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Chemical Structure| 552850-73-4 Chemical Structure| 552850-73-4

Structure of 552850-73-4

Chemical Structure| 552850-73-4

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Product Details of [ 552850-73-4 ]

CAS No. :552850-73-4
Formula : C7H5ClN2O3
M.W : 200.58
SMILES Code : O=C(O)C(NC1=NC=C(Cl)C=C1)=O
MDL No. :MFCD12171750
InChI Key :UQMUSEDZBHNTTQ-UHFFFAOYSA-N
Pubchem ID :23087882

Safety of [ 552850-73-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H319-H372-H410
Precautionary Statements:P260-P264-P273-P301+P312-P305+P351+P338-P314
Class:9
UN#:3077
Packing Group:

Computational Chemistry of [ 552850-73-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 45.33
TPSA ?

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

79.29 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.49
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

0.95
Log Po/w (WLOGP)?

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

0.57
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.

-0.43
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

0.49
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.41

Water Solubility

Log S (ESOL):?

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

-1.83
Solubility 3.0 mg/ml ; 0.0149 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-2.2
Solubility 1.26 mg/ml ; 0.00628 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

-2.02
Solubility 1.92 mg/ml ; 0.00955 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

No
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

No
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.

-6.85 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

0.0
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

1.0 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)

1.76

Application In Synthesis of [ 552850-73-4 ]

* 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 [ 552850-73-4 ]

[ 552850-73-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 480450-68-8 ]
  • [ 552850-73-4 ]
YieldReaction ConditionsOperation in experiment
Method D: Twenty one mM acid chloride were dissolved in 10 ml tetrahydrofuran and added to a mixture of 20 mM 2-amino-5-chloropyridine, 3.5 ml (25 mM) triethylamine and 40 ml tetrahydrofuran as described in method C. The mixture was stirred for 15 min prior to filtration to remove the triethylamine hydrochloride. The solid was washed with 10 ml tetrahydrofuran and the combined filtrates evaporated under reduced pressure. In case of the oxalyl derivate, the residue was dissolved in 90 ml hot 95% ethanol and the solution filtered while still hot. The mixture was stirred and 40 mM KOH dissolved in 10 ml water were added at a rate that the temperature did not rise above 40C. The reaction was completed by stirring for a further 10 min. The product separated as white potassium salt which was collected by suction. The precipitate was dissolved in 100 ml (iodo derivative: 250 ml) hot water and filtrated. Hydrochloric acid was added to the hot filtrate until pH2. The product separated as free acid during incubation at 4C overnight. The product was further purified by recrystallisation from 95% ethanol. In case of the malonyl and adipoyl derivatives, the residue was dissolved in 200 ml MeOH and filtrated. The solution was placed in a triple-necked round bottom flask equipped with a reflux condenser, a dropping funnel and a thermometer and heated to 50C. While stirring the mixture, 40 mM KOH dissolved in 40 ml water were rapidly added through the dropping funnel and the temperature maintained at 50C. The reaction was completed by stirring at the same temperature for an additional 10 min. The surplus of KOH was neutralised by addition of 40 mM NH4Cl dissolved in 10 ml water. Most solvent was removed under reduced pressure and the residue dissolved in water (about 200 ml) and filtered. Formic acid was added to the clear filtrate until pH3. The product separated as white crystals during incubation at 4C overnight. The malonyl and adipoyl derivatives were purified by recrystallisation from 95% or 50% ethanol, respectively.
With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 20℃; for 3h; To a solution of methyl 2-((5-chloropyridin-2-yl)amino)-2-oxoacetate (Int 10/3) (0.50 g, 2.30 mmol) in THF (8 mL), MeOH (5 mL) and H20 (5 mL) was added LiOH H20 (289 mg, 6.90 mmol). The mixture was stirred at rt for 3 h. It was concentrated and the residue was diluted with H2O (10 mL). It was acidified with 1 N HCI solution to pH = 6-7 and extracted with EtOAc (3 x 30 mL). The combined organic layers were washed with brine (30 mL), dried over Na2S04, filtered and concentrated to give the title compound as a yellow solid.
  • 2
  • [ 552850-73-4 ]
  • (3S,3aS)-3-aminomethyl-7-(3-oxomorpholin-4-yl)-3a,4-dihydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-1(3H)-one [ No CAS ]
  • N1-(5-chloropyridin-2-yl)-N2-(((3S,3aS)-1-oxo-7-(3-oxomorpholino)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)oxalamide [ No CAS ]
  • 3
  • tert-butyl {(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl}carbamate monooxalate [ No CAS ]
  • [ 552850-73-4 ]
  • [ 480452-36-6 ]
YieldReaction ConditionsOperation in experiment
91.05% With dibutyltin(II) dilaurate; sodium hydrogencarbonate; at 50 - 70℃; for 5h;pH 7.0;Autoclave; Industrial scale; 1863.8 gTert-butyl {(1R, 2S, 5S) -2-amino-5 - [(dimethylamino) carbonyl] cyclohexyl} carbamate oxalate monohydrate (7.03 mol) was added to 50 LIn the reaction kettle,Then 20 LC2 fatty alcohol was added,Adding a saturated solution of sodium hydrogencarbonate to adjust PH = 7,After addition, 2146.7 g of 2- [(5-chloropyridin-2-yl) amino] -2-oxoacetic acid (5.86 mol)The reaction solution was then heated to 50 C, dibutyltin dilaurate was added,After the addition, the reaction solution was heated to 70 C and kept stirred for 5 h. The reaction was monitored by TLC until the starting point disappeared.The reaction solution was poured into ice water, filtered, and the filter cake was washed with water,To obtain 2496.92 g of dry white powder 91.05%.
  • 4
  • [ 552850-73-4 ]
  • 4-[4-(3-aminooxetan-3-yl)phenyl]morpholin-3-one [ No CAS ]
  • N'-(5-chloropyridin-2-yl)-N-{3-[4-(3-oxomorpholin-4- yl)phenyl]oxetan-3-yl}oxalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
6% To a solution of 2 - ((5- chloropyridin-2-yl) amino) -2-oxoacetic acid (48 mg, 0.239 mmol)In N, N-dimethylformamide (1 mL)Triethylamine (100 [mu] L, 0.72 mmol)And HBTU (114 mg, 0.3 mmol),Stir for 10 minutes,4- (4- (3-Amino-3-yl) phenyl) morpholin-3- one (160 mg, 0.644 mmol)Stir at room temperature for 4 hours.The crude product was purified by column chromatography (dichloromethane / methanol (v / v) = 10/1)A pale yellow oil (6.2 mg, 6%) was obtained.
  • 5
  • [ 332398-35-3 ]
  • [ 552850-73-4 ]
  • methyl 4-(1-(2-((5-chloropyridin-2-yl)amino)-2-oxoacetyl)piperidin-4-yl)-1-naphthoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h; To a stirred solution of <strong>[552850-73-4]2-((5-chloropyridin-2-yl)amino)-2-oxoacetic acid</strong> (Int 13) (160 mg, 0.80 mmol), HOBt (108 mg, 0.80 mmol), DIPEA (620 mg, 4.80 mmol), and EDCI (305 mg, 1.60 mmol) in DMF (6 ml_) was added methyl 4-(piperidin-4-yl)-1 -naphthoate (Int 20/12) (269 mg, 0.88 mmol) at rt. The mixture was stirred at rt for 16 h, diluted with H2O (20 mL) and extracted with EtOAc (3 x 20 ml_). The combined organic layers were washed with brine (30 mL), dried over Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography, eluting with PE: EtOAc = 1 :1 (v/v) to give the title compound as a white solid.
  • 6
  • [ 552850-73-4 ]
  • 4-(1-(2-((5-chloropyridin-2-yl)amino)-2-oxoacetyl)piperidin-4-yl)-1-naphthoic acid [ No CAS ]
 

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[ 552850-73-4 ]

Chemical Structure| 480450-83-7

A1448926 [480450-83-7]

Lithium 2-((5-chloropyridin-2-yl)amino)-2-oxoacetate

Reason: Free-salt