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[ CAS No. 59937-01-8 ] {[proInfo.proName]}

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Chemical Structure| 59937-01-8
Chemical Structure| 59937-01-8
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Product Details of [ 59937-01-8 ]

CAS No. :59937-01-8 MDL No. :MFCD06205115
Formula : C12H11NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :UKKGDCGESAFSJY-UHFFFAOYSA-N
M.W : 233.29 Pubchem ID :10036966
Synonyms :

Calculated chemistry of [ 59937-01-8 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.17
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 63.64
TPSA : 67.43 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.88
Log Po/w (XLOGP3) : 3.17
Log Po/w (WLOGP) : 2.99
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 3.86
Consensus Log Po/w : 2.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.53
Solubility : 0.0691 mg/ml ; 0.000296 mol/l
Class : Soluble
Log S (Ali) : -4.26
Solubility : 0.0129 mg/ml ; 0.0000554 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.3
Solubility : 0.0117 mg/ml ; 0.0000501 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.82

Safety of [ 59937-01-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 59937-01-8 ]

* 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 [ 59937-01-8 ]
  • Downstream synthetic route of [ 59937-01-8 ]

[ 59937-01-8 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 70454-09-0 ]
  • [ 59937-01-8 ]
YieldReaction ConditionsOperation in experiment
92% With oxygen; copper diacetate In N,N-dimethyl-formamide at 120℃; for 12 h; Molecular sieve General procedure: To a solution of 4-carboxythiazoline or 4-carboxyoxazoline (0.5 mmol) in anhydrous DMF (1 mL) were added molecular sieves (4 Å, 100percent wt) and Cu(OAc)2 (9.1 mg, 0.05 mmol). The reaction mixture was stirred with an O2 balloon at 120 °C for 10-24 h. The resulting mixture was diluted with ethyl acetate and the solution was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to afford 4-carboxythiazole or 4-carboxyoxazole.
Reference: [1] Tetrahedron, 2011, vol. 67, # 38, p. 7406 - 7411
  • 2
  • [ 70-23-5 ]
  • [ 2227-79-4 ]
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YieldReaction ConditionsOperation in experiment
94% at 20℃; for 2 h; Reflux A solution of benzothioamide (3.00 g, 21.87 mmol) in EtOH (70 mL) was treated dropwise with ethyl bromopyruvate (5.10 g, 26.2 mmol) and stirred at room temperature for 30 min before being heated at reflux for 1.5 h. The cooled mixture was diluted with ethyl acetate (200 mL), washed (aqueous NaHC03, brine), dried over anhydrous MgSO4 and evaporated. The residue was purified on the ISCO using a REDISEP® 80 g column (10 to 20percent EtOAc-hexane) to give the title compound (4.82 g, 94percent) as a yellow oil. LCMS (APCI): calcd for C12H12NO2S [M+H]+ m/z 234.05, found 234.1. 1H NMR (CDCl3, 400 MHz) δ ppm: 8.14 - 8.19 (m, 1H), 7.98 - 8.07 (m, 2H), 7.41 - 7.51 (m, 3H), 4.46 (q, J= 7.2 Hz, 2H), 1.44 (t, J= 7.2 Hz, 3H)
85% With sodium carbonate In neat (no solvent)Milling General procedure: General procedure for the preparation of ethyl 2-methylthiazole-4-carboxylate (12a)
An oily mixture of ethyl α-bromopyruvate (9, 2.14 g, 11 mmol) and thioacetamide (10a, 0.75 g, 10 mmol) was ground in presence of Na2CO3 (0.50 g) for 5-6 min.
When it becomes solid, the progress of reaction was monitored with TLC.
On completion of the reaction, water (20 ml) was added to the reaction followed by extraction with chloroform (20 ml).
The organic layer thus separated was dried over anhy. Na2SO4.
Excess of solvent was removed by distillation.
Filtered the crude product and crystallized from aqueous ethanol (83percent) to give pure solid 12a.
Similarly, 12b-12g and 13a-13g were prepared following the above procedure and their formation was confirmed by comparing their melting points with literature values.
76% for 4 h; Reflux A solution of ethyl bromopyruvate (0.68g, 3.5 mmol) and thiobenzamide(0.40 g, 2.9 mmol) in ethanol (25 mL) was heated to reflux for 4 h. The solvent was removed under reduced pressure, and the residue was washed with water (30ml) and extracted with ethyl acetate (3 × 20 mL). The organic layer was driedover anhydrous Na2SO4 and concentrated. The residue waspurified by silica gel column chromatography using a mixture of petroleum ether/ethyl acetate (20:1, v/v) as eluent to afford the desired product (0.52g, 76percent) as a white solid.1H NMR (300 MHz, DMSO-d6) δ:8.96 (s, 1H, ArH), 7.89 (d, J=8.01Hz, 2H, ArH), 7.31 (m, 3H, ArH), 4.39 (q, J=7.12 Hz, 2H, -OCH2), 1.34 (t, J=7.12 Hz, 3H,-CH3).
70% for 2 h; Reflux General procedure: A solution of 2-hydroxy-thiobenzamide 4 (300 mg, 1.96 mmol) and ethyl 3-bromopyruvate (458 mg, 2.35 mmol) in ethanol (15 mL) was heated under reflux for 2h. The reaction progress was monitored by TLC analysis. The solvent was removed in vacuo, and the residue was washed with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography (EtOAc:hexane=1:4) to give compound 1 as a colorless needle shaped solid (350 mg, 1.40 mmol) in 71percent yield. Mp 109–111°C (CH2Cl2–hexane); IR (KBr, cm−1) 3140, 2978, 1720, 1474, 1211; 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 7.60 (dd, J=7.8, 8.8Hz, 1H), 7.35 (m, 1H), 7.08 (dd, J=8.4, 8.4Hz, 1H), 6.92 (m, 1H), 4.42 (q, J=7.1 Hz, 2H), 1.41 (t, J=7.4 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 169.8, 160.9, 157.4, 146.5, 132.9, 127.7, 125.4, 119.9, 118.5, 116.7, 62.0, 14.7; Anal. Calcd for C12H11NO3S: C, 57.82; H, 4.45; N, 5.62; S, 12.86, found: C, 57.78; H, 4.36; N, 5.66; S, 13.12. HR-mass Calcd for: C12H11NO3S [M+H]+: 249.0460; found: m/z 249.0457.
69% at 78℃; for 5 h; At room temperature,4.1 g (30 mmol) of Intermediate C1 was added to the reaction flask, 40 mL of ethanol was added, stirred to dissolve, 6.44 g (33 mmol) of ethyl bromopyruvate was added slowly, and the temperature was raised to 78 ° C for 5 h. Reaction completed, vacuum distillation solvent, Then, 50 mL of water was added, extracted with dichloromethane (3 x 40 mL), and the combined organic layers were washed successively with saturated sodium bicarbonate (3 x 30 mL), washed with saturated brine (2 x 30 mL), dried over anhydrous sodium sulfate, filtered and evaporated to dryness to give 4.8 g of a yellow oil, yield69.0percent.

Reference: [1] Patent: WO2013/163279, 2013, A1, . Location in patent: Paragraph 00226
[2] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 718 - 726
[3] European Journal of Medicinal Chemistry, 2016, vol. 113, p. 246 - 257
[4] Medicinal Chemistry Research, 2013, vol. 22, # 8, p. 3802 - 3811
[5] Tetrahedron, 2013, vol. 69, # 30, p. 6095 - 6099
[6] Patent: CN107033095, 2017, A, . Location in patent: Paragraph 0133; 0134
[7] Journal of Medicinal Chemistry, 1983, vol. 26, # 6, p. 884 - 891
[8] Helvetica Chimica Acta, 1944, vol. 27, p. 1432,1433
[9] Journal of the Chemical Society. Perkin transactions 1, 1966, vol. 16, p. 1357 - 1360
[10] Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 4, p. 437 - 440
[11] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1545 - 1555
[12] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 96 - 107
[13] Medicinal Chemistry Research, 2017, vol. 26, # 10, p. 2557 - 2567
[14] Research on Chemical Intermediates, 2018, vol. 44, # 2, p. 1247 - 1260
  • 3
  • [ 868-59-7 ]
  • [ 100-52-7 ]
  • [ 59937-01-8 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: With sodium hydrogencarbonate In ethanol; water at 60℃; for 8 h;
Stage #2: With [bis(acetoxy)iodo]benzene In dichloromethane at 40℃; for 4 h;
General procedure: Sodium bicarbonate (0.68 g, 8.1 mmol) was added to L-cysteine ethyl ester hydrochloride (1 g, 5.4 mmol) in water (25 mL). A solution of pyruvaldehyde (0.43 g, 5.9 mmol) in ethanol (25 mL) was added to the reaction mixture. The reaction mixture was stirred at 60 oC for 8 h and concentrated to evaporate the solvent under vacuum after the consumption of starting materials (checked by TLC). The reaction mixture was extracted with dichloromethane (2 × 30 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to reduce the solvent to half (30 mL). Iodobenzene diacetate (3.65 g, 11.3 mmol) was added and stirred the reaction mixture at 40 0C for 4 h. After completion of the reaction (monitored by TLC) the solvent was evaporated. The product was purified by column chromatography (5percent Ethyl acetate/hexane).
Reference: [1] Arkivoc, 2018, vol. 2018, # 3, p. 354 - 361
  • 4
  • [ 425392-44-5 ]
  • [ 98-80-6 ]
  • [ 59937-01-8 ]
  • [ 425392-45-6 ]
  • [ 425392-46-7 ]
Reference: [1] Organic Letters, 2002, vol. 4, # 8, p. 1363 - 1365
  • 5
  • [ 2227-79-4 ]
  • [ 59937-01-8 ]
YieldReaction ConditionsOperation in experiment
76% for 4 h; Reflux A solution of ethyl bromopyruvate (0.68g, 3.5mmol) and thiobenzamide (0.40g, 2.9mmol) in ethanol (20mL) was heated at reflux for 4h. The solvent was removed, and the residue was added water (15mL) and extracted with ethyl acetate (3×15mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 20:1, v/v) to afford the title compound (0.52g, 76percent) as a white solid. 1H NMR (300MHz, DMSO‑d6) δ: 8.96 (s, 1H), 7.89 (d, J=8.0Hz, 2H), 7.31 (m, 3H), 4.39 (q, J=7.1Hz, 2H), 1.34 (t, J=7.1Hz, 3H). ESI-MS m/z: 234.1 [M+H]+.
Reference: [1] European Journal of Medicinal Chemistry, 2019, p. 352 - 365
  • 6
  • [ 37128-20-4 ]
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Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 13, p. 1751 - 1753
  • 7
  • [ 89530-19-8 ]
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Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 13, p. 1751 - 1753
  • 8
  • [ 80548-05-6 ]
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Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 16, p. 2671 - 2674
  • 9
  • [ 189228-43-1 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 6, p. 1844 - 1847
  • 10
  • [ 70-23-5 ]
  • [ 2227-79-4 ]
  • [ 59937-01-8 ]
  • [ 31877-30-2 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 4, p. 1137 - 1146
  • 11
  • [ 2227-79-4 ]
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Reference: [1] Patent: US5811429, 1998, A,
  • 12
  • [ 14214-10-9 ]
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Reference: [1] Journal of Heterocyclic Chemistry, 1995, vol. 32, # 3, p. 937 - 940
  • 13
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Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 13, p. 1751 - 1753
  • 14
  • [ 3411-58-3 ]
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Reference: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 6, p. 1844 - 1847
  • 15
  • [ 55-21-0 ]
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Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 113, p. 246 - 257
[2] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 96 - 107
  • 16
  • [ 673476-96-5 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3491 - 3495
  • 17
  • [ 1499-53-2 ]
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Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 16, p. 2671 - 2674
  • 18
  • [ 617-35-6 ]
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Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 123, p. 718 - 726
  • 19
  • [ 100-47-0 ]
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Reference: [1] Patent: CN107033095, 2017, A,
  • 20
  • [ 28170-13-0 ]
  • [ 70-23-5 ]
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Reference: [1] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 5, p. 1449 - 1456
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