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[ CAS No. 7143-01-3 ] {[proInfo.proName]}

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Chemical Structure| 7143-01-3
Chemical Structure| 7143-01-3
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Product Details of [ 7143-01-3 ]

CAS No. :7143-01-3 MDL No. :MFCD00007556
Formula : C2H6O5S2 Boiling Point : -
Linear Structure Formula :- InChI Key :IZDROVVXIHRYMH-UHFFFAOYSA-N
M.W : 174.20 Pubchem ID :81560
Synonyms :

Calculated chemistry of [ 7143-01-3 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 30.74
TPSA : 94.27 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.51
Log Po/w (XLOGP3) : -0.78
Log Po/w (WLOGP) : 1.08
Log Po/w (MLOGP) : -1.31
Log Po/w (SILICOS-IT) : -0.77
Consensus Log Po/w : -0.25

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.3
Solubility : 88.0 mg/ml ; 0.505 mol/l
Class : Very soluble
Log S (Ali) : -0.72
Solubility : 33.1 mg/ml ; 0.19 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.24
Solubility : 99.8 mg/ml ; 0.573 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.09

Safety of [ 7143-01-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7143-01-3 ]

* 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 [ 7143-01-3 ]
  • Downstream synthetic route of [ 7143-01-3 ]

[ 7143-01-3 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 64-17-5 ]
  • [ 7143-01-3 ]
  • [ 62-50-0 ]
Reference: [1] Chemische Berichte, 1905, vol. 38, p. 2018
[2] Chemische Berichte, 1905, vol. 38, p. 2018
  • 2
  • [ 110-63-4 ]
  • [ 7143-01-3 ]
  • [ 55-98-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1960, vol. 631, p. 180 - 184
  • 3
  • [ 462-06-6 ]
  • [ 7143-01-3 ]
  • [ 455-15-2 ]
  • [ 657-46-5 ]
  • [ 654-47-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2004, vol. 2, # 21, p. 3150 - 3154
  • 4
  • [ 99-92-3 ]
  • [ 7143-01-3 ]
  • [ 5317-89-5 ]
Reference: [1] Patent: US2003/153596, 2003, A1,
  • 5
  • [ 619-45-4 ]
  • [ 7143-01-3 ]
  • [ 7151-76-0 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 44, p. 6300 - 6303
  • 6
  • [ 115256-13-8 ]
  • [ 7143-01-3 ]
  • [ 115256-11-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1151 - 1155
  • 7
  • [ 85275-45-2 ]
  • [ 7143-01-3 ]
  • [ 129888-60-4 ]
YieldReaction ConditionsOperation in experiment
90% With dmap; triethylamine In tetrahydrofuran at 20℃; for 16 h; Example 138Reagents and conditions: (a) NaH, DMF, 100 C, 16 h. (b) TFA, DCM, rt 1 h. (c) C8H7O2NCI2, HBTU, DIEA, THF, 50 C 16 h.[0567] Synthesis of tert-butyl 3-((methylsulfonyl)oxy)piperidine-l-carboxylate: To the solution of tert-butyl 3-hydroxypiperidine-l-carboxylate (2.01 g, 10 mmol, 1.0 eq) in THF (30 mL) was added DMAP (122 mg, 1.0 mmol, 0.1 eq), TEA (2.8 mL, 20 mmol, 2.0 eq) and methanesulfonic anhydride (1.91 g, 11 mmol, 1.1 eq). The mixture was stirred at rt for 16 h, filtered off and concentrated in vacuo to afford a residue which purified by column chromatography (silica gel, PE/EtOAc= 3: 1) to give the title product (2.5 g, yield: 90percent) as a colorless oil. 1H NMR (400 MHz, CDC13) δ: 4.72 (s, 1H), 3.74-3.61 (m, 3H), 3.45-3.42 (m, 1 H), 3.34-3.32 (m, 1H), 2.05-1.08 (m, 4H), 1.45-1.40 (m, 11H). ESI-MS (M+H+-56): 224.0.
Reference: [1] Patent: WO2012/58645, 2012, A1, . Location in patent: Page/Page column 210
[2] Patent: US5932606, 1999, A,
  • 8
  • [ 55052-24-9 ]
  • [ 7143-01-3 ]
  • [ 348640-06-2 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With tetramethylammonium bromide In N,N-dimethyl-formamide; acetonitrile at 0 - 20℃;
Stage #2: With sodium hydroxide In water; N,N-dimethyl-formamide; acetonitrile
Preparation of 1-methyl-4-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (Formula 17); A solution of 70percent mCPBA (11.54 g, 66.87 mmole) in ethyl acetate (25 mL) was added by drops to a solution of 7-azaindole (Formula 11, 5 g, 42.3 mmole) in ethyl acetate (40 mL) at 0° C. with a good stirrer. After addition was completed, the mixture was stirred at room temperature for 1 to 2 hours until no starting material left. The mixture was cooled, filtered, and washed with ethyl acetate to give a solid. It was dissolved in 50 mL of water and treated with 30percent K2CO3 solution (16 mL) to pH 9.5-10.5 to give a precipitate. It was stirred at room temperature for 1 hour, cooled, filtered, and washed with a small amount of cold water to give 2.484 g of 1H-pyrrolo[2,3-b]pyridine 7-oxide as a white crystal (Formula 12, 43.8percent yield). MS (m/z): 135.1 (MH+).A solution of methanesulfonic anhydride (6.066 g, 34.82 mmole) and acetonitrile (11.7 mL) was added by drops to a solution of 1H-pyrrolo[2,3-b]pyridine 7-oxide (Formula 12, 2.333 g, 17.41 mmole), tetramethyl ammonium bromide (4.023 g, 26.12 mmole) in DMF (11.7 mL) at 0° C. After stirring at 0° C. for 45 min, additional DMF (11.7 mL) was added in drops to the thick mixture at 0° C., and then stirred at room temperature overnight. To the mixture was added ice water (35 mL), followed by 10 N NaOH (4.66 mL) to pH 7. After stirring at the room temperature, a precipitate formed. It was filtered and washed with water to give 1.891 g of 4-bromo-1H-pyrrolo[2,3-b]pyridine as a pale peach solid (Formula 13, 55percent yield). MS (m/z): 197 (MH+). NMR (DMSO-d6) showed 69percent impurity which is likely to be the 4,6-dibromo compound based on LC/MS analysis.A mixture of 4-bromo-1H-pyrrolo[2,3-b]pyridine (Formula 13, 197 mg, 1 mmole), dimethylamine hydrochloride (88 mg, 1.079 mmole), and paraformaldehyde (33 mg, 1.1 mmole) in n-butanol (2 mL) was heated at 120° C. for 1.25 hours. After removal of the solvent, the residue was treated with ice water and three drops of con. HCl. After washing with ether, the aqueous layer was basified with sat. K2CO3 solution and extracted with methylene chloride. The organic layer was dried over sodium sulfate, filtered, and the solvent dried to give 106 mg of 1-(4-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-N,N-dimethylmethanamine as a light pink solid (Formula 14, 42percent). MS (m/z): 254.2 (MH+).A solution of 1-(4-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-N,N-dimethylmethanamine (Formula 14, 341 mg, 1.34 mmole) and hexamethylenetetramine (190 mg, 1.34 mmole) in 66percent propionic acid was added by drops to a refluxing solution of hexamethylenetetramine (190 mg, 1.34 mmole) in 66percent propionic acid (0.8 mL) at 120° C. The reaction mixture was heated for 2-4 hours, and monitored by MS. It was cooled, treated with water (4 mL), and filtered to give 238 mg of 4-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde as a beige solid (Formula 15, 79percent). MS (m/z): 225.0 (MH+).Sodium hydride (60percent, 27.4 mg, 0.686 mmole) was added in portions to a suspension of 4-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (Formula 15, 128.6 mg, 0.572 mmole) in 5 mL of DMF and 1 mL of THF at 0° C. After stirring at 0° C. for 20 min, methyl iodide (39.2 μL, 0.6292 mmole) was added by drops into the mixture and warmed up to room temperature for 2.5 hours. The solvents were evaporated and the residue was treated with methylene chloride, filtered, and dried. This was further treated with hexane. The mixture was filtered again and washed with hexane to give a beige solid, which was recrystallized from chloroform and hexane to yield 102 mg of 4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde as crystals (Formula 16, 74percent). MS (ESI): m/z 239 (M+H).A mixture of 4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (Formula 16, 38 mg, 0.159 mmole), phenyl boronic acid (38.8 mg, 0.318 mmole), and tetrakis(triphenylphosphine)palladium (0) (27.6 mg, 0.0238 mmole) in saturated sodium carbonate (0.37 mL) and 1,2-dimethoxylethane (1.4 mL) was heated at 120° C. in microwave for 20 min. It was filtered through a pad of silica gel and washed with 5percent MeOH in ethyl acetate. After the solvent was evaporated, acetonitrile was added to the residue, and filtered to remove a bright yellow solid. The filtrate was concentrated to yield 51.4 mg of 1-methyl-4-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde as white crystals (Formula 17, Ar=phenyl, 76percent). MS (ESI): m/z 237(M+H).
47% With tetrabutylammomium bromide In N,N-dimethyl-formamide at 0 - 20℃; for 4.5 h; 1H- Pyrrolo[2,3-b]pyridine oxide (50 g, 373 mmol) and tetramethylammonium bromide (86 g, 559 mmol) were stirred into DMF (500 ml_) at room temperature and then cooled to 0 0C. Methanesulphonic anhydride was then run into the stirred mixture over about half an hour. Stirring was continued for a further 4 h during which time the reaction warmed to rt. This mixture was then poured onto water (1 L) with stirring and carefully neutralised (pH = 7) by the addition of sodium hydroxide solution. A further amount of water was added (1.5 L) followed by ice so that the temperature of the stirred suspension was reduced to about 10 0C. The solid was then removed by filtration and washed with ice/water. The solid was dried in the air and then stirred in cold DCM (80 mL) for half an hour before being collected by filtration, washed with a further small amount of DCM and then dried. This gave the product, 4-bromo-7f/-pyrrolo[2,3-b]pyridine as a tan solid (34.55 g, 175.3 mmol, 47percent), mp 173-176 0C, RF 0.45 (EtOAc). HPLC indicated 94-95percent purity.
Reference: [1] Patent: US2009/298820, 2009, A1, . Location in patent: Page/Page column 36-37
[2] Patent: WO2007/76320, 2007, A2, . Location in patent: Page/Page column 37
  • 9
  • [ 7143-01-3 ]
  • [ 218780-53-1 ]
Reference: [1] Patent: WO2006/26760, 2006, A2, . Location in patent: Page/Page column 141
  • 10
  • [ 1083057-13-9 ]
  • [ 141-43-5 ]
  • [ 7143-01-3 ]
  • [ 1083057-14-0 ]
YieldReaction ConditionsOperation in experiment
53% With pyridine In N2; water; acetonitrile tert-Butyl-3-(6-amino-3-methylpyridin-2-yl)benzoate
A solution of 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (1 eq) and pyridine (4 eq) in acetonitrile (8 vol) was heated to 70° C. A solution of methanesulfonic anhydride (1.5 eq) in MeCN (2 vol) was added over 50 min via addition funnel while maintaining the temperature at less than 75° C.
The mixture was stirred for an additional 0.5 hours after complete addition.
The mixture was then allowed to cool to ambient.
Ethanolamine (10 eq) was added via addition funnel.
After stirring for 2 hours, water (6 vol) was added and the mixture was cooled to 10° C.
After stirring for 3 hours, the solid was collected by filtration and washed with water (3 vol), 2:1 acetonitrile/water (3 vol), and acetonitrile (2*1.5 vol).
The solid was dried to constant weight (<1percent difference) in a vacuum oven at 50° C. with a slight N2 bleed to afford tert-butyl-3-(6-amino-3-methylpyridin-2-yl)benzoate as a red-yellow solid (53percent yield).
53% With pyridine In water; acetonitrile Preparation of tert-butyl-3-(6-amino-3-methylpyridin-2-yl)benzoate
A solution of 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (1 eq) and pyridine (4 eq) in acetonitrile (8 vol) was heated to 70° C. A solution of methanesulfonic anhydride (1.5 eq) in MeCN (2 vol) was added over 50 min via addition funnel while maintaining the temperature at less than 75° C.
The mixture was stirred for an additional 0.5 hours after complete addition.
The mixture was then allowed to cool to ambient.
Ethanolamine (10 eq) was added via addition funnel.
After stirring for 2 hours, water (6 vol) was added and the mixture was cooled to 10° C.
After stirring for 3 hours, the solid was collected by filtration and washed with water (3 vol), 2:1 acetonitrile/water (3 vol), and acetonitrile (2*1.5 vol).
The solid was dried to constant weight (<1percent difference) in a vacuum oven at 50° C. with a slight N2 bleed to afford tert-butyl-3-(6-amino-3-methylpyridin-2-yl)benzoate as a red-yellow solid (53percent yield).
Reference: [1] Patent: US2011/98311, 2011, A1,
[2] Patent: US9241934, 2016, B2,
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