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[ CAS No. 859522-19-3 ] {[proInfo.proName]}

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Chemical Structure| 859522-19-3
Chemical Structure| 859522-19-3
Structure of 859522-19-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 859522-19-3 ]

CAS No. :859522-19-3 MDL No. :MFCD09702004
Formula : C7H10N2O2S2 Boiling Point : -
Linear Structure Formula :- InChI Key :QRIYTBYTQBRMNL-UHFFFAOYSA-N
M.W : 218.30 Pubchem ID :21455623
Synonyms :

Calculated chemistry of [ 859522-19-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.43
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.95
TPSA : 118.75 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.92
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 1.39
Log Po/w (MLOGP) : 0.19
Log Po/w (SILICOS-IT) : 1.96
Consensus Log Po/w : 1.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.24
Solubility : 1.24 mg/ml ; 0.0057 mol/l
Class : Soluble
Log S (Ali) : -3.85
Solubility : 0.0308 mg/ml ; 0.000141 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.94
Solubility : 2.51 mg/ml ; 0.0115 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.92

Safety of [ 859522-19-3 ]

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 [ 859522-19-3 ]

* 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 [ 859522-19-3 ]
  • Downstream synthetic route of [ 859522-19-3 ]

[ 859522-19-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 61296-22-8 ]
  • [ 623-51-8 ]
  • [ 859522-19-3 ]
YieldReaction ConditionsOperation in experiment
54% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2 h; (2-Aminothiazol-5-ylsulfanyl)-acetic acid ethyl ester:; A mixture of 2-amino- 5-bromothiazole, HBr (7.26 g, 27.9 mmol), ethyl thioglycolate (1 O g, 83.8 mmol), and potassium carbonate (7.7 g, 55.9 mmol) in DMF (25 ml_) was stirred at room temperature for 2 hours. The reaction mixture was filtered and water (150 ml_) and ethyl acetate (400 ml_) were added. The organic phase was isolated and washed with brine (3 x 50 ml_), dried over anhydrous magnesium sulphate, and evaporated to dryness in vacuo to give (2-aminothiazol-5-ylsulfanyl)-acetic acid ethyl ester. Yield: 3.3 g (54 percent). 1H-NMR (DMSO-d6): δ 7.6 (s, 2H), 7.00 (s, 1 H)1 4.08 (q, 2H), 3.45 (s, 2H), 1.17 (t, 3H).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 9, p. 2063 - 2068
[2] Patent: WO2006/58923, 2006, A1, . Location in patent: Page/Page column 51
  • 2
  • [ 3034-22-8 ]
  • [ 623-51-8 ]
  • [ 859522-19-3 ]
YieldReaction ConditionsOperation in experiment
54% With hydrogen bromide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2 h; (2-Aminothiazol-5-ylsulfanyl)-acetic acid ethyl ester: A mixture of 2-amino-5-bromothiazole, HBr (7.26 g, 27.9 mmol), ethyl thioglycolate (10 g, 83.8 mmol), and potassium carbonate (7.7 g, 55.9 mmol) in DMF (25 mL) was stirred at room temperature for 2 hours. The reaction mixture was filtered and water (150 mL) and ethyl acetate (400 mL) were added. The organic phase was isolated and washed with brine (3.x.50 mL), dried over anhydrous magnesium sulphate, and evaporated to dryness in vacuo to give (2-aminothiazol-5-ylsulfanyl)-acetic acid ethyl ester. Yield: 3.3 g (54percent). 1H-NMR (DMSO-d6): δ 7.6 (s, 2H), 7.00 (s, 1H), 4.08 (q, 2H), 3.45 (s, 2H), 1.17 (t, 3H).
50%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 13.1667 - 16.1667 h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate; N,N-dimethyl-formamide
Coupling: Preparation of: (2-aminothiazol-5-ylsulfanyl) acetic acid ethyl ester5-Bromo-2-aminothiazole (25 g, 96 mmol) and K2CO3 (26.5 g, 192 mmol) was suspended in DMF (50 ml_) and stirred to 0 0C. Ethyl thioglycolate (11 .6 ml_, 96 mmol) was added during 10 min. The reaction mixture was allowed to reach room temperature and stirred for further 16 h. Addition of water (100 ml_) and EtOAc (150 ml_). Separation of the organic phase fol- lowed by extraction of the aqueous phase with EtOAc (2x100 ml_).The combined organic phases were washed with aqueous NaHCO3 (2000 ml_), brine (2x200 ml_) and dried (MgSO4), filtered and evaporated. The crude product was dissolved in a small amount of DCM and purified by flash chromathography (ISCO 330 g silica column, eluent A: heptane / B: 2percent TEA in EtOAc. Gradient from 30percent B ->100percent B.) to give 50-65percent pure (2-aminothiazol- 5-ylsulfanyl) acetic acid ethyl ester as a dark red-brown oil.1H NMR (CDCI3): J7.16 (s, 1 H), 5.45 (bs, 2H), 4.26 (q, 2H), 3.39 (s, 2H), 1 .28 (t, 3H); Example 152 {2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acidPreparation of (2-aminothiazol-5-ylsulfanyl) acetic acid ethyl ester:5-Bromo-2-aminothiazole (25 g, 96 mmol) and K2CO3 (26.5 g, 192 mmol) was suspended in DMF (50 ml_) and stirred to 0 0C. Ethyl thioglycolate (11 .6 ml_, 96 mmol) was added during 10 min. The reaction mixture was allowed to reach room temperature and stirred for further 13H. Addition of water (100 ml_) and EtOAc (150 ml_). Separation of the organic phase fol- lowed by extraction of the aqueous phase with EtOAc (2x100 ml_).The combined organic phases were washed with aqueous NaHCO3 (2000 ml_), brine (2x200 ml_) and dried (MgSO4), filtered and evaporated. The crude product was dissolved in a small amount of DCM and purified by flash chromathography (ISCO 330 g silica column, eluent A: heptane / B: 2percent TEA in EtOAc. Gradient from 30percent B ->100percent B.) to give 50-65percent pure (2-aminothiazol- 5-ylsulfanyl) acetic acid ethyl ester as a dark red-brown oil.1H NMR (CDCI3): .pound.7.16 (s, 1 H), 5.45 (bs, 2H), 4.26 (q, 2H), 3.39 (s, 2H), 1 .28 (t, 3H).
Reference: [1] Patent: US2008/139562, 2008, A1, . Location in patent: Page/Page column 15
[2] Patent: WO2007/6814, 2007, A1, . Location in patent: Page/Page column 78-79; 155
[3] Patent: WO2008/84043, 2008, A1, . Location in patent: Page/Page column 44-45
[4] Patent: WO2008/84044, 2008, A1, . Location in patent: Page/Page column 59-60
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