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[ CAS No. 874-10-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 874-10-2
Chemical Structure| 874-10-2
Chemical Structure| 874-10-2
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Product Details of [ 874-10-2 ]

CAS No. :874-10-2 MDL No. :MFCD05663805
Formula : C8H8N2 Boiling Point : -
Linear Structure Formula :- InChI Key :BJZAXTJBEBNEDL-UHFFFAOYSA-N
M.W : 132.16 Pubchem ID :327957
Synonyms :

Calculated chemistry of [ 874-10-2 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.16
TPSA : 17.3 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) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 2.13
Log Po/w (WLOGP) : 1.64
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : 1.45
Consensus Log Po/w : 1.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.67
Solubility : 0.284 mg/ml ; 0.00215 mol/l
Class : Soluble
Log S (Ali) : -2.12
Solubility : 0.992 mg/ml ; 0.0075 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.44
Solubility : 0.483 mg/ml ; 0.00366 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.35

Safety of [ 874-10-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 874-10-2 ]

* 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 [ 874-10-2 ]
  • Downstream synthetic route of [ 874-10-2 ]

[ 874-10-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 1603-40-3 ]
  • [ 2032-35-1 ]
  • [ 874-10-2 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogen bromide In ethanol; water at 90℃; for 26 h; 2-amino-3-methylpyridine (10 g, 92.5 mmol) and 2-bromo-1,1-diethoxyethane (36.4 g, 185 mmol) were dissolved in ethanol (100 mL) Then, 48percent aqueous hydrogen bromide solution (9 mL) was slowly added dropwise to the reaction solution. After the reaction system was heated to 90 ° C for 26 hours, LC-MS detection reaction has ended, And then cooled to room temperature. The first reaction in the system of ethanol decompression distillation, The excess hydrobromic acid in the reaction was neutralized with excess saturated sodium bicarbonate water (100 mL) and sodium bicarbonate solids (15 g). The remaining mixture was extracted with ethyl acetate (200 mL x 3) All organic phases were then mixed and washed once with deionized water (100 mL) and saturated brine (100 mL) Dried over anhydrous sodium sulfate, Press the steam to remove the solvent. The remaining mixture was purified by silica gel column chromatography (eluent: dichloromethane / methanol = 0-10percent), To give 8-methyl-imidazo [1,2-a] pyridine (12 g, yield 98percent).
Reference: [1] Patent: CN106279160, 2017, A, . Location in patent: Paragraph 0259; 0263; 0264; 0265
[2] Bulletin of the Chemical Society of Japan, 1999, vol. 72, # 6, p. 1327 - 1334
  • 2
  • [ 107-20-0 ]
  • [ 1603-40-3 ]
  • [ 874-10-2 ]
YieldReaction ConditionsOperation in experiment
62% With sodium chloride; sodium hydrogencarbonate In water EXAMPLE IV
8-METHYLIMIDAZO[1,2-A]PYRIDINE
To a mixture of chloroacetaldehyde [25.4 mL (0.2 mole) of a 50percent aqueous solution]and 18.8 g (0.2 mole) of 2-amino-3-methylpyridine in 150 mL of water was added 16.8 g (0.2 mole) of sodium bicarbonate.
After being stirred at 25° C. for 3 days, the mixture was acidified with concentrated hydrochloric acid and stirred an additional 30 minutes.
After the pH was adjusted to 10 by addition of sodium hydroxide, the mixture was saturated with sodium chloride and extracted with ether.
The ether extracts were dried and concentrated to give 16.3 g (62percent) of a liquid residue, bp 68°-70° C. at 0.1 Torr.
Imidazo[1,2-a]pyridine, bp 61°-66° C. at 0.1 Torr., was prepared in an analogous manner.
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 23, p. 4415 - 4424
[2] Patent: US5039691, 1991, A,
[3] Patent: EP1790650, 2007, A1, . Location in patent: Page/Page column 45
  • 3
  • [ 637-81-0 ]
  • [ 136117-74-3 ]
  • [ 1033434-57-9 ]
  • [ 874-10-2 ]
YieldReaction ConditionsOperation in experiment
10%
Stage #1: at -30℃;
Stage #2: at -30 - 20℃;
Preparation of ethyl imidazopyridine propenoate (According to the Literature Method: Chezal, J. M. and al. J. Org. Chem. 2001, 66, 6576-6584).Ethyl azidoacetate (1.81 g, 14.0 mmol) was added dropwise at -30° C. to a stirred solution containing sodium (0.20 g, 8.70 mmol) in dry ethanol (10 mL). To this solution was added dropwise a solution of aldehyde 4 (1.00 mmol) in dry ethanol (8 mL). The reaction mixture was returned back room temperature and stirred for 3 h (CAUTION: an exothermic reaction can take place, with gas expansion). The solution was poured into aqueous saturated ammonium chloride solution (30 mL) and then extracted with CH2Cl2. The organic layers were dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by chromatography using CH2Cl2 as eluent to afford the azide derivative 6; Example 35
Ethyl α-azido-β-(imidazo[1,2-a]pyridin-8-yl)propenoate (6a)
From 4a (yield: 10percent); mp: 150-152° C.; IR (KBr) 2100, 1700, 1600, 1280 cm-1; 1H NMR (400 MHz, CDCl3) δ 1.41 (t, 3H, J=7 Hz), 4.39 (q, 2H, J=7 Hz), 6.83 (t, 1H, J=7 Hz), 7.57 (d, 1H, J=1 Hz), 7.61 (d, 1H, J=1 Hz), 7.76 (s, 1H), 8.06 (dd, 1H, J=7, 1 Hz), 8.17 (dd, 1H, J=7, 1 Hz). MS m/z 257 (M+, 1), 229 (61), 183 (100), 155 (31), 129 (23), 104 (14).
Further elution gave 8-methylimidazo[1,2-a]pyridine (yield: 10percent-Kaiser, C. and al. J. Med. Chem. 1992, 35, 4415-4424).
Reference: [1] Patent: US2010/93781, 2010, A1, . Location in patent: Page/Page column 22
  • 4
  • [ 1603-40-3 ]
  • [ 17157-48-1 ]
  • [ 874-10-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2856 - 2859
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