC).
75% With potassium carbonate In dimethyl sulfoxide at 120℃; Example 7: p-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy) [2,2'-bipyrimidin]-4-yl] benzene sulfonamide formula Via.The compound of formula VII (500g, 1.0eq), 4-tert butyl benzene sulfonamide (305.2g, 1.0eq) and potassium carbonate (237.24g, 1.2eq) was heated in dimethylsulfoxide (2500.0ml, 5.0vol) at 120°C for 10-12 hours. After completion of reaction, the reaction mixture was cooled to 20°C-25°C and filtered. Filtrate was added to a mixture of water (6000.0ml, 12.0vol) and concentrated hydrochloric acid (100ml, 0.2vol) at 5°C-10°C. After completion of addition the reaction mixture was maintained at 5°C-10°C for 1 hour. Precipitated solid was filtered and washed with water (5000ml, 10.0vol). Dried the solid at 55°C-60°C for 20Hrs under vacuum to get title compound (Yield: 742.0g, 98.67percent, HPLC purity 87.39).The dried solid (742.0g, 1eq) was heated in ethyl acetate (7420.0ml, 10.0vol) at 75°C-80°C for 1 hour. Cooled to 5-10°C and filtered. Washed with ethyl acetate (371.0ml, 0.5vol) and dried the solid under vacuum at 55-60°C for 15hrs.Yield : 556.5g (75percent, HPLC purity 99percent).
75.1%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25 h; Inert atmosphere
Stage #2: at 50℃; for 16 h;
General procedure: Sulfonamide 10a (2.0 g, 6.2 mmol, 1.1 eq) was solvedin dry THF (8 ml) and cooled to 78 °C under a nitrogen atmosphere.n-BuLi (1.62 N solution in hexane, 7.70 ml, 2.2 eq) wasadded drop-wise. After the addition was completed, the solutionwas stirred for 15 min, then the temperaturewas allowed to raise at60 °C and the THF was evaporated under very high vacuum. DMFwas added (10 ml), followed by dichloropyrimidine intermediate 9(2.0 g, 5.7 mmol, 1.0 eq) and the mixture was stirred overnight at50 °C. The reaction mixture was poured onto a 1:1 mixture ofwater-ice and the aqueous phase was washed with DEE, thenacidified with HCl and the resulting precipitate was filtrated off,washed with water and dried at 110 °C to afford a bright yellowsolid (2.22 g, yield 61.2percent).
49.51 kg With tetrabutylammomium bromide; potassium carbonate In water; toluene for 5 h; Dean-Stark; Large scale Bipyrimidinedione (3, 30 kg, 96.07 mol) was added to phosphorous oxychloride(58.8 kg, 384.50 mol) and the reaction mixture was heated to 103–105C and stirred for4 h. It was diluted with toluene (45 L), added to a mixture of toluene (315 L) and water(105 L) at 20–50C and then treated with 30percent w/w aqueous sodium hydroxide solution(82.5 L) at 70–80C. The two layers were separated, and the organic layer was washedwith 0.4percent w/v aqueous sodium hydroxide solution (120 L) at 70–80C. 4-(1,1-Dimethylethyl)benzene sulfonamide (5, 20.49 kg, 96.06 mol) was added to the organic layer at50C followed by potassium carbonate (15.9 kg, 115.21 mol) and tetra(n-butyl)ammoniumbromide (0.96 kg, 2.98 mol). Then it was heated to reflux and the water generatedwas separated azeotropically using a Dean-Stark trap for 5 h. The reaction mixture was cooled to 20–25C and the wet product was collected, added to de-mineralized water(360 L) and heated to 50–60C. Then, the toluene was distilled off under reduced pressureat 60C and the residue was acidified with conc. hydrochloric acid (18 kg, 35percent w/w)over 40 min at 25C and stirred for 2 h at 20–30C. Then the precipitated solid was collected,washed with de-mineralized water (60 L) and dried at 60C to provide compound6 as colorless crystals (49.51 kg, 98percent, and purity of 99.05percent a/a), mp. 229–230C, MS(ESI): m/z 524.2.0 [(MCH)]; 1H NMR (DMSO, 300 MHz): d 1.27 (s, 9H), 3.72 (s, 3H),6.77 (d, 1H), 6.85 (dd, 1H), 7.11 (m, 2H), 7.57 (d, 2H), 7.73 (dd, 1H), 8.28 (brs, 2H), 9.13(d, 2H), 12.09 (brs, 1H).

Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 6, p. 1382 - 1387
[2] Patent: WO2014/104904, 2014, A1, . Location in patent: Page/Page column 13; 14
[3] Organic Process Research and Development, 2013, vol. 17, # 8, p. 1021 - 1026
[4] Patent: WO2012/73135, 2012, A1, . Location in patent: Page/Page column 10
[5] Patent: WO2013/57545, 2013, A1, . Location in patent: Paragraph 15
[6] Patent: US2014/275535, 2014, A1, . Location in patent: Paragraph 0077;
[7] Patent: CN104193687, 2017, B, . Location in patent: Paragraph 0135-0137
[8] Patent: WO2010/103362, 2010, A2, . Location in patent: Page/Page column 5; 6
[9] Patent: US2012/41200, 2012, A1, . Location in patent: Page/Page column 2
[10] Patent: WO2012/56468, 2012, A1, . Location in patent: Page/Page column 16
[11] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 658 - 670
[12] Patent: US2008/242687, 2008, A1, . Location in patent: Page/Page column 32-33; 34
[13] Patent: WO2009/95933, 2009, A2, . Location in patent: Page/Page column 18; 22
[14] Patent: US2010/256371, 2010, A1, . Location in patent: Page/Page column 12
[15] Patent: WO2011/24056, 2011, A2, . Location in patent: Page/Page column 20
[16] Patent: WO2011/21216, 2011, A2, . Location in patent: Page/Page column 19-20
[17] Organic Preparations and Procedures International, 2013, vol. 45, # 6, p. 510 - 514
[18] Organic Preparations and Procedures International, 2016, vol. 48, # 6, p. 481 - 491
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YieldReaction ConditionsOperation in experiment
97%
Stage #1: With potassium carbonate In toluene at 50℃; for 0.5 h; Large scale
Stage #2: at 110℃; for 10 h; Large scale
A mixture of 4-tet-butyl benzene sulfonamide 6 (0.85 Kg, 4.0 mol), toluene (2.8 L) and potassium carbonate (1.1 Kg, 8.0 mol) was heated to50°C for 30 min. To the reaction mixture was added 5 (1.4 Kg, 4.0 mol) followed by heating to 110°C for 10 h. The reaction mixture was cooledto 25°C, water (28 L) was added and pH was adjusted to below 3 by using 5N hydrochloric acid and stirred for 30 mins. The precipitated solidwas filtered, washed with water (4.8 L) and dried in oven at 60°C for 6 h to afford 7 (2.05 Kg, 97percent). m.p 214-216 οC. 1H-NMR (300MHz,CDCl3): δ 1.21 (9H, s), 3.72 (3H, s), 6.54-6.55 (1H, d), 6.72-6.76 (1H, t), 6.86-6.98 (2H, m), 7.23-7.25 (2H, d), 7.43-7.49 (3H, m), 8.97-8.98(2H, d); MS: m/z 526.3 (M+H); IR (KBr) (υmax, Cm-1): 3466.7 (-NH stretching), 1592.9 (C=O stretching).
Reference: [1] Synlett, 2014, vol. 25, # 2, p. 265 - 269
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Reference: [1] Patent: WO2013/186706, 2013, A1, . Location in patent: Page/Page column 8
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