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[ CAS No. 60434-13-1 ] {[proInfo.proName]}

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Chemical Structure| 60434-13-1
Chemical Structure| 60434-13-1
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Product Details of [ 60434-13-1 ]

CAS No. :60434-13-1 MDL No. :MFCD02956479
Formula : C9H6ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :NJOPQQPDPYWFFA-UHFFFAOYSA-N
M.W : 195.60 Pubchem ID :108941
Synonyms :

Calculated chemistry of [ 60434-13-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.07
TPSA : 37.38 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) : -6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.5
Log Po/w (XLOGP3) : 1.21
Log Po/w (WLOGP) : 1.12
Log Po/w (MLOGP) : 1.06
Log Po/w (SILICOS-IT) : 2.02
Consensus Log Po/w : 1.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.16
Solubility : 1.36 mg/ml ; 0.00697 mol/l
Class : Soluble
Log S (Ali) : -1.59
Solubility : 5.01 mg/ml ; 0.0256 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.07
Solubility : 0.167 mg/ml ; 0.000853 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.59

Safety of [ 60434-13-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 60434-13-1 ]

* 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 [ 60434-13-1 ]
  • Downstream synthetic route of [ 60434-13-1 ]

[ 60434-13-1 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 872305-97-0 ]
  • [ 60434-13-1 ]
YieldReaction ConditionsOperation in experiment
77% With iron(III) chloride In dimethyl sulfoxide at 100℃; for 1.5 h; General procedure: A mixture of N-methyl-2-oxo-N-phenylacetamide 1a (0.4 mmol) and FeCl3 (10 mol percent) were added in 2 mL DMSO and then stirred under air at 100°C for 1.5 h. After the completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and the solvent was evaporated to dryness. The crude residue was purified by flash chromatography on silica (PE/EA=10/1) to afford pure 1-methylindoline-2,3-dione 2a as a red solid (60 mg, 93percent yield).
70% With pyridinium chlorochromate In dimethyl sulfoxide at 100℃; for 3 h; General procedure: A mixture of N-methyl-2-oxo-N-phenylacetamide (1a, 0.5 mmol) and PCC (0.5 mmol) were added in DMSO (2 mL) with a condenser and then heating for 3 h under air at 100 °C. After the completion of the reaction (monitored by TLC), the reaction mixture was cooled to r.t., diluted with H2O and extracted with EtOAc. The organic layer was washed with sat. brine, dried over anhydrous Na2SO4 and the solvent was evaporated to dryness. The crude residue was purified by flash chromatography on silica (PE–EtOAc, 10:1) to afford pure 1-methylindoline-2,3-dione (2a) as a red solid (66 mg, 82percent yield). 1-Methylindoline-2,3-dione (2a) Yield 82percent; red solid; mp 130–133 °C. 1H NMR (400 MHz, CDCl3): δ = 7.64–7.58 (m, 2 H), 7.14 (t, J = 7.6 Hz, 1 H), 6.92 (d, J = 8.0 Hz,1 H), 3.26 (s, 3 H). 13C NMR (150 MHz, CDCl3): δ = 183.3, 158.1, 151.4, 138.4, 125.1, 123.8, 117.3, 109.9, 26.2. ESI-HRMS: m/z [M + Na+] calcd for C9H7NO2 + Na+: 184.0369; found: 184.0370.
Reference: [1] RSC Advances, 2015, vol. 5, # 125, p. 103280 - 103283
[2] Tetrahedron Letters, 2016, vol. 57, # 1, p. 39 - 42
[3] Synlett, 2016, vol. 27, # 8, p. 1292 - 1296
[4] Journal of the American Chemical Society, 2010, vol. 132, # 26, p. 8900 - 8902
[5] Chemistry - A European Journal, 2007, vol. 13, # 4, p. 1032 - 1046
  • 2
  • [ 17630-76-1 ]
  • [ 74-88-4 ]
  • [ 60434-13-1 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; paraffin oil at 0℃; for 1 h; Inert atmosphere
Stage #2: for 1 h; Inert atmosphere
General procedure: To a stirring solution of indolin-2,3-dione (2.0g, 13.6 mmol, 1.0 equiv.) in anhydrous DMF, sodium hydride (60percent suspension inparaffin oil, 0.65 g, 16.32 mmol, 1.2 equiv.) was slowly added at 0 oCunder inert atmosphere. After 1 h, benzyl bromide (1.78 mL, 14.96 mmol,1.1 equiv.) or prenyl bromide (1.73 mL, 14.96 mmol,1.1 equiv.) or methyl iodide ( 0.93 g, 14.96, 1.1equiv.) was added dropwise. Reaction mixture was stirred for another hour.Completion of the reaction was monitored by TLC. The reaction mixture was thenquenched with aq. NH4Cl, washed with water, extracted into ethylacetate. The ethyl acetate fraction was dried over anhydrous sodiumsulfate. It was evaporated under vacuumto give a solid compound which was purified by column chromatography on silicagel (60-120 mesh) using ethyl acetate-hexane (3:97) mixture as eluent.
Reference: [1] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 4, p. 969 - 973
[2] Organic Letters, 2017, vol. 19, # 12, p. 3119 - 3122
[3] Medicinal Chemistry Research, 2007, vol. 15, # 9, p. 492 - 510
[4] Journal of Organic Chemistry, 2017, vol. 82, # 16, p. 8548 - 8567
[5] Tetrahedron Letters, 2015, vol. 56, # 51, p. 7074 - 7081
[6] Angewandte Chemie - International Edition, 2006, vol. 45, # 20, p. 3353 - 3356
[7] Chemical Communications, 2017, vol. 53, # 10, p. 1684 - 1687
[8] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 17, p. 2427 - 2430
[9] European Journal of Medicinal Chemistry, 2010, vol. 45, # 3, p. 1068 - 1077
[10] Journal of the American Chemical Society, 2010, vol. 132, # 43, p. 15328 - 15333
[11] Green Chemistry, 2011, vol. 13, # 9, p. 2553 - 2560
[12] Synlett, 2011, # 15, p. 2256 - 2258
[13] European Journal of Organic Chemistry, 2012, # 12, p. 2359 - 2366
[14] Chemistry - A European Journal, 2012, vol. 18, # 31, p. 9645 - 9650
[15] Synlett, 2012, vol. 23, # 15, p. 2274 - 2278
[16] Chemistry - An Asian Journal, 2012, vol. 7, # 10, p. 2446 - 2449,4
[17] Chemistry - An Asian Journal, 2012, vol. 7, # 10, p. 2446 - 2449
[18] Angewandte Chemie - International Edition, 2013, vol. 52, # 41, p. 10780 - 10783[19] Angew. Chem., 2013, vol. 125, # 41, p. 10980 - 10983
[20] Chemistry - A European Journal, 2014, vol. 20, # 20, p. 5905 - 5909
[21] Chemistry - A European Journal, 2016, vol. 22, # 8, p. 2595 - 2598
[22] Organic Letters, 2014, vol. 16, # 12, p. 3192 - 3195
[23] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 4, p. 457 - 468
[24] Journal of Organic Chemistry, 2014, vol. 79, # 22, p. 11161 - 11169
[25] European Journal of Medicinal Chemistry, 2015, vol. 102, p. 413 - 424
[26] Organic Letters, 2016, vol. 18, # 20, p. 5232 - 5235
[27] Journal of Organic Chemistry, 2016, vol. 81, # 20, p. 9757 - 9764
[28] Advanced Synthesis and Catalysis, 2017, vol. 359, # 1, p. 49 - 57
[29] Tetrahedron Letters, 2017, vol. 58, # 27, p. 2636 - 2639
[30] Advanced Synthesis and Catalysis, 2017, vol. 359, # 22, p. 3934 - 3939
[31] Journal of Organic Chemistry, 2017, vol. 82, # 19, p. 10121 - 10128
[32] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7622 - 7632
[33] Journal of Fluorine Chemistry, 2018, vol. 215, p. 44 - 51
[34] Journal of Organic Chemistry, 2018,
[35] European Journal of Medicinal Chemistry, 2019, p. 147 - 160
  • 3
  • [ 41192-33-0 ]
  • [ 60434-13-1 ]
YieldReaction ConditionsOperation in experiment
81% With tert.-butylnitrite; oxygen In tetrahydrofuran at 50℃; for 24 h; Schlenk technique; Inert atmosphere General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 °C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.
80% With tert.-butylhydroperoxide In 1,2-dichloro-ethane at 85℃; for 24 h; Schlenk technique General procedure: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time until complete consumption of starting material monitored by TLC analysis. After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).
Reference: [1] Synlett, 2017, vol. 28, # 17, p. 2307 - 2310
[2] Synlett, 2018, vol. 29, # 2, p. 215 - 218
  • 4
  • [ 33280-23-8 ]
  • [ 60434-13-1 ]
YieldReaction ConditionsOperation in experiment
98.9% With copper acetylacetonate; diethylmethylsilane; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide In toluene at 80℃; for 7 h; In an open environment, lmmo 1 of compound of formula (I) and 6 ml of solvent toluene are added to the kettle at room temperature and then0.07 mmol of Cu (acac) 2 catalyst and 80 mg of a mixture of HSiEt2Me and 1-butyl-3-methylimidazolium trifluoromethanesulfonimide salt in a mass ratio of 1: 4 were added and the temperature was gradually increased to 80 ° with stirring C reaction 7h, after the reaction was cooled to room temperature, the mixture was added 9 times the solvent amount of a mixture of ether and water, wherein the mass ratio of ether and water 1: 1, the aqueous phase was extracted with ether, the organic layer was combined The mixture was dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was purified by column chromatography on silica gel to give the compound of formula (II). The yield was 98.9percent and the purity was 98.8percent (HPLC).
Reference: [1] Patent: CN104059012, 2016, B, . Location in patent: Paragraph 0033 - 0035; 0048; 0054; 0059; 0063
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 21, p. 3349 - 3353
  • 5
  • [ 112398-75-1 ]
  • [ 60434-13-1 ]
YieldReaction ConditionsOperation in experiment
73% With C7H4IO7S(1-)*K(1+); sodium iodide In water; dimethyl sulfoxide at 60℃; for 16 h; General procedure: In a 4 mL vial, the starting indole 5 (0.27 mmol) was dissolved in a 2:1 mixture of DMSO and H2O (2.7 mL, 0.1 M). IBX-SO3K (2; 322 mg, 0.81 mmol, 3 equiv) followed by NaI (48 mg, 0.32 mmol, 1.2 equiv) were added to the reaction mixture at r.t. The mixture was then stirred for 16 h at 60 °C. Upon full conversion (as indicated by TLC, eluent: pentanes–EtOAc, 60:40), the mixture was added to H2O (30 mL) and extracted with EtOAc (3 × 10 mL). The combined organic layers were washed with brine (15 mL) and dried (Na2SO4). The solvent was re-moved under reduced pressure and the isatin product 6 was purified by column chromatography over silica gel (Table 1).
72% With tert.-butylhydroperoxide; copper diacetate In water; acetonitrile at 50℃; for 12 h; General procedure: Cu(OAc)2 (0.025 mmol), indoles (0.5 mmol), TBHP (1 mL, 70 percent solution in water) and CH3CN (3.0 mL) were added to glass tube via syringe. The reaction mixture was stirred at 50°C for 12 h. It was then quenched (consumption of residual TBHP) with saturated Na2SO3 solution and extracted with EtOAc. The organic layer was combined and dried with Na2SO4. Removal of solvent followed by flash column chromatographic purification (Ethyl acetate/Petroleum ether=5/1) afforded products.
63% With tert.-butylhydroperoxide; palladium diacetate In water; acetonitrile at 80℃; for 1 h; General procedure: Pd(OAc)2 (0.05 mmol), indole derivative 1 (0.5 mmol), TBHP (1 mL, 70 percent solutionin water) and CH3CN (3.0 mL) were added to a vial. The reaction mixture was stirredunder 80 °C for 1 h. After that time, the reaction mixture was quenched with saturatedNa2SO3 solution (consumption of residual TBHP) and extracted with EtOAc. Theorganic layer was separated and dried with Na2SO4. Removal of solvent followed byflash column chromatographic purification (Ethyl acetate/Petroleum ether = 5/1)afforded products.
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 22, p. 2762 - 2767
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 12, p. 2105 - 2109
[3] Synthesis (Germany), 2015, vol. 47, # 13, p. 1937 - 1943
[4] Tetrahedron Letters, 2017, vol. 58, # 49, p. 4591 - 4594
[5] ACS Catalysis, 2016, vol. 6, # 10, p. 6853 - 6860
[6] Synlett, 2018, vol. 29, # 7, p. 969 - 973
  • 6
  • [ 74-83-9 ]
  • [ 17630-76-1 ]
  • [ 60434-13-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 521 - 530
[2] European Journal of Medicinal Chemistry, 2017, vol. 139, p. 250 - 262
[3] Bioorganic Chemistry, 2018, vol. 81, p. 425 - 432
[4] Monatshefte fur Chemie, 2017, vol. 148, # 4, p. 757 - 764
[5] Journal of Enzyme Inhibition and Medicinal Chemistry, 2018, vol. 33, # 1, p. 686 - 700
[6] European Journal of Medicinal Chemistry, 2018, vol. 160, p. 49 - 60
  • 7
  • [ 62903-71-3 ]
  • [ 60434-13-1 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 14, p. 2878 - 2882
[2] Journal of Organic Chemistry, 2014, vol. 79, # 11, p. 4984 - 4991
[3] Organic Letters, 2013, vol. 15, # 22, p. 5726 - 5729
  • 8
  • [ 847550-39-4 ]
  • [ 60434-13-1 ]
Reference: [1] Chemistry - A European Journal, 2007, vol. 13, # 4, p. 1032 - 1046
  • 9
  • [ 41192-33-0 ]
  • [ 60434-13-1 ]
Reference: [1] Chemical Communications, 2018, vol. 54, # 59, p. 8265 - 8268
  • 10
  • [ 131543-46-9 ]
  • [ 932-96-7 ]
  • [ 60434-13-1 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 20, p. 3484 - 3489
  • 11
  • [ 106-47-8 ]
  • [ 60434-13-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 17, p. 2427 - 2430
[2] Green Chemistry, 2011, vol. 13, # 9, p. 2553 - 2560
[3] European Journal of Medicinal Chemistry, 2015, vol. 102, p. 413 - 424
[4] Tetrahedron Letters, 2015, vol. 56, # 51, p. 7074 - 7081
[5] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7622 - 7632
  • 12
  • [ 2058-74-4 ]
  • [ 60434-13-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 42, p. 7372 - 7386
[2] Journal of the Brazilian Chemical Society, 2011, vol. 22, # 2, p. 257 - 263
  • 13
  • [ 79-37-8 ]
  • [ 698-69-1 ]
  • [ 60434-13-1 ]
Reference: [1] Synthesis, 2001, # 6, p. 904 - 908
  • 14
  • [ 17630-76-1 ]
  • [ 77-78-1 ]
  • [ 60434-13-1 ]
Reference: [1] Gazzetta Chimica Italiana, 1955, vol. 85, p. 840,841
[2] Chemische Berichte, 1926, vol. 59, p. 708
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982, vol. 21, # 1, p. 72 - 74
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 280 - 285
  • 15
  • [ 698-69-1 ]
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Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 18, p. 3475 - 3478
  • 16
  • [ 65798-06-3 ]
  • [ 60434-13-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 17, p. 2427 - 2430
[2] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7622 - 7632
  • 17
  • [ 872492-58-5 ]
  • [ 60434-13-1 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 14, p. 2878 - 2882
  • 18
  • [ 26772-93-0 ]
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 10, p. 1619 - 1625
  • 19
  • [ 17630-76-1 ]
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Reference: [1] Synthetic Communications, 2012, vol. 42, # 18, p. 2715 - 2727
  • 20
  • [ 77-78-1 ]
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Reference: [1] Journal of the Indian Chemical Society, 1982, vol. 59, # 10, p. 1174 - 1176
  • 21
  • [ 91-56-5 ]
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Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 42, p. 7372 - 7386
  • 22
  • [ 208177-08-6 ]
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 10, p. 1619 - 1625
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