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[ CAS No. 96929-05-4 ] {[proInfo.proName]}

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Chemical Structure| 96929-05-4
Chemical Structure| 96929-05-4
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Product Details of [ 96929-05-4 ]

CAS No. :96929-05-4 MDL No. :MFCD09878704
Formula : C12H18N2O4S Boiling Point : -
Linear Structure Formula :- InChI Key :IIBLNWWFRAOZDR-UHFFFAOYSA-N
M.W : 286.35 Pubchem ID :9925901
Synonyms :

Calculated chemistry of [ 96929-05-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.58
Num. rotatable bonds : 8
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 71.72
TPSA : 105.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.33
Log Po/w (XLOGP3) : 2.04
Log Po/w (WLOGP) : 2.19
Log Po/w (MLOGP) : 0.54
Log Po/w (SILICOS-IT) : 2.56
Consensus Log Po/w : 2.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.57
Solubility : 0.776 mg/ml ; 0.00271 mol/l
Class : Soluble
Log S (Ali) : -3.89
Solubility : 0.037 mg/ml ; 0.000129 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.13
Solubility : 0.214 mg/ml ; 0.000746 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.35

Safety of [ 96929-05-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 96929-05-4 ]

* 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 [ 96929-05-4 ]
  • Downstream synthetic route of [ 96929-05-4 ]

[ 96929-05-4 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 70-23-5 ]
  • [ 89226-13-1 ]
  • [ 96929-05-4 ]
YieldReaction ConditionsOperation in experiment
89.6%
Stage #1: at 20 - 25℃; for 5 h;
Stage #2: With sodium hydroxide In water; isopropyl alcohol
Method A:; [00082] At 20-25° C., 24.6 mmol of ethyl bromopyruvate were added to 5.0 g (24.2 mmol) of thioamide in 47 ml of isopropanol, and the mixture was stirred for 5 h. 24.0 mmol of NaOH as a 20percent strength aqueous solution of sodium hydroxide were then added, the product was extracted with methyl tert-butyl ether, the organic phase was washed with water and saturated sodium chloride solution and dried over sodium sulfate and the solvent was completely stripped off. This gave 6.2 g of the ethyl thiazole carboxylate, corresponding to a yield of 89.6percent. [00083] 1H-NMR (DMSO-d6, in ppm): 8.41 (s, 1H, Ar-H), 7.86 (t, broad, NH), 4.41 (d, 2H, CH2), 4.30 (q, 2H, CH2), 1.40 (s, 9H, tert-butyl), 1.30 (t, 3H, CH3).
85% With calcium carbonate In ethanol for 12 h; Compound 24 (10.53g, 55 . 4mmol) dissolved in anhydrous ethanol (100 ml), added calcium carbonate (11.08g, 111mmol), instillment bromo pyruvic acid ethyl ester (10.4 ml, 83mmol), reaction 12h through the diatomite filter, decompression turns on lathe ethanol, the residue is dissolved in ethyl acetate (300 ml) is dissolved, the organic phase is washed with saturated sodium bicarbonate solution, dried anhydrous sodium sulfate, after concentrating the residue by silica gel column chromatography, the obtained crude product with petroleum ether and ethyl acetate is recrystallized to get white solid compound 25 (13.47g, 85percent).
81.7%
Stage #1: With potassium hydrogencarbonate In ethanol at 20 - 25℃;
Stage #2: With sodium hydroxide In ethanol; water
Method B:; [00085] At 20-25° C., 1.07 mol of ethyl bromopyruvate were added to 200 g (1.05 mol) of thioamide in 2.0 l of ethanol and 105 g of KHCO3 powder, and the mixture was stirred overnight. 225 ml of water and 50 g of 20percent strength aqueous sodium hydroxide solution were then added, about 600 ml of ethanol were distilled off, 500 ml of water were added and the mixture was cooled to 0° C. The precipitated solid was filtered off and dried. This gave 246 g of ethyl thiazole carboxylate which, according to NMR, was pure. This corresponds to a yield of 81.7percent.
67%
Stage #1: at 20℃; for 5 h;
Stage #2: for 16 h; Heating / reflux
Stage #3: With di-<i>tert</i>-butyl dicarbonate; triethylamine In ethanol; dichloromethane at 20℃; for 5 h;
To compound 387 (6.00 g, 31.5 mmol) dissolved in CH2CI2 (150 mL) was added ethyl bromopyruvate (6.76 g, 4.4 mL, 34.7 mmol). Stirred at room temperature for 5 h then concentrated. Added 3 A sieves (6 g) and EtOH (150 mL) and refluxed for 16 h. Filtered and concentrated to give a dark foam. Dissolved foam in 1:1 CH2CI2:EtOH (100 mL) and added triethylamine (6.40 g, 8.8 mL, 63.1 mmol) and tBOC anhydride (7.60 g, 34.7 mmol). Stirred at room temperature for 5 h then concentrated. Added 0.25 N NaOH (100 mL), extracted with CH2CI2, dried combined organic extracts (MgS04), filtered, and concentrated. Purified by silica gel chromatography (eluant: 10percent EtOAc- CH2Cl2 to 30percent EtOAc-CH2Cl2) to give 6.00 g (67percent) of the product 388 as a brown oil. MS m/e: 287 (M+H). For n=2: MS m/e: 301 (M+H)
65% With pyridine In ethanol for 24 h; Inert atmosphere; Reflux Ethyl bromopyruvate (1.75 mL, 14.0 mmol) and pyridine (1.69 mL, 21.0 mmol) were added to a solution of 8 (1.33 g, 7.0 mmol) in dry EtOH (60 mL) under N2 atmosphere. The reaction mixture was refluxed 24 hs. The volatile components were removed in vacuo. The resulting residue was dissolved in EtOAc (40 mL), washed with water (30 mL) and brine (30 mL). The organic layer was dried with MgSO4, filtered and concentrated in vacuo. Purification by column chromatography afforded 5 (1.31g, 65percent) as a brown solid. Rf = 0.5 (hexane/ EtOAc, 1:1); 1H NMR (400MHz, CDCl3) δ 1.39 (t, 3H, J = 7,1 Hz), 1.46 (s, 9H), 4.14 (q, 2H, J = 7.1 Hz), 4.64 (d, 2H, J = 6.3 Hz), 5.31 (bs, 1H), 8.11 (s, 1H5). 13C NMR (100MHz, CDCl3) δ 14.3, 28.3 (3C), 42.4, 61.5, 80.5, 127.9, 146.9, 155.6, 161.3, 170.0.

Reference: [1] Tetrahedron, 1988, vol. 44, # 18, p. 5833 - 5844
[2] Synlett, 2008, # 15, p. 2379 - 2383
[3] Patent: US6642388, 2003, B1, . Location in patent: Page/Page column 9
[4] Tetrahedron, 2018, vol. 74, # 5, p. 549 - 555
[5] Patent: CN103601742, 2016, B, . Location in patent: Paragraph 0124-0126
[6] Patent: US6642388, 2003, B1, . Location in patent: Page/Page column 9
[7] Tetrahedron, 1986, vol. 42, # 10, p. 2695 - 2702
[8] Journal of Organic Chemistry, 1985, vol. 50, # 15, p. 2787 - 2788
[9] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 16, p. 3475 - 3485
[10] Journal of the American Chemical Society, 2016, vol. 138, # 16, p. 5426 - 5432
[11] Patent: WO2017/132459, 2017, A1, . Location in patent: Page/Page column 105-106
[12] Organic Process Research and Development, 2018, vol. 22, # 2, p. 190 - 199
[13] Journal of Asian Natural Products Research, 2010, vol. 12, # 11, p. 940 - 949
[14] Patent: WO2005/121130, 2005, A2, . Location in patent: Page/Page column 392
[15] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4994 - 4997
[16] Organic Letters, 2011, vol. 13, # 4, p. 680 - 683
[17] Journal of the American Chemical Society, 2002, vol. 124, # 38, p. 11272 - 11273
[18] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 834 - 864
[19] Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 8, p. 2309 - 2316
[20] Patent: US6642388, 2003, B1, . Location in patent: Page/Page column 8
[21] Patent: US6344562, 2002, B1, . Location in patent: Page column 53
[22] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 1, p. 132 - 136
[23] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 4, p. 401 - 406
  • 2
  • [ 35150-09-5 ]
  • [ 96929-05-4 ]
Reference: [1] Journal of the American Chemical Society, 2002, vol. 124, # 38, p. 11272 - 11273
[2] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 3, p. 601 - 607
[3] Journal of Organic Chemistry, 1985, vol. 50, # 15, p. 2787 - 2788
[4] Tetrahedron, 1986, vol. 42, # 10, p. 2695 - 2702
[5] Organic Letters, 2011, vol. 13, # 4, p. 680 - 683
[6] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4994 - 4997
[7] Patent: CN103601742, 2016, B,
[8] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 4, p. 401 - 406
[9] Tetrahedron, 2018, vol. 74, # 5, p. 549 - 555
[10] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 834 - 864
[11] Patent: WO2005/121130, 2005, A2,
  • 3
  • [ 4530-20-5 ]
  • [ 96929-05-4 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 3, p. 601 - 607
[2] Patent: US5998470, 1999, A,
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4994 - 4997
[4] Patent: CN103601742, 2016, B,
[5] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 4, p. 401 - 406
[6] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 834 - 864
  • 4
  • [ 24424-99-5 ]
  • [ 96929-05-4 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 15, p. 2787 - 2788
[2] Tetrahedron, 1986, vol. 42, # 10, p. 2695 - 2702
[3] Tetrahedron, 1988, vol. 44, # 18, p. 5833 - 5844
[4] Tetrahedron, 2018, vol. 74, # 5, p. 549 - 555
[5] Patent: WO2005/121130, 2005, A2,
  • 5
  • [ 4530-20-5 ]
  • [ 70-23-5 ]
  • [ 543-27-1 ]
  • [ 96929-05-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 19, p. 7672 - 7680
  • 6
  • [ 85363-04-8 ]
  • [ 96929-05-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 16, p. 3475 - 3485
[2] Tetrahedron, 1988, vol. 44, # 18, p. 5833 - 5844
  • 7
  • [ 31954-27-5 ]
  • [ 96929-05-4 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 4, p. 401 - 406
  • 8
  • [ 67-56-1 ]
  • [ 868-59-7 ]
  • [ 85363-04-8 ]
  • [ 297165-32-3 ]
  • [ 96929-05-4 ]
Reference: [1] Organic Process Research and Development, 2018, vol. 22, # 2, p. 190 - 199
  • 9
  • [ 89226-13-1 ]
  • [ 96929-05-4 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 3, p. 601 - 607
  • 10
  • [ 95104-84-0 ]
  • [ 96929-05-4 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 3, p. 601 - 607
  • 11
  • [ 4530-20-5 ]
  • [ 70-23-5 ]
  • [ 17341-93-4 ]
  • [ 96929-05-4 ]
Reference: [1] MedChemComm, 2014, vol. 5, # 9, p. 1309 - 1316
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