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[ CAS No. 1918-78-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1918-78-1
Chemical Structure| 1918-78-1
Chemical Structure| 1918-78-1
Structure of 1918-78-1 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 1918-78-1 ]

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Product Details of [ 1918-78-1 ]

CAS No. :1918-78-1 MDL No. :MFCD01859891
Formula : C6H6O2S Boiling Point : -
Linear Structure Formula :- InChI Key :YJZOPBSZDIBXBG-UHFFFAOYSA-N
M.W : 142.18 Pubchem ID :4625409
Synonyms :

Calculated chemistry of [ 1918-78-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.24
TPSA : 65.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.94
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 0.9
Log Po/w (SILICOS-IT) : 2.34
Consensus Log Po/w : 1.49

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.33 mg/ml ; 0.00932 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.434 mg/ml ; 0.00305 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.4
Solubility : 5.63 mg/ml ; 0.0396 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.04

Safety of [ 1918-78-1 ]

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 [ 1918-78-1 ]

* 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 [ 1918-78-1 ]
  • Downstream synthetic route of [ 1918-78-1 ]

[ 1918-78-1 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 88-13-1 ]
  • [ 74-88-4 ]
  • [ 1918-78-1 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran for 1 h;
Stage #2: for 1 h;
Compound 9 was synthesized as reported previously [24]. To a solution of diisopropylamine (233g, 2.30mol) in THF (2.3L), a solution of n-BuLi (1.6M in n-hexane, 1.50L, 2.40mol) was added dropwise at 0°C. After stirring at the same temperature for 40min, the reaction mixture was cooled to−60°C, compound 8 (223g, 1.74mol) in THF (500mL) added dropwise, and stirred at the same temperature for 1h. After the addition of MeI (254g, 1.79mol), the reaction mixture was allowed to warm to room temperature and stirred for 1h. Next, the mixture was concentrated under reduced pressure, acidified with 6N aqueous HCl (to pH 1), and extracted with AcOEt. The organic layer was washed with brine and dried over Na2SO4. After filtration, the solvent was concentrated under reduced pressure and the residue was crystallized with H2O/AcOH to give 209g (85percent) of 9 as a pale-yellow solid: 1H NMR (400MHz, CDCl3) δ 7.45 (d, J=5.4Hz, 1H), 7.01 (d, J=5.4Hz, 1H), 2.78 (s, 3H); MS (ESI) m/z: 143 (M+H)+, 141 (M−H).
82.1%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 2 h;
1 (15.00 g, 0.12 mol) was dissolved in THF (50ml). Under argon protection, n-butyl lithium (2.0 M THF solution, 120 ml) wasadded dropwise at -78 °C. The reaction mixture was stirred for 1 h at -78 °C.To this mixture was added CH3I (8.7 ml, 0.14 mol), then the reactionmixture was allowed to warm to room temperature and stirred for 2 hours. Slowlyquenched the reaction with hydrogen chloride (2.0 M ethyl acetate solution), thenstirred the mixture at room temperature for 30 min before concentrating in vacuo. The residue was diluted with H2O(100 ml) and extracted with ethyl acetate (200 ml). The combined organic layerswere washed with H2O (50 ml ×2) and brine (50 ml ×2), dried overanhydrous Na2SO4, and filtrated, then the solvent wasevaporated under reduced pressure to give a yellow crude solid, which waspurified by recrystallization from acetic acid/H2O to afford 2 (14.00 g, 82.1percent ) as a white solid:mp 108-110 °C. 1H NMR (400 MHz, CDCl3)δ 7.45 (d, J = 5.5 Hz, 1H), 7.01 (d, J = 5.5, 1H), 2.73 (s, 3H). MS (EI) m/z: 142 (M+).
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5417 - 5422
[2] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 269 - 294
[3] European Journal of Medicinal Chemistry, 2015, vol. 102, p. 471 - 476
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, p. 791 - 794
[5] Patent: US6340759, 2002, B1, . Location in patent: Example 290
[6] Patent: US2012/101137, 2012, A1, . Location in patent: Page/Page column 14
  • 2
  • [ 74-88-4 ]
  • [ 1918-78-1 ]
YieldReaction ConditionsOperation in experiment
20%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 1.16667 h;
Stage #2: at -78 - 20℃; for 1 h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane
EXAMPLE 27; Preparation of 2-Amino-5-(2-methylthien-3-yl)-3-methyl-5-(3-pyrimidin-5-ylphenyl)-3,5-dihydro-4H-imidazol-4-one; Step a); Preparation of Compound 19; A solution of diisopropylamine (8.28 g, 81.8 mmol) in THF (190 mL) at -20° C. was treated with n-butyllithium (52 mL of a 1.6 M solution in hexanes, 83.2 mmol) over a period of 20 min, then slowly warmed to 0° C. under stirring for 30 min. This solution was cooled to -78° C. and treated dropwise with a solution of thiophene-3-carboxylic acid (4.99 g, 38.9 mmol) in THF (40 mL) over a period of 10 min. The mixture was stirred at -78° C. for an additional 10 min, then treated with iodomethane (6.16 g, 43.3 mmol) and stirred for 1 h, allowing the solution to slowly warm to rt. Water (200 mL) was added, and the mixture was made acidic by adding 2 N HCl (40 mL). The layers were separated and the aqueous layer was extracted with ether (3.x.75 mL), then the combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography (silica, 50:50:1 ethyl acetate/hexanes/acetic acid) afforded 19 (1.12 g, 20percent) as a white solid: 1H NMR (500 MHz, CDCl3) δ 7.45 (d, J=5.4 Hz, 1H), 7.01 (t, J=5.4 Hz, 1H), 2.77 (s, 3H).
Reference: [1] Patent: US2007/4786, 2007, A1, . Location in patent: Page/Page column 18-19
  • 3
  • [ 60-29-7 ]
  • [ 88-13-1 ]
  • [ 74-88-4 ]
  • [ 1918-78-1 ]
Reference: [1] Patent: US5475022, 1995, A,
  • 4
  • [ 19432-66-7 ]
  • [ 1918-78-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2004, vol. 2, # 21, p. 3119 - 3127
  • 5
  • [ 30319-05-2 ]
  • [ 124-38-9 ]
  • [ 1918-78-1 ]
Reference: [1] Synthetic Communications, 2013, vol. 43, # 5, p. 681 - 688
  • 6
  • [ 109-72-8 ]
  • [ 88-13-1 ]
  • [ 74-88-4 ]
  • [ 1918-78-1 ]
Reference: [1] Patent: US5840917, 1998, A,
  • 7
  • [ 765-50-4 ]
  • [ 541-41-3 ]
  • [ 1918-78-1 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 3934,3937
  • 8
  • [ 765-50-4 ]
  • [ 1918-78-1 ]
  • [ 1918-77-0 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 3934,3937
  • 9
  • [ 88-13-1 ]
  • [ 1918-78-1 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, # 52, p. 5051 - 5054
  • 10
  • [ 30319-05-2 ]
  • [ 1918-78-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1935, vol. 515, p. 273,277
  • 11
  • [ 74-88-4 ]
  • [ 1918-78-1 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, # 52, p. 5051 - 5054
[2] Tetrahedron Letters, 1980, vol. 21, # 52, p. 5051 - 5054
  • 12
  • [ 19432-64-5 ]
  • [ 15719-64-9 ]
  • [ 1918-78-1 ]
  • [ 1918-77-0 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 3934,3937
  • 13
  • [ 765-50-4 ]
  • [ 1918-78-1 ]
  • [ 1918-77-0 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 3934,3937
  • 14
  • [ 19432-64-5 ]
  • [ 15719-64-9 ]
  • [ 1918-78-1 ]
  • [ 1918-77-0 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 3934,3937
  • 15
  • [ 67-56-1 ]
  • [ 1918-78-1 ]
  • [ 53562-51-9 ]
YieldReaction ConditionsOperation in experiment
96% for 3 h; Reflux Thionyl chloride (200mL, 2.76mol) was slowly added dropwise to a solution of 9 (100g, 703mmol) in MeOH (500mL). After stirring at reflux for 3h, the mixture was concentrated under reduced pressure. The residue was diluted with CH2Cl2, washed with water, saturated aqueous NaHCO3 and brine, and dried over Na2SO4. After filtration, the solvent was concentrated under reduced pressure to give 105g (96percent) of 10 as a brown oil: 1H NMR (400MHz, CDCl3) δ 7.38 (d, J=5.4Hz, 1H), 6.98 (d, J=5.4Hz, 1H), 3.85 (s, 3H), 2.74 (s, 3H); MS (ESI) m/z: 157 (M+H)+.
78% at 0℃; for 4 h; Reflux 2 (14.00 g, 98.60 mmol) was dissolved inmethanol (60 ml). Concentrated sulfuric acid (30 ml) was added dropwise at 0°C. The reaction mixture was stirred for 4 h at reflux, thenwas cooled to room temperature, and the solvent was evaporated under reducedpressure. The residue was partitioned between CH2Cl2 (200 ml)and H2O (60 ml). The organic phase was washed with H2O (50 ml), saturated aqueous sodium bicarbonate solution (50ml) and saturated brine solution (50 ml),dried over Na2SO4, and filtrated, then the solvent wasevaporated under reduced pressure to give 3 (12.00 g, 78.0percent) as acolorless viscous oil. 1H NMR (400 MHz,CDCl3)δ 7.38 (d, J =5.5 Hz, 1H), 6.98 (d, J = 5.1, 1H), 3.85 (s, 3H), 2.73(s, 3H). MS (EI)m/z: 156 (M+).
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 269 - 294
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5417 - 5422
[3] European Journal of Medicinal Chemistry, 2015, vol. 102, p. 471 - 476
[4] Journal of Medicinal Chemistry, 1995, vol. 38, # 24, p. 4806 - 4820
[5] Patent: US2012/101137, 2012, A1, . Location in patent: Page/Page column 14
  • 16
  • [ 1918-78-1 ]
  • [ 74-88-4 ]
  • [ 53562-51-9 ]
Reference: [1] Patent: US5475022, 1995, A,
  • 17
  • [ 1918-78-1 ]
  • [ 74-88-4 ]
  • [ 53562-51-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, # 4, p. 1085 - 1087
  • 18
  • [ 1918-78-1 ]
  • [ 172292-52-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 24, p. 4806 - 4820
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