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[ CAS No. 17289-25-7 ] {[proInfo.proName]}

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Chemical Structure| 17289-25-7
Chemical Structure| 17289-25-7
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Product Details of [ 17289-25-7 ]

CAS No. :17289-25-7 MDL No. :MFCD06738905
Formula : C5H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :NLEAEGDBKRBJAP-UHFFFAOYSA-N
M.W : 112.13 Pubchem ID :7060524
Synonyms :

Calculated chemistry of [ 17289-25-7 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 29.62
TPSA : 38.05 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) : -7.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.9
Log Po/w (XLOGP3) : -0.84
Log Po/w (WLOGP) : -0.24
Log Po/w (MLOGP) : -0.94
Log Po/w (SILICOS-IT) : 0.19
Consensus Log Po/w : -0.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.4
Solubility : 44.4 mg/ml ; 0.396 mol/l
Class : Very soluble
Log S (Ali) : 0.52
Solubility : 373.0 mg/ml ; 3.32 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.57
Solubility : 30.4 mg/ml ; 0.271 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 17289-25-7 ]

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 [ 17289-25-7 ]

* 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 [ 17289-25-7 ]
  • Downstream synthetic route of [ 17289-25-7 ]

[ 17289-25-7 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 41716-18-1 ]
  • [ 17289-25-7 ]
YieldReaction ConditionsOperation in experiment
78.95% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 50℃; To a suspension of 1-methyl-imidazole-4-carboxylic acid [(11.] 4g, 90 [MMOL)] in THF (500ml) at [0°C,] was added dropwise lithium aluminium hydride (solution 1 M in THF, [117MOL,] 117 [MMOL)] and the mixture was stirred at room temperature overnight and then at [50°C] for 1 hour. Then water (3 mi) was added followed by [NA2S04,] and the resulting precipitate was filtered off on [A] [CELITE PAD. THE FILTRATE] was concentrated under reduced pressure to afford the title compound as a solid (8g, 78.95percent) ;'H NMR (300 MHz, CDCl3, ppm) [8] : 7.25 (s, [1 H),] 6.7 (s, [1H),] 5.25 (m, [1 H),] 4.4 (s, 2H), [3.] 45 (s, 3H).
78.95%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 50℃; for 1 h;
Stage #2: With water; sodium sulfate In tetrahydrofuran
To a suspension of [1-METHYL-IMIDAZOLE-4-CARBOXYLIC] acid [(11.] 4g, 90 [MMOL)] in THF (500ml) at [0°C WAS] added dropwise LiAIH4 (solution 1 M in THF, 117ml. 117 [MMOL)] and the mixture was stirred at room temperature overnight and then at [50°C] for 1 hour. On cooling, water (3 [ML)] was added followed by [NA2SO4,] and the resulting precipitate was filtered through a celite pad. The filtrate was concentrated under reduced pressure to afford the title compound as a solid (8g, 78.95percent) [; H] NMR (300 MHz, CDCl3) [] ppm: [7. 25] (s, [1 H),] 6.7 (s, [1 H),] 5.25 (m, [1 H),] 4.4 (s, 2H), 3.45 (s, 3H).
78.95% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 50℃; To a suspension of [1-METHYL-IMIDAZOLE-4-CARBOXYLIC ACID (11.] 4g, 90 [MMOL)] in THF (500ml) at [0°C,] was added drop-wise a solution of lithium aluminium hydride [(1 M] in THF, [117ML,] 117 [MMOL)] and the mixture was stirred at room temperature overnight and then at [50°C] for 1 hour Water (3 [ML)] was added followed by [NA2SO4] and the mixture was filtered through [CELITETM.] The filtrate was concentrated under reduced pressure to afford the title compound as a solid [(8G,] 78.95percent) ;'H NMR (300 MHz, [CDCI3)] 6 ppm: 7.25 (s, 1 H), 6. 7 (s, 1H), 5.25 (m, 1H), 4.4 (s, 2H), 3.45 (s, 3H).
47.5% With lithium aluminium tetrahydride In tetrahydrofuran at 50℃; for 12 h; Inert atmosphere 190a) (1 -Methyl-1 H-imidazol-4-yl)methanol A solution of 1 -methyl-1 H-imidazole-4-carboxylic acid (25 g, 198 mmol) in tetrahydrofuran (THF) (1000 ml_) was added LiAlhU (15.05 g, 396 mmol) slowly under nitrogen at room temperature. The reaction mixture was stirred at 50 °C for 12 h. It was added 15 mL of water, 15 mL of 10percent NaOH, 45 mL of water to the reaction mixture at 0 °C. The solid was filtered and the filtrate was concentrated to obtain the title compound (1 -methyl-1 H- imidazol-4-yl)methanol (13.2 g, 94 mmol, 47.5 percent yield) which was used for next step without further purification. LC-MS m/z 1 13.1 (M+H)+, 0.33 min (ret. time).

Reference: [1] Patent: WO2004/13134, 2004, A2, . Location in patent: Page 26
[2] Patent: WO2004/13135, 2004, A1, . Location in patent: Page 47
[3] Patent: WO2004/16606, 2004, A1, . Location in patent: Page 30
[4] Patent: WO2004/13138, 2004, A2, . Location in patent: Page 23
[5] Patent: WO2017/60854, 2017, A1, . Location in patent: Page/Page column 474; 475
  • 2
  • [ 127056-46-6 ]
  • [ 17289-25-7 ]
Reference: [1] Patent: US6255305, 2001, B1,
  • 3
  • [ 822-55-9 ]
  • [ 17289-25-7 ]
  • [ 38993-84-9 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 4950,4951, 4952
  • 4
  • [ 822-55-9 ]
  • [ 17289-25-7 ]
  • [ 38993-84-9 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 4950,4951, 4952
  • 5
  • [ 17289-25-7 ]
  • [ 17289-26-8 ]
YieldReaction ConditionsOperation in experiment
77% With manganese(IV) oxide In acetone at 60℃; for 12 h; Inert atmosphere 190b) 1 -Methyl-1 H-imidazole-4-carbal A solution of (1 -methyl-1 H-imidazol-4-yl)methanol (5 g, 44.6 mmol) in acetone (50 mL) was added manganese(IV) oxide (19.38 g, 223 mmol) slowly under nitrogen at room temperature. The reaction mixture was stirred at 60 °C for 12 h. The solid was filtered and the liquid was concentrated to obtain the title compound 1 -methyl-1 H-imidazole-4- carbaldehyde (4.12 g, 34.4 mmol, 77 percent yield) which was used in next step without further purification. LC-MS m/z 1 1 1 .2 (M+H)+, 0.49 min (ret. time).
Reference: [1] Patent: WO2017/60854, 2017, A1, . Location in patent: Page/Page column 475
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 19, p. 4728 - 4745
  • 6
  • [ 17289-25-7 ]
  • [ 17289-30-4 ]
YieldReaction ConditionsOperation in experiment
53.81% With thionyl chloride In dichloromethane at 0 - 20℃; Heating / reflux To a solution of intermediate 1 (5g, 44.64 [MMOL)] in CH2CI2 [(10 MI)] at [0°C] was added dropwise thionyl chloride (50 [ML)] and then the mixture was stirred at room temperature overnight and then under reflux for 3 hours and then concentrated under reduced pressure. The residue was treated with diethyl oxide and the resulting precipitate was filtered and dried. The title compound was obtained as a brown solid [(4G,] 53. 80percent); 1HNMR (300 MHz, [DS-DMSO, PPM). S] : 9.25 (s , 1H), 7.8 (s, 1H), 4.95 (s, 2H), 3.9 (s, 3H).
53.81% With thionyl chloride In dichloromethane at 20℃; for 3 h; To a solution of intermediate 22 (5g, 44.64 [MMOL)] in [CH2CI2] (10 ml) at [0°C] was added dropwise thionyl chloride (50 mi) and then the mixture was stirred at room temperature overnight and then at reflux for 3 hours. The mixture was concentrated under reduced pressure, and diethyl ether added. The resulting precipitate was filtered and dried to give the title product as a brown solid (4g, 53. [81percent) ;APOS;H] NMR (300 MHz, [D6-DMSO)] [] ppm: 9.25 (s, [1 H),] 7.8 (s, 1H), 4. 95 (s, 2H), 3.9 (s, 3H).
53.81% With thionyl chloride In dichloromethane at 0 - 20℃; Heating / reflux To a solution of intermediate 6 (5g, 44.64 [MMOL)] in CH2CI2 (10 ml) at [0°C] was added dropwise thionyl chloride (50 mi) and the mixture was stirred at room temperature overnight and then at reflux for 3 hours. The mixture was concentrated under reduced pressure and the residue taken up in diethyl ether to give a precipitate. The precipitate was filtered and dried to give the title compound [(4G,] 53. [81 percent) ;APOS;H] NMR (300 MHz, [DMSO-D6)] [6] ppm : 9.25 (s, [1 H),] 7.8 (s, [1 H),] 4.95 (s, 2H), 3.9 (s, [3H).]
Reference: [1] Patent: WO2004/13134, 2004, A2, . Location in patent: Page 26
[2] Patent: WO2004/13135, 2004, A1, . Location in patent: Page 47
[3] Patent: WO2004/13138, 2004, A2, . Location in patent: Page 23
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