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[ CAS No. 348-40-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 348-40-3
Chemical Structure| 348-40-3
Chemical Structure| 348-40-3
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Product Details of [ 348-40-3 ]

CAS No. :348-40-3 MDL No. :MFCD00013336
Formula : C7H5FN2S Boiling Point : -
Linear Structure Formula :- InChI Key :CJLUXPZQUXVJNF-UHFFFAOYSA-N
M.W :168.19 Pubchem ID :319954
Synonyms :

Calculated chemistry of [ 348-40-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.98
TPSA : 67.15 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) : -5.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 2.06
Log Po/w (WLOGP) : 2.45
Log Po/w (MLOGP) : 1.69
Log Po/w (SILICOS-IT) : 2.85
Consensus Log Po/w : 2.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.79
Solubility : 0.275 mg/ml ; 0.00164 mol/l
Class : Soluble
Log S (Ali) : -3.1
Solubility : 0.134 mg/ml ; 0.000796 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.88
Solubility : 0.22 mg/ml ; 0.00131 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.15

Safety of [ 348-40-3 ]

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 [ 348-40-3 ]

* 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 [ 348-40-3 ]
  • Downstream synthetic route of [ 348-40-3 ]

[ 348-40-3 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 348-40-3 ]
  • [ 399-74-6 ]
YieldReaction ConditionsOperation in experiment
83% With tert.-butylnitrite; copper dichloride In acetonitrile at 65℃; for 2 h; To a round bottomed flask was added 2-amino-6-fluorobenzothiazole (1.0017 g, 5.96 mmol, Sigma-Aldrich Chemical Company, Inc.), copper (II) chloride (1.201 g, 8.93 mmol, Sigma-Aldrich Chemical Company, Inc.), and tert-butyl nitrite (1.063 ml, 8.93 mmol, Acros Organics) in ACN and was heated to 65° C. for 2 hours.
The reaction mixture was diluted with 1N HCl and extracted with EtOAc.
The organic extract was washed with water, satd NaCl, dried over MgSO4, filtered and concentrated in vacuo to give the title compound (0.9249 g, 4.93 mmol, 83percent yield).
1H NMR (400 MHz, DMSO-d6) δ ppm s 7.45 (td, J=9.10, 2.74 Hz, 1H) 7.97-8.07 (m, 2H)
64% With copper(II) choride dihydrate; isopentyl nitrite In acetonitrile at 65℃; for 3 h; Intermediates 2: a) 2-Chloro-6-fluoro-benzothiazole (2a); 0.5 g (2.97 mmol) of 6-fluoro-benzothiazol-2-ylamine is placed in the presence of isoamyl nitrite (0.52 g, 4.46 mmol) and CuCI2.2H20 (0.61 g, 0.57 mmol) in 10 mL of acetonitrile. The reaction medium is heated to 65°C for 3h and then reduced to dryness; the residue is taken up by water and extracted using ethyl acetate. The organic phases are dried and then evaporated, and the residue obtained is purified by flash chromatography on silica (CH2CI2-AcOEt, gradient 100-0 to 97-3 over 30 min). 0.36 g of solid is obtained (yield 64percent). TLC silica gel 60 F 254 Merck, CH2CI2- MeOH:95-5, Rf=0.84.
64% With copper(II) choride dihydrate; isopentyl nitrite In acetonitrile at 65℃; for 3 h; a)
2-Chloro-6-fluoro-benzothiazole (2a)
0.5 g (2.97 mmol) of 6-fluoro-benzothiazol-2-ylamine is placed in the presence of isoamyl nitrite (0.52 g, 4.46 mmol) and CuCl2.2H2O (0.61 g, 0.57 mmol) in 10 mL of acetonitrile.
The reaction medium is heated to 65° C. for 3 h and then reduced to dryness; the residue is taken up by water and extracted using ethyl acetate.
The organic phases are dried and then evaporated, and the residue obtained is purified by flash chromatography on silica (CH2Cl2-AcOEt, gradient 100-0 to 97-3 over 30 min).
0.36 g of solid is obtained (yield 64percent). TLC silica gel 60 F 254 Merck, CH2Cl2-MeOH:95-5, Rf=0.84.
Reference: [1] Patent: US2013/225552, 2013, A1, . Location in patent: Paragraph 0976
[2] Patent: WO2012/69503, 2012, A1, . Location in patent: Page/Page column 18-19
[3] Patent: US2013/172326, 2013, A1, . Location in patent: Paragraph 0081; 0082
[4] Journal of the Indian Chemical Society, 1933, vol. 10, p. 465,469
[5] Farmaco, Edizione Scientifica, 1977, vol. 32, p. 348 - 354
[6] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 4022 - 4025
[7] Chemistry and Biodiversity, 2011, vol. 8, # 2, p. 253 - 265
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049
[9] Organic Letters, 2017, vol. 19, # 21, p. 5836 - 5839
  • 2
  • [ 333-20-0 ]
  • [ 371-40-4 ]
  • [ 348-40-3 ]
YieldReaction ConditionsOperation in experiment
84% at 5 - 6℃; for 2 h; General procedure: Arylamine (0.1 mol) and potassiumthiocyanate (0.4 mol) were dissolved in glacial aceticacid (40 mL) and cooled. Bromine (0.04 mol) mixed withglacial acetic acid (24 mL) was added from droppingfunnel at such a rate that temperature does not rise beyond5–6°C. After all bromine had been added, the solutionwas stirred with glass rod for an additional 2 h at lowtemperature. The mixture was allowed to stand overnight,during which period orange-yellow precipitates get settledat the bottom. Water was added and slurry formed washeated at 850°C on steam bath for 20 min and fi ltered hot.The fi ltrate was cooled and neutralised with ammoniasolution to pH 6. Yellow precipitates obtained werecollected, washed with water and recrystallized frombenzene to get crystals of 1,3-benzothiazol-2-amine andits derivatives 1-3 [21, 22].
80%
Stage #1: at 20℃; Cooling with ice
Stage #2: With ammonium hydroxide In water
General procedure: A mixture of 0.1 mol of 4-substituted aniline and 0.1 mol of Potassium thiocyanate (KCNS) in 100 ml glacial acetic acid (AcOH) was cooled in an ice bath and stirred for 10-20 min, and then 0.1 mol bromine in glacial acetic acid was added dropwise at such a rate to keep the temperature below 10 °C throughout the addition. The reaction mixture was stirred at room temperature for 2-4 h, the hydrobromide (HBr) salt thus separated out was filtered, washed with acetic acid, dried, dissolved in hot water and basified to pH 11.0 with ammonia solution (NH4OH) and the resulting precipitate was filtered, washed with water and dried to get the desired product 3a-k. The progress of the reaction was monitored by Thin Layer Chromatography using toluene: acetone (8:2) solvent system.
77.3%
Stage #1: at -10 - 20℃; for 12.5 h;
Stage #2: With ammonium hydroxide In waterHeating
General procedure: An appropriately p-substituted aniline (0.1 mol) and potassiumthiocyanate (KCNS, 9.718 g, 0.1 mol) were dissolvedin 100 mL of glacial acetic acid (AcOH), cooled inice–salt mixture and stirred mechanically, while a solutionof bromine (15.980 g, 0.1 mol) in AcOH (20 mL)was slowly added drop by drop (Palkar et al. 2010).External cooling was applied throughout the process to keepthe temperature below 10 °C and the stirring was continuedfor 30 min. After all of the bromine had been added, thesolution was stirred for 2 h below room temperature and atroom temperature for 10 h. It was then allowed to standovernight during which the precipitate of imino-benzo[d]thiazole hydrobromide salt thus separated out was filtered,washed with acetic acid, dried, dissolved in hot water andbasified to pH 11.0 with ammonia solution (NH4OH) andthe resulting precipitate was filtered, washed with water anddried to get the desired products 2-amino-6-substitutedbenzo[d]thiazole (1a–d). The progress of the reaction wasmonitored by TLC using acetone (20percent) in toluene solvent.
Reference: [1] Organic Letters, 2017, vol. 19, # 21, p. 5836 - 5839
[2] Molecular Crystals and Liquid Crystals, 2013, vol. 575, # 1, p. 64 - 76
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8599 - 8607
[4] Russian Journal of Applied Chemistry, 2015, vol. 88, # 12, p. 2065 - 2073[5] Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.),
[6] European Journal of Medicinal Chemistry, 2008, vol. 43, # 5, p. 1114 - 1122
[7] Archiv der Pharmazie, 2015, vol. 348, # 4, p. 254 - 265
[8] European Journal of Medicinal Chemistry, 2012, vol. 53, p. 41 - 51
[9] Medicinal Chemistry Research, 2017, vol. 26, # 9, p. 1969 - 1987
[10] Journal of Organic Chemistry, 2017, vol. 82, # 18, p. 9312 - 9320
[11] Journal of Pharmaceutical Sciences, 1994, vol. 83, # 10, p. 1425 - 1432
[12] Journal of Medicinal Chemistry, 1999, vol. 42, # 15, p. 2828 - 2843
[13] Journal of the Indian Chemical Society, 2008, vol. 85, # 3, p. 333 - 335
[14] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 11, p. 3443 - 3446
[15] Archiv der Pharmazie, 2010, vol. 343, # 6, p. 353 - 359
[16] Patent: WO2011/151361, 2011, A1, . Location in patent: Page/Page column 53-54
[17] Asian Journal of Chemistry, 2011, vol. 23, # 9, p. 3969 - 3974
[18] Asian Journal of Chemistry, 2010, vol. 22, # 7, p. 5487 - 5492
[19] Heteroatom Chemistry, 2012, vol. 23, # 4, p. 399 - 410
[20] Organic Letters, 2012, vol. 14, # 20, p. 5334 - 5337,4
[21] Journal of Enzyme Inhibition and Medicinal Chemistry, 2013, vol. 28, # 1, p. 1 - 10
[22] European Journal of Medicinal Chemistry, 2013, vol. 67, p. 1 - 13
[23] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 24 - 30
[24] Archiv der Pharmazie, 2013, vol. 346, # 11, p. 819 - 831
[25] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 2, p. 459 - 465
[26] Chemical Biology and Drug Design, 2014, vol. 84, # 1, p. 123 - 129
[27] Medicinal Chemistry, 2013, vol. 9, # 4, p. 596 - 607
[28] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 6, p. 1641 - 1658
[29] Research on Chemical Intermediates, 2015, vol. 41, # 8, p. 5599 - 5609
[30] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 23, p. 5561 - 5565
[31] Research on Chemical Intermediates, 2016, vol. 42, # 12, p. 8329 - 8344
[32] Archiv der Pharmazie, 2018, vol. 351, # 12,
  • 3
  • [ 1147550-11-5 ]
  • [ 371-40-4 ]
  • [ 348-40-3 ]
YieldReaction ConditionsOperation in experiment
78% With bromine In dichloromethane at 20℃; for 16 h; General procedure: To a mixture of aniline (1) (2.0 g, 0.021 mol) and ammonium thiocyanate (6.5 g, 0.086 mol), bromine (2.2 mL, 0.043 mol) in dichloromethane (20 mL) and stirred for 16 h at ambient temperature. Later than water was added to the reaction mixture and the product was extracted in dichloromethane (3 × 30 mL). The solvent was evaporated under vacuum to afford the as crude, which was further purified by column chromatography using EtOAc:Hexane (4:6) to give compounds 2a-d.
Reference: [1] Heterocyclic Communications, 2002, vol. 8, # 3, p. 275 - 280
[2] Asian Journal of Chemistry, 2015, vol. 27, # 12, p. 4575 - 4578
[3] European Journal of Organic Chemistry, 2011, # 31, p. 6206 - 6217
[4] Journal of Organic Chemistry, 2018, vol. 83, # 19, p. 12129 - 12142
[5] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 1, p. 131 - 136
[6] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 4022 - 4025
[7] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 4, p. 527 - 534
[8] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049
[9] European Journal of Medicinal Chemistry, 2018, vol. 148, p. 477 - 486
  • 4
  • [ 371-40-4 ]
  • [ 348-40-3 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: at 10℃;
Stage #2: at 10 - 20℃; for 4 h;
General procedure: A mixture of aniline (0.05mol) and NH4SCN (19.03g, 0.25mol) in glacial acetic acid (100mL) was cooled to 10°C in an ice bath and stirred for 10–20min. Then bromine (2.82mL, 0.055mol) in glacial acetic acid was added drop wise at such a rate to keep the temperature below 10°C. The mixture was stirred at room temperature for 4h and then poured into hot water (500mL), and basified to pH 11.0 with ammonia solution (NH4OH). The resulting precipitate was filtered, washed with water and dried to get a light yellow to brown solid. The crude product was purified by chromatography on silica gel using MeOH/CH2Cl2 to afford compounds 2a–2k in good yields.
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1759 - 1775
[2] European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 4293 - 4299
[3] Archiv der Pharmazie, 2010, vol. 343, # 11-12, p. 692 - 699
  • 5
  • [ 371-40-4 ]
  • [ 348-40-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1981, vol. 18, # 4, p. 759 - 761
  • 6
  • [ 459-05-2 ]
  • [ 348-40-3 ]
Reference: [1] Biological and Pharmaceutical Bulletin, 2002, vol. 25, # 3, p. 335 - 341
[2] Journal of the Indian Chemical Society, 1931, vol. 8, p. 147,163
[3] Patent: US2033949, 1933, ,
[4] Journal of the Chemical Society [Section] C: Organic, 1969, p. 268 - 272
[5] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 16, p. 5678 - 5682
[6] Acta Poloniae Pharmaceutica - Drug Research, 2009, vol. 66, # 4, p. 387 - 392
[7] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4211 - 4222
[8] Chemical Biology and Drug Design, 2016, p. 354 - 362
[9] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9814 - 9824
[10] Patent: US2061186, 1933, ,
  • 7
  • [ 371-40-4 ]
  • [ 348-40-3 ]
Reference: [1] Journal of the Indian Chemical Society, 1931, vol. 8, p. 147,163
[2] Journal of the Chemical Society [Section] C: Organic, 1969, p. 268 - 272
[3] Medicinal Chemistry Research, 2013, vol. 22, # 1, p. 195 - 210
[4] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4211 - 4222
[5] Journal of Chemical Research, 2014, vol. 38, # 10, p. 611 - 616
[6] Chemical Biology and Drug Design, 2016, p. 354 - 362
[7] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9814 - 9824
  • 8
  • [ 2146-07-8 ]
  • [ 348-40-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 16, p. 5678 - 5682
[2] Biological and Pharmaceutical Bulletin, 2002, vol. 25, # 3, p. 335 - 341
[3] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4211 - 4222
  • 9
  • [ 540-72-7 ]
  • [ 371-40-4 ]
  • [ 348-40-3 ]
Reference: [1] Die Pharmazie, 1967, vol. 22, # 6, p. 229 - 233
  • 10
  • [ 1544-68-9 ]
  • [ 348-40-3 ]
Reference: [1] Journal of the Indian Chemical Society, 1931, vol. 8, p. 147,163
  • 11
  • [ 1111-67-7 ]
  • [ 371-40-4 ]
  • [ 348-40-3 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 189 - 190
  • 12
  • [ 348-40-3 ]
  • [ 63754-96-1 ]
Reference: [1] Farmaco, Edizione Scientifica, 1977, vol. 32, p. 348 - 354
  • 13
  • [ 348-40-3 ]
  • [ 78364-55-3 ]
YieldReaction ConditionsOperation in experiment
89% With hydrogenchloride; hydrazine hydrate In water at 5℃; for 5 h; Reflux 6-Fluoro-2-hydrazinobenzothiazole (2). Hydrochloric acid (10 mL) was added dropwise to hydrazine hydrate 99percent (10 g, 0.2 mol) at 5-10 °C, followed by addition of a solution of 2-amino-6-fluorobenzothiazole (1) (3.364 g, 0.02 mol) in ethylene glycol (40 mL). The mixture was heated at reflux temperature for 5 h. On cooling, the precipitated solid was collected by filtration, washed with water, dried and crystallized from ethanol. Yield 89percent, m.p. 194-196 °C [1].
Reference: [1] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 2, p. 459 - 465
[2] Chinese Chemical Letters, 2015, vol. 26, # 12, p. 1522 - 1528
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 4022 - 4025
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. <B> 20, # 4, p. 314 - 316
[5] European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 4293 - 4299
[6] Archiv der Pharmazie, 2010, vol. 343, # 11-12, p. 692 - 699
[7] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 4, p. 527 - 534
[8] Journal of the Indian Chemical Society, 2008, vol. 85, # 3, p. 333 - 335
[9] Chemistry and Biodiversity, 2011, vol. 8, # 2, p. 253 - 265
[10] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049
[11] Journal of Medicinal Chemistry, 2013, vol. 56, # 13, p. 5514 - 5540
[12] Chinese Chemical Letters, 2016, vol. 27, # 3, p. 380 - 386
[13] Chemical Biology and Drug Design, 2016, p. 354 - 362
[14] Research on Chemical Intermediates, 2016, vol. 42, # 12, p. 8329 - 8344
  • 14
  • [ 348-40-3 ]
  • [ 152937-04-7 ]
YieldReaction ConditionsOperation in experiment
40% With tert.-butylnitrite; copper(I) bromide In acetonitrile at 60℃; for 1 h; General procedure: To a stirred suspension of CuBr (1.57 g, 10.9 mmol) in MeCN (25 ml) was added tBuONO (1.63 ml, 13.7 mmol) and the mixture was stirred at 60 °C for 10 min. Then 2-amino-6-methylbenzothiazole (14b) (1.50 g, 9.13 mmol) was added to the mixture, and the reaction mixture was stirred at 60 °C for 1 h. After cooled to room temperature, the mixture was poured into 1 N HCl. The resulting precipitate was dissolved into EtOAc, washed with 1 N HCl, brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica gel with n-hexane-EtOAc (7:1, v/v) as eluent to give the title compound (703 mg, 34percent) as a brown oil.
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 3, p. 1201 - 1212
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 18, p. 5919 - 5923
  • 15
  • [ 348-40-3 ]
  • [ 7787-70-4 ]
  • [ 152937-04-7 ]
YieldReaction ConditionsOperation in experiment
40% With tert.-butylnitrite In hexane; ethyl acetate; acetonitrile (Step 1)
Synthesis of 2-bromo-6-fluorobenzothiazole
Copper (I) bromide (619 mg, 4.32 mmol) was suspended in acetonitrile (10 ml).
To the resulting suspension was added tert-butyl nitrite (640 ael, 5.38 mmol), followed by stirring at 60OEC for 5 minutes.
To the reaction mixture was added 2-amino-6-fluorobenzothiazole (605 mg, 3.60 mmol).
The resulting mixture was stirred at 60OEC for 10 minutes.
After cooling to the room temperature, the reaction mixture was diluted with ethyl acetate.
The ethyl acetate solution was washed with 1N HCl, saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent.
The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ ethyl acetate (5:1, v/v) eluate fractions, 2-bromo-6-fluorobenzothiazole (330 mg, 40percent) was obtained as a brown solid.
1H-NMR (CDCl3) δ: 7.19-7.24 (m, 1H), 7.49-7.52 (m, 1H), 7.92-7.96 (m, 1H).
MS (ESI) m/z 273.8 (M++1+MeCN).
Reference: [1] Patent: EP1346982, 2003, A1,
[2] Patent: US5371093, 1994, A,
  • 16
  • [ 75-15-0 ]
  • [ 348-40-3 ]
  • [ 80087-71-4 ]
Reference: [1] Patent: US5451594, 1995, A,
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