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[ CAS No. 703-12-8 ] {[proInfo.proName]}

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Chemical Structure| 703-12-8
Chemical Structure| 703-12-8
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Product Details of [ 703-12-8 ]

CAS No. :703-12-8 MDL No. :MFCD00993162
Formula : C7H8BrNO2S Boiling Point : -
Linear Structure Formula :- InChI Key :ZAHMEHGOFNLRQN-UHFFFAOYSA-N
M.W : 250.11 Pubchem ID :101215
Synonyms :

Calculated chemistry of [ 703-12-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.04
TPSA : 54.55 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) : -6.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 1.36
Log Po/w (WLOGP) : 2.44
Log Po/w (MLOGP) : 1.4
Log Po/w (SILICOS-IT) : 1.03
Consensus Log Po/w : 1.57

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.49
Solubility : 0.818 mg/ml ; 0.00327 mol/l
Class : Soluble
Log S (Ali) : -2.11
Solubility : 1.95 mg/ml ; 0.0078 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.62
Solubility : 0.0601 mg/ml ; 0.00024 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.05

Safety of [ 703-12-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 703-12-8 ]

* 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 [ 703-12-8 ]
  • Downstream synthetic route of [ 703-12-8 ]

[ 703-12-8 ] Synthesis Path-Upstream   1~8

  • 1
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YieldReaction ConditionsOperation in experiment
89.74% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16 h; To a stirred solution of Methyl amine hydrochloride salt (0.13 g, 1.97 mmol) in DCM, DIPEA (0.52 mL, 2.95 mmol) and 4-bromobenzene-1-sulfonyl chloride (0.25 g, 0.98 mmol) were added and reaction allowed to stir at RT for 16 h. Progress of reaction was monitored by TLC. On completion, reaction mixture was quenched with water and extracted with DCM. The organic layer was dried on sodium sulfate and concentrated under reduced pressure to 1-bromo-4-(methylaminosulfonyl)benzene(0.220 g, 89.74percent) as yellow semisolid. (0432) MS: 248.0 [M−1].
0.8 g With triethylamine In dichloromethane at 20℃; for 2 h; Inert atmosphere In a 100-mL round-bottomed flask, 4-bromobenzenesulfonyl chloride (1 g, 4 mmol, Sigma-Aldrich, India) was dissolved in DCM (10 mL) at rt under nitrogen atmosphere. Triethylamine (1.7 mL, 7.8 mmol, SD Fine-Chem, India) and methylamine hydrochloride (350 mg, 5.46 mmol, Sigma-Aldrich, India) were added sequentially to the above solution at rt under nitrogen atmosphere. The reaction mixture was stirred at rt under nitrogen atmosphere for 2 h. The reaction mixture was diluted with ice-cold water (10 mL) and DCM (20 mL). The organic layer was separated, washed with water and brine, dried over anhydrous Na2S04 and filtered. The filtrate was concentrated under reduced pressure to give 4- bromo-N-methylbenzenesulfonamide (0.8 g) as a white solid.
Reference: [1] Patent: US2017/291910, 2017, A1, . Location in patent: Paragraph 0430-0432
[2] Journal of the American Chemical Society, 1923, vol. 45, p. 2697
[3] Patent: WO2014/35872, 2014, A1, . Location in patent: Page/Page column 136-137
  • 2
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YieldReaction ConditionsOperation in experiment
94% at 20℃; for 0.0833333 h; Example 13: 5-(4-[(Methylamino)sulfonyliphenyl)-2-(2-phenylethyl) pentanoic acida) Synthesis of 4-Bromo-λ/-methylbenzenesulfonamide. MeNH2 (7.5 ml, 8 M solution in EtOH, 60 mmol) was added to a solution of 4- bromobenzenesulfonyl chloride (5.0 g, 19.568 mmol) in THF (120 ml). The reaction mixture was stirred at room temperature for 5 min, poured into NH4CI (saturated aqueous solution, 300 ml) and extracted with EtOAc (500 ml). The <n="32"/>organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated, to furnish 4-bromo-W-methylbenzenesulfonamide, which was submitted to next step without further purification (4.60 g, white solid, yield: 94percent). 1H NMR (CDCI3, 250 MHz) δ ppm: 7.70 (m, 4H), 4.49 (bs, 1 H), 2.67 (d, J = 5.2 Hz, 3H).
94% at 0 - 20℃; for 2 h; Inert atmosphere To a stirred solution of 4-bromobenzene-l-sulfony chloride (BY; 2.5 g, 9.78 mmol) in CH2CI2 (20 mL) under inert atmosphere was added 2M methylamine in THF (10 mL, 19.56 mmol) at 0 °C. The reaction was then warmed to RT and stirred for 2 h. After complete consumption of the starting material, the volatiles were evaporated under reduced pressure. The residue was neutralized with saturated sodium bicarbonate solution (30 mL) and the compound was extracted with CH2CI2 (3x25 mL). The combined organic extracts were washed with water (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The crude was triturated with diethyl ether/pentane (3x15 mL) to afford BZ (2 g, 94percent) as a white solid. *H NMR (500 MHz, DMSO-i: δ 7.83 (d, J = 8.5 Hz, 2H), 7.70 (d, J = 8.5 Hz, 2H), 7.54 (s, 1H), 2.41 (d, / = 13.5 Hz, 3H). MS (ESI): m/z 250 [M+l]+
92% at 0 - 20℃; for 18 h; To a solution of 4-bromobenzene-1-sulfonyl chloride (3 g, 11.74 mmol) in DCM (20 mL) at 0°C was added methylamine (29 mL of a 2M solution in THF, 58.7 mmol) and the reaction mixture and stirred at room temperature for 18 hours. The reaction mixture was diluted with DCM (100 mL) and washed with ammonium chloride solution (20 mL). The organic layer was collected and dried overmagnesium sulfate, filtered and concentrated in vacuo. The resulting emulsion was purified by silica gel chromatography eluting with 0-40percent Heptane: ethyl acetate to yield the desired compound as a white solid (2.7 g, 92percent yield). ‘H NMR (250 MHz, DMSO-d6) 7.91 — 7.79 (m, 2H), 7.79 — 7.65 (m, 2H), 7.56 (s, 1H), 2.43 (s, 3H).
82% at 20℃; for 1 h; To synthesize compound 67, to a solution of 4-bromosulfonyl chloride (5.0 g, 20 mmol) in DCM (30 mL) was added methyl amine (2 M in THF, 20 mL, 40 mmol). The mixture was stirred at room temperature for 1 h and then the solvent was removed. A saturated NaHCO3 solution was added to the residue and then extracted with EtOAc. The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue triturated in hexane. Compound 67 was obtained as a white solid after filtration (4.0 g, 82percent). 1H NMR (DMSO-d6): δ 2.41 (d, J=5.0 Hz, 3H), 7.56 (q, J=4.9 Hz, 1H), 7.70 (d, J=8.7 Hz, 2H), 7.83 (d, J=8.7 Hz, 2H).
28% for 16 h; Sealed tube 4-Bromobenzene sulfonyl chloride (0.40 g, 1.56 mmol) and methylamine (10 mL, 33percent in ethanol) were stirred in a sealed tube for 16 hours.
The reaction mixture was concentrated in vacuo onto the Celite.(R). reagent.
The crude product was purified via Isco chromatography (the Redisep.(TM). column, silica, gradient 0-3percent ethyl acetate-dichloromethane) to provide 4-bromo-N-methylbenzenesulfonamide (0.11 g, 28percent). MS (ESI) m/z 250.
High performance liquid chromatography (HPLC) purity 100.0percent at 210-370 nm, 7.4 min.; the Xterra.(R). RP18 column, 3.5μ, 150*4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/Acetonitrile (ACN)+MeOH) for 10 min., hold 4 min.
1.80 g With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 0℃; for 0.166667 h; To a stirring solution of 4-bromobenzenesulfonyl chloride (2.0 g, 7.8 mmol, Sigma-Aldrich, St. Louis, MO) and DIEA (1.50 mL, 8.61 mmol) in CH2C12 (25 mL) at 0 °C, was added methanamine (2 M in THF, 7.83 mL, 15.7 mmol, Sigma-Aldrich, St. Louis, MO). After 10 min, the reaction mixture was treated with 1 M KH2P04 (50 mL). The organic was concentrated under reduced pressure and then purified by silica gel chromatography (0 to 4percent of MeOH/CH2Cl2) to afford 4-bromo-N-methylbenzenesulfonamide (1.80 g) as a white solid.

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 3880 - 3885
[2] Patent: WO2009/80722, 2009, A2, . Location in patent: Page/Page column 30-31
[3] Patent: WO2014/117090, 2014, A1, . Location in patent: Page/Page column 130
[4] Patent: WO2017/70081, 2017, A1, . Location in patent: Page/Page column 190
[5] Chemistry - A European Journal, 2017, vol. 23, # 57, p. 14345 - 14357
[6] Patent: US2005/245524, 2005, A1, . Location in patent: Page/Page column 80
[7] Patent: US2008/221201, 2008, A1, . Location in patent: Page/Page column 8
[8] Patent: WO2004/63179, 2004, A1, . Location in patent: Page 93
[9] Patent: WO2007/56341, 2007, A1, . Location in patent: Page/Page column 158
[10] Patent: US2008/9524, 2008, A1, . Location in patent: Page/Page column 390
[11] Journal of Organic Chemistry, 2008, vol. 73, # 6, p. 2428 - 2431
[12] Patent: WO2008/82487, 2008, A2, . Location in patent: Page/Page column 115
[13] Organic Letters, 2011, vol. 13, # 6, p. 1556 - 1559
[14] Patent: WO2011/48082, 2011, A1, . Location in patent: Page/Page column 85
[15] Patent: WO2014/35872, 2014, A1, . Location in patent: Page/Page column 134
[16] Journal of Medicinal Chemistry, 2014, vol. 57, # 7, p. 3094 - 3116
[17] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 1160
[18] Organic Letters, 2016, vol. 18, # 9, p. 2280 - 2283
[19] Patent: EP1798229, 2007, A1, . Location in patent: Page/Page column 108
[20] Organic Letters, 2017, vol. 19, # 21, p. 5844 - 5847
[21] Chemical Communications, 2018, vol. 54, # 60, p. 8403 - 8406
  • 3
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Reference: [1] Patent: US5380721, 1995, A,
[2] Patent: US2011/98311, 2011, A1,
[3] Journal of Fluorine Chemistry, 2016, vol. 188, p. 65 - 75
[4] Journal of Fluorine Chemistry, 2016, vol. 188, p. 65 - 75
  • 4
  • [ 67-56-1 ]
  • [ 701-34-8 ]
  • [ 703-12-8 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 21, p. 5790 - 5793
[2] RSC Advances, 2012, vol. 2, # 23, p. 8645 - 8652
  • 5
  • [ 1158827-44-1 ]
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Reference: [1] Journal of Fluorine Chemistry, 2016, vol. 188, p. 65 - 75
[2] Journal of Fluorine Chemistry, 2016, vol. 188, p. 65 - 75
  • 6
  • [ 106-53-6 ]
  • [ 703-12-8 ]
Reference: [1] Patent: US2017/291910, 2017, A1,
  • 7
  • [ 42111-84-2 ]
  • [ 74-88-4 ]
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Reference: [1] Synthetic Communications, 1989, vol. 19, # 9-10, p. 1499 - 1504
  • 8
  • [ 86674-11-5 ]
  • [ 67-56-1 ]
  • [ 138-36-3 ]
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Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 4, p. 671 - 675[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 4, p. 761 - 766
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