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Chemical Structure| 30235-26-8
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Product Details of [ 30235-26-8 ]

CAS No. :30235-26-8 MDL No. :MFCD00460417
Formula : C8H7N3S Boiling Point : -
Linear Structure Formula :- InChI Key :BLKHMTAXNXLDJP-UHFFFAOYSA-N
M.W : 177.23 Pubchem ID :1092459
Synonyms :

Calculated chemistry of [ 30235-26-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.75
TPSA : 80.04 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) : -6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 1.23
Log Po/w (WLOGP) : 1.8
Log Po/w (MLOGP) : 0.13
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 1.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.33
Solubility : 0.837 mg/ml ; 0.00472 mol/l
Class : Soluble
Log S (Ali) : -2.51
Solubility : 0.55 mg/ml ; 0.0031 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.08
Solubility : 0.148 mg/ml ; 0.000838 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.4

Safety of [ 30235-26-8 ]

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 [ 30235-26-8 ]

* 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 [ 30235-26-8 ]
  • Downstream synthetic route of [ 30235-26-8 ]

[ 30235-26-8 ] Synthesis Path-Upstream   1~7

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YieldReaction ConditionsOperation in experiment
79.6% for 4 h; Reflux (0.01 mol) of? -bromo 2-pyridineethanone, 0.76 g (0.01 mol) of thiourea and 50 mL of ethanol were added to a 100 mL round bottom flask and refluxed for 4 h.After completion of the reaction, the ethanol solvent was distilled off under reduced pressure.Column chromatography was performed on DCM: MeOH: NH4OH (20: 1: 0.1, v / v = 50: 1: 0.1) as the mobile phase.The title compound was obtained as a white solid, 1.41 g, 79.6percent yield
67%
Stage #1: at 20℃; for 1 h;
Stage #2: With sodium hydroxide In water
To a solution of 2 (11.2 mmol) in 25 ml of ethanol at room temperature was added thiourea (13.4 mmol).The reaction mixture was stirred at room temperature for 1 hour, quenched with water and washed with dichloromethane. The aqueous phase was concentrated in vacuo to give a yellow solid HBr salt. The salt was then dissolved in minimal amount of water and 10percent NaOH added drop wise until a white precipitate 3 formed (approximately at pH 8).The precipitate was then filtered and dried.
55%
Stage #1: at 90℃; for 2 h;
Stage #2: With sodium hydroxide In water for 0.416667 h;
General procedure T. 4-Pyridin~3-yl-thiazol-2-ylamine To a solution of 2-bromo-l-pyridin-2-yl-ethanone (leqv, 10 g, 50.0 mmol) in ethanol (100 ml) was added thiourea (1.02eqv, 3.88 g, 51.0 mmol) and the reaction mixture heated to 900C for 2hrs. Cooling to room temperature led to precipitation of the crude HBr product salt which was collected by filtration and washed with acetone. The solid was dissolved in 2M NaOH (25 ml), shaken for 25 mins and the basic aqueous solution extracted with EtOAc (3 x 30 ml). The combined organic phase was evaporated at reduced pressure to afford the product (4.83 g, 55 percent, 27.3 mmol) as an off-white solid. LC/MS: 100percent MH+, m/z 178, Rt = 0.64 mins.; 4-Pyridin-3-yl-thiazol-2-ylamineFollowing general procedure T (to scale 30 mmol 2-bromo-l-pyridin-3-yl-ethanone) the title compound (2.023 g, 38percent, 11.43 mmol) was isolated as a pale brown powder. LC/MS: 100percent MH+, m/z 178, Rt = 1.10 mins.
Reference: [1] Patent: CN105820163, 2016, A, . Location in patent: Paragraph 0127 - 0129
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 2, p. 560 - 564
[3] Patent: WO2008/122787, 2008, A1, . Location in patent: Page/Page column 85
[4] Journal of Heterocyclic Chemistry, 1970, vol. 7, p. 1137 - 1141
[5] Journal of the Chinese Chemical Society, 2017, vol. 64, # 12, p. 1408 - 1416
[6] Applied Organometallic Chemistry, 2018, vol. 32, # 5,
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YieldReaction ConditionsOperation in experiment
90%
Stage #1: at 23℃; for 0.5 h; Inert atmosphere
Stage #2: Inert atmosphere; Alkaline conditions
A solution of thiourea (1.2 g, 15 mmol) in H2O (10 mL) was added to a solution of 2-bromoacetylpyridine hydrobromide (4.2 g, 15 mmol) in H2O (20 mL). The reaction mixture was stirred for 30 min at 23 °C. The crystalline product was collected by filtration. The solid was suspended in H2O (50 mL) and made alkaline by adding 7percent aqueous ammonium hydroxide. The product was isolated as a white solid (2.4 g, 90percent yield). 1H NMR (600 MHz, CDCl3) δ 5.05 (br s, 2H), 7.18 (ddd, J = 7.3, 4.7, 1.2 Hz, 1H), 7.31 (s, 1H), 7.71 (td, J = 7.6, 1.5 Hz, 1H), 7.88 (d, J = 7.9 Hz, 1H), 8.58 (d, J = 4.4 Hz, 1H); 13C NMR and HRMS matched the reported values. 40
89% at 90℃; for 3 h; 2-bromo-1-(pyridin-2-yl)ethanone hydrobromide (500 mg, 1.78 mmol) and thiourea (542 mg, 7.12 mmole, 4 eq) were stirred in ethanol at 90 °C for 3 hours and then cooled and concentrated. The residue was partitioned between ethyl acetate and saturated NaHCCb. The organic phase was washed with water and brine, and then concentrated. The light yellow solid obtained was triturated with methylene chloride and dried (280 mg, 89percent). NMR (300 MHz, CDCh): δ 8.59 (d, J= 4.4 Hz, 1H), 7.89 (d, J= 7.9 Hz, 1H), 7.72 (td, J= 7.9, 1.8 Hz, 1H), 7.31 (s, 1H), 7.22-6.94 (m, 1H); Calculated for C8H7N3S, +.
56% at 70℃; for 2 h; To 2-bromo-1-pyridin-2-yl-ethanone (1 g, 5mmol) in ethanol was added thiourea (340 mg, 5.1 mmol). The mixture was stirred at 70°C.The reaction was monitored via LC/MS. After 2 h, the reaction mixture was cooled to roomtemperature and precipitate was formed. The precipitate was collected by vacuum filtrationand washed with acetone. The solid was dissolved in 2MNaOH (25 mL) and extracted withEtOAc (3 x 50 mL). The combined organic layers were dried over Na2SO4 and concentrated invacuo to give 3 (497 mg, 56percent yield), as an off-white solid. 1H NMR: (300 MHz, CD3OD): δ7.24–7.31 (m, 2H), 7.80–7.92 (m, 2H), 8.49–8.51 (m, 1H); 13C NMR: (300 MHz, CD3OD): δ105.9, 120.8, 122.3, 137.3, 148.5, 149.5, 152.4; HRMS MS ESI m/z calcd for C8H7N3S (M+H)+178.0433, found 178.0441 (Δ 0.8 ppm). All data are consistent with literature values [19].
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6385 - 6397
[2] Patent: WO2018/13508, 2018, A1, . Location in patent: Paragraph 0168
[3] PLoS ONE, 2016, vol. 11, # 5,
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Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 39, p. 5265 - 5269
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  • [ 1122-62-9 ]
  • [ 17356-08-0 ]
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Reference: [1] MedChemComm, 2018, vol. 9, # 4, p. 685 - 696
[2] Chemische Berichte, 1959, vol. 92, p. 22,35
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 18, p. 5464 - 5468
  • 5
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 2, p. 560 - 564
[2] PLoS ONE, 2016, vol. 11, # 5,
[3] Journal of the Chinese Chemical Society, 2017, vol. 64, # 12, p. 1408 - 1416
  • 6
  • [ 100-69-6 ]
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Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 5, p. 1093 - 1101
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Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 5, p. 1093 - 1101
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