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[ CAS No. 29096-64-8 ] {[proInfo.proName]}

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Chemical Structure| 29096-64-8
Chemical Structure| 29096-64-8
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Product Details of [ 29096-64-8 ]

CAS No. :29096-64-8 MDL No. :MFCD13177175
Formula : C9H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :GVIYJQYRNBCBJR-UHFFFAOYSA-N
M.W : 160.17 Pubchem ID :15718182
Synonyms :

Calculated chemistry of [ 29096-64-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.39
TPSA : 34.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 1.78
Log Po/w (WLOGP) : 1.54
Log Po/w (MLOGP) : 0.4
Log Po/w (SILICOS-IT) : 1.24
Consensus Log Po/w : 1.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.577 mg/ml ; 0.0036 mol/l
Class : Soluble
Log S (Ali) : -2.12
Solubility : 1.21 mg/ml ; 0.00758 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.41
Solubility : 0.623 mg/ml ; 0.00389 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 29096-64-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 29096-64-8 ]

* 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 [ 29096-64-8 ]
  • Downstream synthetic route of [ 29096-64-8 ]

[ 29096-64-8 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 274-76-0 ]
  • [ 108-24-7 ]
  • [ 29096-64-8 ]
YieldReaction ConditionsOperation in experiment
22%
Stage #1: With aluminum (III) chloride In carbon disulfide at 0 - 20℃; Inert atmosphere
Stage #2: for 5.5 h; Reflux
To a solution of imidazo[1,2-a]pyridine (8.0 g, 67.7 mmol) in carbon disulfide (80 mL), was added powdered anhydrous AlCl3 (22.4 g, 169.4 mmol) carefully at 0° C. under inert atmosphere. After being stirred for 30 minutes at room temperature, the reaction mixture was refluxed gently and acetic anhydride (6.8 mL, 67.7 mmol) was added to the reaction mixture drop wise over a period of 30 minutes (at reflux temperature). The reaction mixture was continued at reflux temperature for 5 hours. Carbon disulfide was removed under vacuum. The residue was quenched with ice water (200 mL). The aqueous layer was extracted with DCM (2.x.200 mL). The organic extracts were washed with saturated NaHCO3 solution (2.x.100 mL), water (100 mL), and brine (100 mL). The organic layer was dried over anhydrous Na2SO4 and evaporated under vacuum to afford Int-1 (2.3 g, 22percent) as brown solid. 1H NMR (200 MHz, CDCl3): δ 9.67 (d, J=7 Hz, 1H), 8.36 (bs, 1H), 7.79 (d, J=8.8 Hz, 1H), 7.54-7.46 (m, 1H), 7.13-7.06 (m, 1H), 2.61 (s, 3H). Mass (m/z): 148 [M++1]. A solution of Int-1 (5 g, 31.2 mmol) in DMFDMA (25 mL) was stirred at reflux temperature for 36 hours under N2 atmosphere. After consumption of starting material as monitored by TLC, the reaction mixture was cooled to room temperature and diluted with ether (100 mL) and stirred for 15 minutes. The precipitated solid was filtered, washed with ether (2.x.10 mL) and dried under vacuum to provide Int-2 (4.7 g, 70percent) as brown solid. 1H NMR (200 MHz, CDCl3): δ 9.82 (d, J=6.8 Hz, 1H), 8.22 (s, 1H), 7.81 (d, J=12.2 Hz, 1H), 7.71 (d, J=8.8 Hz, 1H), 7.37 (t, J=7.4 Hz, 1H), 6.97 (t, J=6.2 Hz, 1H), 5.71 (d, J=12.2 Hz, 1H), 3.06 (bs, 6H). Mass (m/z): 216.0 [M++1]. To a solution of Int-2 (1.3 g, 6.0 mmol) in DMF (10 mL) was added Int-2B (3.5 g, 18.1 mmol) followed by K2CO3 (2.5 g, 18.1 mmol) at room temperature under inert atmosphere. Resulting mixture was heated at 100° C. for 16 hours. Reaction mixture was cooled to room temperature, poured into ice water (70 mL) and stirred for 15 minutes. The precipitated solid was filtered, washed with water (10 mL) and dried under vacuum to afford Int-3 (1.1 g, 55percent) as light brown solid. 1H NMR (200 MHz, dmso-d6): δ 10.11-10.05 (m, 2H), 8.64 (s, 1H), 8.52 (d, J=5.5 Hz, 1H), 7.85-7.63 (m, 5H), 7.46 (t, J=7.0 Hz, 1H), 7.32 (d, J=5.3 Hz, 1H), 7.07 (d, J=6.2 Hz, 1H), 3.75 (s, 3H). Mass (m/z): 345.9 [M++1]. To a solution of Int-3 (0.7 g, 2 mmol) in methanol (35 mL) and DCM (14 mL) was added hydroxylamine 50 wt percent solution in water (14 mL) at 0° C. After being stirred for 10 minutes at same temperature, NaOH solution (0.56 g in 3.5 mL of water) was added to reaction mixture at 0° C. The reaction mixture was allowed to warm up to room temperature and stirred for 5 hours. Volatiles were evaporated under vacuum, resulting residue was neutralized (about pH 7) using 2 N HCl at 0° C. and stirred for 10 min. The precipitated solid was filtered, washed with water (2.x.5 mL) and dried under vacuum. This crude material was purified by preparative high performance liquid chromatography (HPLC) (acetonitrile (ACN):Water:0.1percent trifluoroacetic acid (TFA)) to afford pure Compound 5 (0.22 g, 31percent) as its TFA salt as an off white solid. 1H NMR (200 MHz, dmso-d6): δ 11.05 (bs, 1H), 10.2 (d, J=6.6 Hz, 1H), 10.07 (s, 1H), 8.92 (bs, 1H), 8.59 (d, J=5.6 Hz, 1H), 7.96 (d, J=8.8 Hz, 1H), 7.86-7.72 (m, 5H), 7.52 (d, J=5.2 Hz, 1H), 7.39 (t, J=6.6 Hz, 1H). 13C NMR (120 MHz, dmso-d6): δ 164.4, 159.0, 158.5, 158.2, 158.0, 156.0, 142.7, 132.1, 131.0, 130.2, 127.6, 125.7, 121.7, 118.4, 115.9, 114.9, 108.2. Mass (m/z): 347.2 [M++1].
2.9 g
Stage #1: With aluminum (III) chloride In carbon disulfide at 20℃; for 0.5 h; Inert atmosphere
Stage #2: for 5 h; Reflux; Inert atmosphere
The imidazo [1,2-aM piperidine (59.3 mmoles) was dissolved in carbon disulfide (70 ml) under ice-cooling,Aluminum chloride (148.2 mmol) was added slowly, and repeatedly purged with nitrogen. At room temperature, after stirring for 30 minutes under reflux conditions Acetic anhydride (59.3 mmol) was slowly dropwise added to the system was added dropwise over 30 minutes period. The reaction in the reaction system under reflux for 5 hours, cooled. The solvent was removed by distillation under reduced pressure, the resulting residue was washed with a saturated aqueous sodium bicarbonate, washed with water and brine, dried over anhydrous sodium sulfate, and column chromatography (ethyl acetate: petroleum ether = 1: 8) afforded 2.9 g of the title compound. 12.9 g.
Reference: [1] Patent: US2010/29638, 2010, A1, . Location in patent: Page/Page column 65
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 9, p. 2245 - 2248
[3] Patent: EP1214318, 2003, B1, . Location in patent: Page/Page column 33
[4] Patent: EP1790650, 2007, A1, . Location in patent: Page/Page column 44
[5] Patent: CN103130792, 2016, B, . Location in patent: Paragraph 0223-0225
  • 2
  • [ 504-29-0 ]
  • [ 4637-24-5 ]
  • [ 598-31-2 ]
  • [ 29096-64-8 ]
YieldReaction ConditionsOperation in experiment
64%
Stage #1: for 23 h; Reflux
Stage #2: at 20℃; for 24 h;
2-Aminopyridine (1.88 g, 20 mmol) in 1,1-dimethoxyN,N-dimethylmethanamine (3.82 g, 32 mmol) was refluxed for 23 h and then evaporated. The resulting residue was dissolved in EtOH (35 mL), 1-bromoacetone (3.12 g, 22.75 mmol) was added and the reaction mixture was stirred at room temperature for 24 h. The reaction mixture was concentrated and the residue was purified by column chromatography (eluent: dichloromethane/methanol = 40:1) to afford 12s as a pale yellow solid (2.06 g, 64percent). Mp: 95-96 °C (Lit.Mp [20] 98-99 °C). 1H NMR (400 MHz, CDCl3): δ = 2.61 (s, 3H), 7.08 (t, J = 6.80 Hz, 1H), 7.50 (t, J = 8.00 Hz, 1H), 7.76 (d, J = 9.00 Hz, 1H), 8.34 (s, 1H), 9.65 (d, J = 6.84 Hz, 1H).
12%
Stage #1: at 90℃; for 3 h;
Stage #2: at 20℃; for 4 h;
A solution of intermediate 1 (20 g, 0.21 mol) and DMF-DMA (38 g, 0.32 mol) was stirred at 90° C. for 3 hrs. The mixture was concentrated in vacuum, the residue was dissolved in EtOH (200 ml), 1-bromopropan-2-one (32 g, 0.23 mol) was added dropwise, and the mixture was stirred at room temperature for 4 hrs. The solvent was concentrated in vacuum and purified by flash column chromatography to give intermediate 23 (4.1 g, 12percent) as a yellow solid. (0384) 1H NMR (CDCl3, 400 MHz): δ (ppm) 9.649.66 (m, 1H), 8.35 (s, 1H), 7.76 (d, 1H, J=8.8 Hz), 7.487.52 (m, 1H), 7.077.11 (m, 1H), 2.62 (s, 3H)
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 93, p. 381 - 391
[2] Patent: US2018/214458, 2018, A1, . Location in patent: Paragraph 0382-0395
  • 3
  • [ 504-29-0 ]
  • [ 77-76-9 ]
  • [ 598-31-2 ]
  • [ 29096-64-8 ]
YieldReaction ConditionsOperation in experiment
64%
Stage #1: for 23 h; Reflux
The 2-aminopyridine (1. 88g, 20mmol) wasdissolved in N,N-Dimethyl formamide Dimethyl Acetal(3.82g32mmol)and refluxed the reaction for 23h. The reaction solution was concentrated, intothe residue added 35mL ethanol and Bromoacetone(3. 12g, 22. 7mmol) andat room temperature keep the reaction for 24h. The reaction solution wasconcentrated and the residue was separated and purified with columnchromatography (Eluent, petroleum ether: ethyl acetate = 40: 1, v / v) toobtain pale yellow solid 2.06g, yield64percent.
Reference: [1] Patent: CN103508930, 2016, B, . Location in patent: Paragraph 0310-0313
  • 4
  • [ 504-29-0 ]
  • [ 598-31-2 ]
  • [ 29096-64-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 9, p. 2560 - 2565
  • 5
  • [ 34813-97-3 ]
  • [ 29096-64-8 ]
Reference: [1] Chemische Berichte, 1955, vol. 88, p. 1093,1100
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