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[ CAS No. 29182-42-1 ] {[proInfo.proName]}

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Chemical Structure| 29182-42-1
Chemical Structure| 29182-42-1
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Product Details of [ 29182-42-1 ]

CAS No. :29182-42-1 MDL No. :MFCD00546397
Formula : C11H11NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :VYMJUZXFYAREJY-UHFFFAOYSA-N
M.W : 221.28 Pubchem ID :359796
Synonyms :

Calculated chemistry of [ 29182-42-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.27
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 60.29
TPSA : 67.43 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.19
Log Po/w (XLOGP3) : 2.57
Log Po/w (WLOGP) : 2.4
Log Po/w (MLOGP) : 1.67
Log Po/w (SILICOS-IT) : 3.64
Consensus Log Po/w : 2.5

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.01
Solubility : 0.216 mg/ml ; 0.000975 mol/l
Class : Soluble
Log S (Ali) : -3.63
Solubility : 0.0514 mg/ml ; 0.000232 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.86
Solubility : 0.0303 mg/ml ; 0.000137 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.52

Safety of [ 29182-42-1 ]

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 [ 29182-42-1 ]

* 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 [ 29182-42-1 ]
  • Downstream synthetic route of [ 29182-42-1 ]

[ 29182-42-1 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 29182-42-1 ]
  • [ 42182-65-0 ]
Reference: [1] Helvetica Chimica Acta, 1970, vol. 53, p. 1683 - 1693
  • 2
  • [ 105-56-6 ]
  • [ 137-07-5 ]
  • [ 29182-42-1 ]
YieldReaction ConditionsOperation in experiment
90% at 120℃; for 3 h; To a mixture of o-aminothiophenol (5 g, 39.9 mmol) was added ethyl cyanoacetate (4.25 ml, 39.9 mmol)The reaction was carried out at 120 ° C for 3 hours with stirring,Concentrated under reduced pressure,To give 8 g of ethyl 2- (2-benzothiazole) acetate,As a brown oil,Yield 90percent.
72% at 120℃; for 3 h; Example 1
Ethyl 2-(benzothiazol-2-yl)acetate was prepared by the method of Abbotto, Bradamante et. al. (J. Org. Chem. 2002, 16, 5753).
A neat mixture of 2-aminothiophenol (6.94 g, 50 mmol) and ethyl cyanoacetate (5.65 g, 50 mmol) was heated at 120° C. for 3 hours at which time TLC analysis indicated that the reaction was complete as judged by the disappearance of starting material.
The dark orange mixture was diluted with ethyl acetate/hexanes and purified by flash chromatography using 10-20percent ethyl acetate/hexanes (Rf0.35, 10percent ethyl acetate/hexanes) as an eluant.
After concentration by rotary evaporator, ethyl 2-(benzothiazol-2-yl)acetate could be obtained as a yellow oil in 72percent yield (7.97 g). LCMS: 222.3 (M+H)+.
65% at 120℃; 2-aminothiophenol 4 (1.0 eq, 20.0 g, 160 mmol) and ethyl cyanoacetate 5 (4.0 eq, 60 ml, 639 mmol) were stirred at 120° overnight. The reaction mixture was poured on silica gel and eluted with a 1:9 mixture of AcOEt and hexanes. The material was purified a second time by flash chromatography on silica gel (2.5 to 10percent gradient of AcOEt in hexanes) to afford a yellow viscous oil (22.6 g, 65percent yield). LCMS (ES): 95percent pure, m/z 222 [M+1]+.
40% at 120℃; [00389] Intermediate 28a: Ethyl 2-(1,3-benzothiazol-2-yI)acetate[00390] 2-Aminothiophenol (1 .OOg, 7.ggmmol) and ethyl cyanoacetate (3.4OmL, 31 .gSmmol) were heated at 120 °C overnight. After cooling to room temperature the mixture was subjected directly tocolumn chromatography eluting with 0 to 20percent EtOAc in heptane) to give ethyl 2-(1 ,3-benzothiazol-2-yl)acetate (704mg, 3.l8mmol, 40percent yield) as a bright orange oil.1H NMR (CDCI3, 400MHz) O/ppm: 8.05 (1H, d, J= 8.4Hz), 7.91 (1H, d, J= 8.0Hz), 7.53 (1H, m),7.43 (1H, m), 4.28 (2H, q, J= 7.2Hz), 4.23 (2H, 5), 1.33 (3H, t, J= 7.2Hz).MS Method 2: RT: 1.61 mi m/z 222.1 [M+H]

Reference: [1] Patent: CN104177379, 2016, B, . Location in patent: Paragraph 0050; 0052; 0053
[2] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 5, p. 1461 - 1462
[3] Patent: US2007/32652, 2007, A1, . Location in patent: Page/Page column 20-21
[4] Patent: US2011/112086, 2011, A1, . Location in patent: Page/Page column 16
[5] Journal of the American Chemical Society, 2010, vol. 132, # 4, p. 1276 - 1288
[6] Patent: WO2016/51193, 2016, A1, . Location in patent: Paragraph 00388; 00389; 00390
[7] Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5753 - 5772
[8] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 866 - 876
  • 3
  • [ 2318-25-4 ]
  • [ 137-07-5 ]
  • [ 29182-42-1 ]
YieldReaction ConditionsOperation in experiment
54% at 70℃; for 16 h; Part 1 : Preparation of ethyl 2-(benzo[d]thiazol-2-yl)acetate 16 h [00577] A mixture of 2-aminobenzenethiol (5.34 mL, 50 mmol) and 3-ethoxy-3- iminopropanoate hydrochloride (9.75 g, 50 mmol) in EtOH (50 mL) was heated at 70 °C for 16 h. The mixture was partitioned in EtO Ac (200 mL) and water (200 mL). The organic layer was washed with brine, dried over MgS04, filtered and concentrated. The residue was purified by silica gel column chromatography (10percent EtO Ac in hexanes) to give the title compound (6.0 g, 54percent) as a yellow oil. MS m/z 222.1 [M+H]+; 1H NMR (500 MHz, DMSO- 6): δ 8.05 (1H, d, J = 8.1 Hz), 7.91 (1H, d, J= 8.0 Hz), 7.51 (1H, t, J= 8 Hz), 7.43 (1H, t, J= 8 Hz), 4.28 (2H, q, J = 7.2 Hz), 4.22 (2H, s), 1.33 (3H, t, J= 7.1 Hz).
54% at 70℃; for 16 h; Part 1:
Preparation of ethyl 2-(benzo[d]thiazol-2-yl)acetate
A mixture of 2-aminobenzenethiol (5.34 mL, 50 mmol) and 3-ethoxy-3-iminopropanoate hydrochloride (9.75 g, 50 mmol) in EtOH (50 mL) was heated at 70° C. for 16 h.
The mixture was partitioned in EtOAc (200 mL) and water (200 mL).
The organic layer was washed with brine, dried over MgSO4, filtered and concentrated.
The residue was purified by silica gel column chromatography (10percent EtOAc in hexanes) to give the title compound (6.0 g, 54percent) as a yellow oil. MS m/z 222.1 [M+H]+; 1H NMR (500 MHz, DMSO-d6): δ 8.05 (1H, d, J=8.1 Hz), 7.91 (1H, d, J=8.0 Hz), 7.51 (1H, t, J=8 Hz), 7.43 (1H, t, J=8 Hz), 4.28 (2H, q, J=7.2 Hz), 4.22 (2H, s), 1.33 (3H, t, J=7.1 Hz).
Reference: [1] Russian Journal of General Chemistry, 2001, vol. 71, # 7, p. 1076 - 1087
[2] Patent: WO2013/101974, 2013, A1, . Location in patent: Paragraph 00574; 00575; 00576; 00577
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 13, p. 6070 - 6085
[4] Patent: US9617268, 2017, B2, . Location in patent: Page/Page column 319
  • 4
  • [ 137-07-5 ]
  • [ 105-53-3 ]
  • [ 29182-42-1 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 84, p. 12470 - 12473
[2] European Journal of Medicinal Chemistry, 1992, vol. 27, # 1, p. 39 - 44
[3] Journal of the American Chemical Society, 2010, vol. 132, # 41, p. 14391 - 14393
  • 5
  • [ 880883-60-3 ]
  • [ 29182-42-1 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 18, p. 3687 - 3689
  • 6
  • [ 137-07-5 ]
  • [ 36239-09-5 ]
  • [ 29182-42-1 ]
Reference: [1] Helvetica Chimica Acta, 1970, vol. 53, p. 1683 - 1693
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 6, p. 3408 - 3418
  • 7
  • [ 56278-50-3 ]
  • [ 64-17-5 ]
  • [ 29182-42-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4596 - 4607
  • 8
  • [ 137-07-5 ]
  • [ 105-53-3 ]
  • [ 29182-42-1 ]
  • [ 1945-78-4 ]
Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, p. 2339 - 2344
  • 9
  • [ 137-07-5 ]
  • [ 36239-09-5 ]
  • [ 29182-42-1 ]
  • [ 28731-96-6 ]
Reference: [1] Helvetica Chimica Acta, 1970, vol. 53, p. 1683 - 1693
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