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Chemical Structure| 133427-08-4 Chemical Structure| 133427-08-4

Structure of 133427-08-4

Chemical Structure| 133427-08-4

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CAS No.: 133427-08-4

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Product Details of [ 133427-08-4 ]

CAS No. :133427-08-4
Formula : C8H6N2O2
M.W : 162.15
SMILES Code : O=C(C1=CC=CN2C1=NC=C2)O
MDL No. :MFCD06739251
InChI Key :WHOCKNWCRFHEMH-UHFFFAOYSA-N
Pubchem ID :11715357

Safety of [ 133427-08-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280

Computational Chemistry of [ 133427-08-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 9
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 42.15
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

54.6 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.03
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.29
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.03
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.32
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.29
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.79

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.15
Solubility 1.16 mg/ml ; 0.00713 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.04
Solubility 1.49 mg/ml ; 0.0092 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.45
Solubility 5.77 mg/ml ; 0.0356 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.37 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.33

Application In Synthesis of [ 133427-08-4 ]

* 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.

  • Downstream synthetic route of [ 133427-08-4 ]

[ 133427-08-4 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 107-20-0 ]
  • [ 5345-47-1 ]
  • [ 133427-08-4 ]
YieldReaction ConditionsOperation in experiment
In ethanol; water; for 14h;Reflux; Example 9: Synthesis of 3-(4-Fluorophenyl)-imidazo[l,2-a]pyridine-8-carboxylic acid (9); Chloroacetaldehyde (45% aqueous solution) (6.6 mL, 38 mmol) is added to the stirred solution of 2-aminonicotinic acid (5.0 g, 25 mmol) in ethanol (35 mL) and warmed at reflux for 14 hours. The reaction mixture is concentrated and the crude material is triturated with EtOH-Et20 to afford imidazo[l,2-a]pyridine-8-carboxylic acid. Mp: 296-299C.
  • 2
  • [ 133427-08-4 ]
  • [ 530-62-1 ]
  • imidazo[1,2-<i>a</i>]pyridin-8-yl-imidazol-1-yl-methanone [ No CAS ]
  • 3
  • [ 133427-08-4 ]
  • Imidazo[1,2-a]pyridine-8-carboxylic acid [(1S,7aS)-1-(hexahydro-pyrrolizin-1-yl)methyl]-amide [ No CAS ]
  • 4
  • [ 133427-07-3 ]
  • [ 133427-08-4 ]
YieldReaction ConditionsOperation in experiment
The solution was concentrated under reduced pressure to remove the methanol, the aqueous solution acidified using 2N hydrochloric acid, and the mixture evaporated under reduced pressure to give the title compound as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz) delta: 7.60 (dd, 1H), 8.10 (s, 1H), 8.41 (d, 1H), 8.55 (s, 1H), 9.18 (d, 1H) LRMS: m/z ES+ 163 [MH]+
[0310] Lithium hydroxide solution (2.5 mL, 1M in water) was added to a solution of the ester from preparation 8 (400 mg, 2.27 mmol) in methanol (5 mL) and the solution stirred at room temperature for 90 minutes. The solution was concentrated in vacuo to remove the methanol, the aqueous solution acidified using 2M hydrochloric acid, and the mixture concentrated in vacuo to give the title compound as a yellow solid. [0311] 1HNMR (DMSO-D6, 400 MHz): 7.60 (dd, 1H), 8.10 (s, 1H), 8.41 (d, 1H), 8.55 (s, 1H), 9.18 (d, 1H) [0312] MS TSP+ m/z 163 [MH]+
[0306] [C00009] [00009] [0307] Lithium hydroxide solution (2.5 ml, 1M in water) was added to a solution of the ester from preparation 3 (400 mg, 2.27 mmol) in methanol (5 ml) and the solution stirred at room temperature for 90 minutes. The solution was concentrated in vacuo to remove the methanol, the aqueous solution acidified using 2M hydrochloric acid, and the mixture evaporated under reduced pressure to give the title compound as a yellow solid. [0308] 1H NMR (DMSO-D6, 400 MHz): delta: 7.60 (dd, 1H), 8.10 (s, 1H), 8.41 (d, 1H), 8.55 (s, 1H), 9.18 (d, 1H) [0309] MS TSP+m/z 163 [MH]+
  • 5
  • [ 830347-59-6 ]
  • [ 133427-08-4 ]
  • syn-imidazo[1,2-a]pyridine-8-carboxylic acid (4-[2-(2,3-dihydro-benzo[b]thiophen-6-yloxy)-5-fluoro-pyridine-3-carbonyl]-amino}-cyclohexyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% EXAMPLE 1 Syn-Imidazo[1,2-a]Pyridine-8-Carboxylic Acid (4-[2-(2,3-Dihydro-Benzo[b]Thiophen-6-Yloxy)-5-Fluoro-Pyridine-3-Carbonyl]-Amino}-Cyclohexyl)-Amide The amine of preparation 7 (150 mg, 0.39 mmol), the carboxylic acid of preparation 4 (87 mg, 0.43 mmol), 1-hydroxybenzotriazole hydrate (58 mg, 0.43 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (82 mg, 0.43 mmol) and 4-methylmorpholine (47 muL, 0.43 mmol) were dissolved in dichloromethane (20 mL) and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue dissolved in N,N-dimethylformamide (10 mL) and stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo, the residue partitioned between ethyl acetate (50 mL) and water (30 mL) and the organic layer washed with brine, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluding with pentane:ethyl acetate 85:15 to 0:100. The crude product was purified by column chromatography on silica gel again, eluding with ethyl acetate to yield the title product as a white solid, 130 mg (63%). 1H NMR(CDCl3, 400 MHz): delta: 1.90(m, 8H), 3.30(t, 2H), 3.40(t, 2H), 4.20(m, 1H), 4.30(m, 1H), 6.85(m, 1H), 7.00(t, 1H), 7.05(s, 1H), 7.20(d, 1H), 7.45(s, 1H), 7.65(s, 1H), 8.05(m, 2H), 8.25(m, 2H), 8.35(m, 1H), 10.50(m, 1H) MS ES+m/z 554 [MNa]+ Microanalysis: Observed-C=61.99%, H=4.90%, N=12.86% C28H26FN5O3S Calculated-C=62.00%, H=5.05%, N=12.91%
  • 6
  • syn-N-(4-amino-cyclohexyl)-5-fluoro-2-(3-methylsulphanyl-phenoxy)-nicotinamide hydrochloride [ No CAS ]
  • [ 133427-08-4 ]
  • syn-imidazo[1,2-a]pyridine-8-carboxylic acid (4-[5-fluoro-2-(3-methylsulfanyl-phenoxy)-pyridine-3-carbonyl]-amino}-cyclohexyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20℃; for 18h; EXAMPLE 6 Syn-<strong>[133427-08-4]Imidazo[1,2-a]pyridine-8-carboxylic acid</strong>(4-[5-fluoro-2-(3-methylsulfanyl-phenoxy)-pyridine-3-carbonyl]-amino}-cyclohexyl)-amide The amine of preparation 18 (250 mg, 0.60 mmol) was dissolved in N,N-dimethylformamide (7 mL) and the solution treated with 1-hydroxybenzotriazole hydrate (84 mg, 0.60 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (124 mg, 0.69 mmol), 4-methylmorpholine (205 muL, 1.88 mmol) and the carboxylic acid of preparation 9 (90 mg, 0.55 mmol). The reaction mixture was stirred at room temperature for 18 hours. The mixture was diluted with ethyl acetate:water 3:1 (28 mL) and the aqueous extracted with ethyl acetate (*2). The organics were washed with 10% citric acid solution (7 mL), saturated sodium hydrogen carbonate solution (7 mL) and brine (7 mL). The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluding with pentane:ethyl acetate 70:30 to 20:80 to yield the title product, 80 mg. 1H-NMR(CDCl3, 400 MHz): 1.91(m, 8H), 2.43(s, 3H), 4.23(m, 1H), 4.32(m, 1H), 6.94(m, 2H), 7.06(m, 1H), 7.14(m, 1H), 7.31(m, 1H), 7.37(m, 1H), 7.60(m, 1H), 8.01(m, 1H), 8.06(m, 1H), 8.17(s, 1H), 8.24(d, 1H), 8.36(m, 1H), 10.53(m, 1H). MS ES+ m/z 520 [MH]+
  • 7
  • [ 5345-47-1 ]
  • [ 2032-35-1 ]
  • [ 133427-08-4 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 150℃; for 2h;microwave irradiation;Product distribution / selectivity; Step A: Preparation of Imidazo[l,2-alpha]pyridine-8-carboxylic Acid.2-Aminonicotinic acid (2.0 g, 14.48 mmol) and 2-bromo-l,l-diethoxyethane (2.247 mL, 14.48 mmol) in acetonitrile (10 mL) were heated at 150 0C for 2 h under microwave irradiation. The resulting precipitate was filtered off and washed with acetonitrile and hexane to afford the title compound (2.783 g) as a solid. Exact mass calculated for C8H6N2O2: 162.0. Found: LCMS mlz = 163.1 (M + H)+. 1H NMR (400 MHz, Methanol-^) delta 7.62 (dd, J = 6.82, 7.33 Hz, IH), 8.06 (d, J = 2.27 Hz, IH), 8.36 (d, J = 2.02 Hz, IH), 8.62 (d, J = 7.33 Hz, IH), 9.04 (d, J = 6.82 Hz, IH). Step B: Preparation of 3-Bromoimidazo[l,2-alpha]pyridine-8-carboxylic Acid.Imidazo[l,2-alpha]pyridine-8-carboxylic acid (100 mg, 617 mumol), l-bromopyrrolidine-2,5- dione (110 mg, 617 mumol) and N,N-dimethylformamide (1.5 mL) were stirred at room temperature for 1 h. The resulting precipitate was filtered off and washed with acetonitrile and hexane to afford the title compound as a solid (68 mg).
  • 8
  • [ 5345-47-1 ]
  • [ 7252-83-7 ]
  • [ 133427-08-4 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 150℃; for 2h;microwave irradiation;Product distribution / selectivity; Example 1.3: Preparation of (4-(2,4-Difluorophenethyl)piperazin-l-yl)(imidazo[l,2- alpha]pyridin-8-yl)methanone (Compound 3).Step A: Preparation of Imidazo[l,2-alpha]pyridine-8-carboxylic Acid.To a mixture of 2-aminonicotinic acid (0.6906 g, 5.00 mmol) in acetonitrile (20 mL) was added bromoacetaldehyde dimethyl acetal (0.591 mL, 5.00 mmol). The resulting slurry was heated at 150 0C under microwave irradiation for 2 h. The resulting precipitate was filtered off and washed with acetonitrile and hexane to afford the title compound (0.924 g) as a grey solid.
0.924 g In acetonitrile; at 150℃; for 2h;Microwave irradiation; To a mixture of 2-aminonicotinic acid (0.69 g, 5.00 mmol) in CH3CN (20 mL) was added bromoacetaldehyde dimethyl acetal (0.59 mL, 5.00 mmol). The resulting slurry was heated to 150 C under microwave irradiation for 2 h. The resulting precipitate was filtered off and washed with CH3CN and hexane to afford H-imidazo[1,2-alpha]pyridine-8-carboxylic acid (0.924 g) as a grey solid.
  • 9
  • [ 133427-08-4 ]
  • [ 1116691-26-9 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 1h; Step B: Preparation of 3-Bromoimidazo[l,2-alpha]pyridine-8-carboxylic Acid.Imidazo[l,2-alpha]pyridine-8-carboxylic acid (100 mg, 617 mumol), l-bromopyrrolidine-2,5- dione (110 mg, 617 mumol) and N,N-dimethylformamide (1.5 mL) were stirred at room temperature for 1 h. The resulting precipitate was filtered off and washed with acetonitrile and hexane to afford the title compound as a solid (68 mg).
  • 10
  • [ 1116691-47-4 ]
  • [ 133427-08-4 ]
  • [ 1116690-51-7 ]
YieldReaction ConditionsOperation in experiment
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In ethyl acetate; N,N-dimethyl-formamide; for 2h;Product distribution / selectivity; Step E: Preparation of (4-(2,4-Difluorophenethyl)piperazin-l-yl)(imidazo[l,2- alpha]pyridin-8-yl)methanone (Compound 3).To a solution of imidazo[l,2-alpha]pyridine-8-carboxylic acid (36.6 mg, 226 mumol), l-(2,4- difluorophenethyl)piperazine hydrochloride (45.0 mg, 150 mumol) and triethylamine (210 mul, 1504 mumol) in DMF (0.75 mL) was added 1-propylphosphonic acid anhydride solution (50% in ethyl acetate, 183 muL, 0.301 mmol). The mixture was stirred for 2 h, quenched with water and purified by preparative HPLC/MS. The resultant lyophilate was dissolved in DCM, treated with <n="55"/>MP-carbonate resin (-200 mg). The mixture was stirred for 30 min and filtered to remove the resin. The solvent was removed under reduced pressure to afford the title compound as a white solid (33.0 mg).
  • 11
  • [ 133427-08-4 ]
  • [ 885276-95-9 ]
  • 12
  • [ 133427-08-4 ]
  • [ 1300022-42-7 ]
  • 13
  • [ 67-56-1 ]
  • [ 133427-08-4 ]
  • [ 133427-07-3 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; for 8h;Reflux; To a stirred solution of imidazo[l,2-a]pyridine-8-carboxylic acid (3.8 g, 23 mmol) in methanol (100 mL) is added thionylchloride (8.36 g, 70.3 mmol) and the mixture is warmed at reflux. After 8 hours, the reaction mixture is cooled to room temperature and quenched with saturated aqueous NaHCC>3, and extracted with EtOAc (3 x 250 mL). The combined organic layers are washed with water, brine, dried over Na2S04 and concentrated. The crude material is purified by silica gel chromatography eluting with 3% MeOH in CH2CI2 to afford imidazo[l,2-a]pyridine-8-carboxylic acid methyl ester. Mp: 71-73C.
  • 14
  • 1-(2,4-difluorophenethyl)piperazine dihydrochloride [ No CAS ]
  • [ 133427-08-4 ]
  • [ 121-44-8 ]
  • [ 1116690-51-7 ]
YieldReaction ConditionsOperation in experiment
33 mg With propylphosphonic acid; In ethyl acetate; N,N-dimethyl-formamide; for 2h; To a solution of H-imidazo[1,2-alpha]pyridine-8-carboxylic acid (36.6 mg, 226 mumol), 1-(2,4-difluorophenethyl)piperazine dihydrochloride (45.0 mg, 150 mumol), and triethylamine (210 mul, 1504 mumol) in DMF (0.75 mL) was added 1-propylphosphonic acid anhydride solution (50 wt % in ethyl acetate, 183 muL, 0.301 mmol). The mixture was stirred for 2 h, quenched with water and purified by HPLC to give 35 (33.0 mg) as a white solid.
  • 15
  • [ 133427-08-4 ]
  • [(7S)-2,7-Dimethyl-3-(3,4,5-trifluorophenyl)-5,7-dihydro-4H-pyrazolo[3,4-c]pyridin-6-yl]-imidazo[1,2-a]pyridin-8-yl-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 392 [(7S)-2,7-Dimethyl-3-(3,4,5-trifluorophenyl)-5,7-dihydro-4H-pyrazolo[3,4-c]pyridin-6-yl]-imidazo[1,2-a]pyridin-8-yl-methanone The title compound was prepared in a manner analogous to Example 288, using <strong>[133427-08-4]imidazo[1,2-a]pyridine-8-carboxylic acid</strong> instead of 2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid. MS (ESI): mass calcd. for C22H18F3N5O, 425.2; m/z found, 426.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 8.69-8.56 (m, 1H), 8.08-7.98 (m, 1H), 7.63-7.46 (m, 3H), 7.28-7.18 (m, 1H), 6.96 (t, J=6.8 Hz, 1H), 5.66 (q, J=6.7 Hz, 1H), 4.85-4.55 (m, 1H), 3.86-3.69 (m, 3H), 3.25-3.00 (m, 1H), 2.83-2.63 (m, 1H), 2.33-2.14 (m, 1H), 1.42 (dd, J=68.2, 6.8 Hz, 3H).
 

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