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[ CAS No. 4518-10-9 ] {[proInfo.proName]}

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Product Details of [ 4518-10-9 ]

CAS No. :4518-10-9 MDL No. :MFCD00017102
Formula : C8H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VZDNXXPBYLGWOS-UHFFFAOYSA-N
M.W : 151.16 Pubchem ID :78274
Synonyms :

Calculated chemistry of [ 4518-10-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.13
TPSA : 52.32 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) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 1.54
Log Po/w (WLOGP) : 1.06
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 0.97
Consensus Log Po/w : 1.29

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.02
Solubility : 1.45 mg/ml ; 0.00957 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 0.854 mg/ml ; 0.00565 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.1
Solubility : 1.21 mg/ml ; 0.008 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.11

Safety of [ 4518-10-9 ]

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 [ 4518-10-9 ]

* 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 [ 4518-10-9 ]
  • Downstream synthetic route of [ 4518-10-9 ]

[ 4518-10-9 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 4518-10-9 ]
  • [ 618-91-7 ]
Reference: [1] RSC Advances, 2017, vol. 7, # 86, p. 54881 - 54891
[2] Annales Academiae Scientiarum Fennicae, Series A, 1942, vol. 59, # 9, p. 1,4
[3] Yakugaku Zasshi, 1938, vol. 60, p. 515,520[4] Chemische Berichte, 1940, vol. 73, p. 867,873
  • 2
  • [ 4518-10-9 ]
  • [ 98-09-9 ]
  • [ 107922-46-3 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 16 h; Inert atmosphere; Cooling with ice Methyl 3-aminobenzoate (10 g, 66.2 mmol) was dissolved in pyridine (100 mL) and cooled in an ice bath for 15 min. Benzenesulfonyl chloride (8.53 ml, 66.2 mmol) was added via syringe over 5 min, and the solution then stirred with warming to room temperature over a 16 h period. The reaction mixture was poured onto ice and IM HCl (250 mL total volume) to afford a heterogenous acidic mixture (pH 2-3). The solid was filtered and washed with water. The collected solid was dried under hi-vacuum for 12 h to afford the coupled product (19.3, 100percent) as an off-white solid.
Reference: [1] Patent: WO2010/126922, 2010, A1, . Location in patent: Page/Page column 26
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 10, p. 3317 - 3327
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4436 - 4440
  • 3
  • [ 4518-10-9 ]
  • [ 107922-46-3 ]
YieldReaction ConditionsOperation in experiment
90% With 4-methyl-morpholine; benzenesulfonyl chloride In dichloromethane; ethyl acetate EXAMPLE 8
Preparation of Methyl 3-(Phenylsulfonyl)aminobenzoate (18) STR10
To 4.6 g (3.03 mmol) of the methyl 3-aminobenzoate prepared in Example 1 in 30 mL of methylene chloride containing 4.0 mL (36 mmol) of N-methylmorpholine was added 4.0 mL (33 mmol) of benzenesulfonyl chloride.
After stirring at room temperature for 1 hr the reaction mixture was quenched with water (100 mL).
The suspension was dissolved in ethyl acetate/ether combination.
The organic phase was washed sequentially with 2N HCl and then sodium bicarbonate.
The organic phase was dried (MgSO4), and concentrated and triturated from ethyl acetate/hexane ether to give 8.0 g (90percent) of the title compound as a colorless solid: NMR (DMSO-d6; 300 MHz) δ 10.58 (s, 1H), 7.75-7.84 (m, 3H), 7.52-7.72 (m, 4H), 7.35-7.45 (m, 2H), and 3.82 ppm (s, 3H).
Reference: [1] Patent: US5741819, 1998, A,
  • 4
  • [ 4518-10-9 ]
  • [ 6942-37-6 ]
  • [ 106896-48-4 ]
Reference: [1] Synthesis, 2009, # 8, p. 1305 - 1308
  • 5
  • [ 4518-10-9 ]
  • [ 6942-37-6 ]
  • [ 46064-79-3 ]
  • [ 106896-48-4 ]
Reference: [1] Synthesis, 2009, # 8, p. 1305 - 1308
  • 6
  • [ 4518-10-9 ]
  • [ 6942-37-6 ]
  • [ 46064-79-3 ]
  • [ 106896-48-4 ]
Reference: [1] Synthesis, 2009, # 8, p. 1305 - 1308
  • 7
  • [ 4518-10-9 ]
  • [ 63555-50-0 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With hydrogenchloride; acetic acid; sodium nitrite In water at -10 - -5℃; for 1.5 h;
Stage #2: With sulfur dioxide; copper(l) chloride In water; acetic acid at 5 - 15℃; for 1 h;
To a mixture of conc. HCl (16 mL) and glacial acetic acid (5 mL), was added methyl 3-aminobenzoate (7.40g, 49 mmol). The flask was placed in a dry ice-ethanol bath and the temperature of the mixture lowered to -10°C. A solution of sodium nitrite (3.7 g, 53 mmol) in water (5.4 mL) was added dropwise, at such a rate so that the temperature did not exceed -5°C. The mixture was left stirring at -10°C to -5°C for 1h 30 min. SO2 was introduced into acetic acid (49 mL) by a tube immersed below the surface, over a period of 30 min. CuCl (1.35 g, 13.6 mmol) was added and SO2 was kept bubbling for a further h. The mixture was cooled with ice to 5°C and the diazonium salt was added dropwise so as to maintain the temperature. After the addition the mixture was allowed to warm to 15°C and stirred for 1 h. Ice was added and the mixture stirred until it melted, extracted with ether (3 x 120 mL) washed with NaHCO3 (100 mL) dried (MgSO4) and the solvent evaporated in vacuo to give 31 (7.7 g, 67percent) as orange plates (mp 64-66°C).
42%
Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃;
Stage #2: With sulfur dioxide; acetic acid; copper(l) chloride In water at 20℃; for 3 h;
A mixture of METHYL-4-AMINOBENZOATE (1.0 g, 6.6 MMOL) in concentrated hydrochloric acid (15 mL) was maintained AT 0° C AS A SOLUTION of sodium nitrite (1.12 g, 13.2 mmol) in water (4 mL) was added dropwise with stirring. This reaction was maintained at 0° C for 30 minutes. In a separate flask, a mixture of copper (L) chloride (89 mg, 0.66 MMOL) and glacial acetic acid (9.9 mL) cooled to below room temperature was saturated with gaseous sulfur dioxide for several minutes. The mixture containing the crude diazonium salt was then added to the second flask portionwise with extreme caution. The mixture was allowed to stir at ambient temperature for 3h before being poured onto crushed ice. The resulting solid was filtered. Additional product was recovered by extraction of the aqueous filtrate with ethyl acetate. The combined yield of methyl 4- (CHLOROSULFONYL) benzoate is 0.65 g. (42percent).
Reference: [1] ChemSusChem, 2017, vol. 10, # 1, p. 151 - 155
[2] Tetrahedron, 2015, vol. 71, # 38, p. 6701 - 6719
[3] Patent: WO2004/48349, 2004, A1, . Location in patent: Page 67
  • 8
  • [ 4518-10-9 ]
  • [ 6942-37-6 ]
  • [ 106896-48-4 ]
Reference: [1] Synthesis, 2009, # 8, p. 1305 - 1308
  • 9
  • [ 4518-10-9 ]
  • [ 6942-37-6 ]
  • [ 46064-79-3 ]
  • [ 106896-48-4 ]
Reference: [1] Synthesis, 2009, # 8, p. 1305 - 1308
  • 10
  • [ 4518-10-9 ]
  • [ 111331-82-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 22, p. 10299 - 10314
  • 11
  • [ 4518-10-9 ]
  • [ 118684-31-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 39, p. 11981 - 11985[2] Angew. Chem., 2017, vol. 129, p. 12143 - 12147,5
  • 12
  • [ 4518-10-9 ]
  • [ 691-64-5 ]
  • [ 118684-31-4 ]
  • [ 176980-36-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 39, p. 11981 - 11985[2] Angew. Chem., 2017, vol. 129, p. 12143 - 12147,5
  • 13
  • [ 4518-10-9 ]
  • [ 13675-18-8 ]
  • [ 99769-19-4 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
  • 14
  • [ 4518-10-9 ]
  • [ 99769-19-4 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
  • 15
  • [ 4518-10-9 ]
  • [ 691-64-5 ]
  • [ 118684-31-4 ]
  • [ 176980-36-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 39, p. 11981 - 11985[2] Angew. Chem., 2017, vol. 129, p. 12143 - 12147,5
  • 16
  • [ 4518-10-9 ]
  • [ 72548-79-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 3, p. 331 - 341
  • 17
  • [ 4518-10-9 ]
  • [ 67-64-1 ]
  • [ 184150-96-7 ]
YieldReaction ConditionsOperation in experiment
83% With palladium diacetate; copper(II) acetate monohydrate In dimethyl sulfoxide at 80℃; for 48 h; Sealed tube; Inert atmosphere prepared a degass ed mixture of compound LVI (10.0 g, 0.061 mol) and copper(II) acetate 10 monohydrate (36.2 g, 0.182 mol) in dimethyls ulfoxide (50 mL). To the flask was added acetone (100 mL), followed by palladium(II) acetate (0.270 g, 0.001 mol), and the resulting reaction mixture was heated at 80 °C for 48 h. After cooling to room temperature, the reaction mixture was filtered through a pad of celite and the filtrate w as diluted with water (80 mL). The aqueous mixture w as extracted with ethyl acetate (3 x 100 mL) and the 148 of 363 {//-- DRAFT --//4069/3020WO/00228726/v2} 4069.3020 WO combined organic extracts were dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to obtain the crude product mixture, which was purified by silica gel chromatography using a gradient of 5-7percent ethyl acetate in hexanes as the eluant to affod LVII (4.8 g, 83percent) as a pale yellow solid.1H NMR (400 MHz, CDCl3) δ 8.26 (brs, 5 1H), 8.04 (s, 1H), 7.77 (dd, J= 8.3, 3.4 Hz, 1H), 7.50 (d, J= 8.3 Hz, 1H), 6.26 (s, 1H), 3.92 (s, 3H), 2.47 (s, 3H); MS (ESI, positive mode) m/z 190 (MH+).
Reference: [1] Patent: WO2015/73528, 2015, A1, . Location in patent: Page/Page column 148-149
  • 18
  • [ 4518-10-9 ]
  • [ 75-87-6 ]
  • [ 153072-43-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 9, p. 2236 - 2242
  • 19
  • [ 4518-10-9 ]
  • [ 209459-11-0 ]
Reference: [1] Patent: WO2009/104155, 2009, A1,
  • 20
  • [ 4518-10-9 ]
  • [ 677304-83-5 ]
Reference: [1] Patent: WO2009/104155, 2009, A1,
  • 21
  • [ 4518-10-9 ]
  • [ 1038509-28-2 ]
Reference: [1] Patent: WO2009/104155, 2009, A1,
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