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[ CAS No. 40283-46-3 ] {[proInfo.proName]}

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Chemical Structure| 40283-46-3
Chemical Structure| 40283-46-3
Structure of 40283-46-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 40283-46-3 ]

CAS No. :40283-46-3 MDL No. :MFCD06203554
Formula : C4H4N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :ZFMRDDYYJJCBKC-UHFFFAOYSA-N
M.W : 144.15 Pubchem ID :315243
Synonyms :

Calculated chemistry of [ 40283-46-3 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 33.48
TPSA : 104.45 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.54
Log Po/w (XLOGP3) : 0.47
Log Po/w (WLOGP) : 0.43
Log Po/w (MLOGP) : -0.95
Log Po/w (SILICOS-IT) : 0.87
Consensus Log Po/w : 0.27

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.37
Solubility : 6.08 mg/ml ; 0.0422 mol/l
Class : Very soluble
Log S (Ali) : -2.23
Solubility : 0.844 mg/ml ; 0.00586 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.28
Solubility : 74.8 mg/ml ; 0.519 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.21

Safety of [ 40283-46-3 ]

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 [ 40283-46-3 ]

* 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 [ 40283-46-3 ]
  • Downstream synthetic route of [ 40283-46-3 ]

[ 40283-46-3 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 32955-21-8 ]
  • [ 40283-46-3 ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydroxide In tetrahydrofuran; waterReflux To the solution of the thiazole ethyl ester (0.80 g, 4.32 mmol) in THF/water (2:1), NaOH was added (0.65 g, 16.3 mmol), and the reaction mixture was refluxed overnight. THF was removed under reduced pressure and afterward the reaction mixture was neutralized with 1 M HCl. The resulting precipitate 1 was filtered, washed with diethyl ether and dried overnight at 60 °C. Yield: 86percent;off-white crystals, mp 168-171 C (lit. [32] 172e173 °C). 1H NMR(400 MHz, DMSO-d6): d 7.81 (s, 1H, oxazol-H), 8.99 (br s, 2H, NH2)ppm. HRMS (ESI): m/z [M H] calcd for C4H5N2O2S 145.1475;found 145.1502.
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 67, p. 208 - 220
[2] Recueil des Travaux Chimiques des Pays-Bas, 1944, vol. 63, p. 226
[3] Yakugaku Zasshi, 1948, vol. 68, p. 101[4] Chem.Abstr., 1953, p. 7452
[5] Chemische Berichte, 1943, vol. 76, p. 419,428
[6] Journal of Medicinal Chemistry, 1972, vol. 15, p. 1310 - 1312
  • 2
  • [ 6633-61-0 ]
  • [ 40283-46-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991, # 3, p. 349 - 352
  • 3
  • [ 99903-61-4 ]
  • [ 40283-46-3 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1944, vol. 63, p. 226
  • 4
  • [ 40283-46-3 ]
  • [ 24424-99-5 ]
  • [ 302964-02-9 ]
Reference: [1] Patent: WO2012/51450, 2012, A1, . Location in patent: Page/Page column 27
  • 5
  • [ 40283-46-3 ]
  • [ 64588-82-5 ]
YieldReaction ConditionsOperation in experiment
31.6%
Stage #1: With potassium hydrogencarbonate In 1,4-dioxane; methanol; water; toluene at 20℃; for 2 h;
Stage #2: With 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate In 1,4-dioxane; methanol; water; toluene at 20℃; for 1 h;
Synthesis of 5-Fluoro-thiazol-2-ylamine2-Amino-thiazole-5-carboxylic acid (2.16 g, 15 mmol) and KHCO3 (5.25 g, 52.5 mmol) were suspended in a mixture of water (7 ml), methanol (30 ml), dioxane (42 ml) and Toluene (42 ml). This was stirred at room temperature for 2 hours. Next, F-TEDA (9.3 g, 26.25 mmol) was added to the reaction vessel. This mixture was allowed to stir at room temperature for 1 hour. After this period, the reaction mixture was filtered and the filtrate was concentrated in vacuo to afford a dark residue. This material was purified by silica flash chromatography (DCM:THF, 8:2) to afford the product, 5-Fluoro-thiazol-2-ylamine (560 mg, 31.6percent).
Reference: [1] Patent: WO2011/115758, 2011, A1, . Location in patent: Page/Page column 13
  • 6
  • [ 40283-46-3 ]
  • [ 745053-64-9 ]
YieldReaction ConditionsOperation in experiment
69%
Stage #1: With potassium phosphate In 1,4-dioxane; methanol; toluene at 20℃; for 2 h;
Stage #2: With 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate In 1,4-dioxane; methanol; toluene at 20℃; for 0.5 h;
Stage #3: With hydrogenchloride In 1,4-dioxane; methanol; toluene
2-Amino-thiazole-5-carboxylic acid (8.64 g, 60 mmol) and K3P04 (13.04 g, 90 mmol) were suspended in a mixture of methanol (100 ml), dioxane (150 ml) and toluene (150 ml). This was stirred at room temperature for 2 hours. Next, F-TEDA (34.5 g, 97 mmol) was added to the reaction vessel. This mixture was allowed to stir at room temperature for 30 minutes. After this period, the reaction mixture was filtered through a silica gel plug, acidified with HC1 in dioxane, concentrated in vacuo and lyophilized for 12 hours to afford the product, 5-Fluoro-thiazol-2-ylamine HC1 salt (6.42 g, 69percent).
Reference: [1] Patent: WO2011/115758, 2011, A1, . Location in patent: Page/Page column 13-14
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