171178-47-5|6-Chloropyrido[3,4-d]pyrimidin-4(3H)-one| Ambeed

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Quality Control of [ 171178-47-5 ] Purity: 97% SDS Specification

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Product Details of [ 171178-47-5 ]

CAS No. :	171178-47-5
Formula :	C₇H₄ClN₃O
M.W :	181.58
SMILES Code :	ClC2=CC1=C(N=CNC1=O)C=N2
MDL No. :	MFCD11044635
InChI Key :	BBPUOYYUBFLNML-UHFFFAOYSA-N
Pubchem ID :	135480525

Safety of [ 171178-47-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 171178-47-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	45.17
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	58.64 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.05
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.6
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.97
Log P_o/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.	0.54
Log P_o/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	2.23
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.08

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.96
Solubility	1.99 mg/ml ; 0.011 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.	-1.41
Solubility	7.14 mg/ml ; 0.0393 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-3.48
Solubility	0.0604 mg/ml ; 0.000333 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.	-6.98 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.	0.55

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)	1.72

Application In Synthesis of [ 171178-47-5 ]

* 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 [ 171178-47-5 ]

[ 171178-47-5 ] Synthesis Path-Downstream 1~35

1
[ 171178-47-5 ]
[ 171178-48-6 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; N,N-dimethyl-formamide; for 16h;Reflux;	a) Method for synthesising P-1 a:; delta-amino^-chloro-isonicotinic acid (4 g, 23.18 mmol) is taken up in the form of the amide (50 ml.) and stirred for 12 h at 140 0C. The reaction mixture is cooled to RT and mixed with water. The precipitate formed is filtered off, washed with water and then dried at 60 0C for 24h in the vacuum drying cupboard.The intermediate product obtained, 6-chloro-3/-/-pyrido[3,4-c/]pyrimidin-4-one (745 mg, 4.1 mmol), is suspended in thionyl chloride (10 ml_), mixed with one drop of DMF and refluxed for 16 h. The excess thionyl chloride is distilled off. The residue is taken up in DCM, washed 1x with semisaturated NaHCC>;3 solution and saturated NaCI solution, dried on Na2SC>;4 and concentrated to dryness by rotary evaporation. The crude product P-1a is further used directly.
	With thionyl chloride; N,N-dimethyl-formamide; for 2h;Reflux;	Step 2: containing 20 ml sulfoxide chloride, 1.81 g of 6-chloro-pyrrolo [3,4-d] pyrimidin -4 (3H) - one (10 mmol) and dimethylformamide (catalytic amount ) was heated to reflux for 2 hours, the solvent evaporated the crude product was directly used in the next step without any further purification.

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1401 - 1405.
[2]Journal of Medicinal Chemistry,1996,vol. 39,p. 1823 - 1835.
[3]Patent: WO2010/94695,2010,A1 .Location in patent: Page/Page column 35.
[4]Journal of Medicinal Chemistry,2014,vol. 57,p. 3484 - 3493.
[5]Patent: TWI525093,2016,B .Location in patent: Page/Page column 93.

2
[ 77287-34-4 ]
[ 58483-95-7 ]
[ 171178-47-5 ]

Yield	Reaction Conditions	Operation in experiment
83.9%	at 140℃;Product distribution / selectivity;	Step (e): 6-CHLORO-3H-PYRIDO [3, 4-D] PYRIMIDIN-4-ONE A suspension of 5-amino-2-chloro-isonicotinic acid in formamide (240 mL) was heated at an internal temperature of 140°C overnight with stirring. The mixture was cooled to room temperature, diluted with water (600mL), and stirred for 1 hour. The resulting solid was collected by filtration, washed with water, and dried to give 17. 20g of 6-chloro-3H-pyrido [3, 4-d] PYRIMIDIN-4-ONE as a brown solid (83. 9percent yield). 1H NMR (400 MHz, DMSO-D6) d ppm 7.9 (s, 1H), 8.2 (s, 1H), 8.9 (s, 1H), 12.7 (bs, 1H) MS (APCI) M+1 = 182.0
	at 140℃; for 12h;	a) Method for synthesising P-1 a:; delta-amino^-chloro-isonicotinic acid (4 g, 23.18 mmol) is taken up in the form of the amide (50 ml.) and stirred for 12 h at 140 0C. The reaction mixture is cooled to RT and mixed with water. The precipitate formed is filtered off, washed with water and then dried at 60 0C for 24h in the vacuum drying cupboard.The intermediate product obtained, 6-chloro-3/-/-pyrido[3,4-c/]pyrimidin-4-one (745 mg, 4.1 mmol), is suspended in thionyl chloride (10 ml_), mixed with one drop of DMF and refluxed for 16 h. The excess thionyl chloride is distilled off. The residue is taken up in DCM, washed 1x with semisaturated NaHCC>;3 solution and saturated NaCI solution, dried on Na2SC>;4 and concentrated to dryness by rotary evaporation. The crude product P-1a is further used directly.

References: [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 2221 - 2226.
[2]Patent: WO2005/16926,2005,A1 .Location in patent: Page/Page column 116.
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 3484 - 3493.
[4]Patent: WO2010/94695,2010,A1 .Location in patent: Page/Page column 35.

3
[ 3473-63-0 ]
[ 58483-95-7 ]
[ 171178-47-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	In 2-methoxy-ethanol; for 18h;Heating / reflux;Product distribution / selectivity;	Step (e) 6-Chloro-3H-pyrido [3,4-d] pyrimidin-4-one A 1 L round bottomed flask was charged with 5-amino-2-chloro- isonicotinic acid (69.5 g, 0.40 moles), formamidine acetate (84 g, 0.81 moles, 2 mole equivalents), and 600 mL of methoxyethanol. The resulting solution was heated at reflux for 18 hours. After cooling to 5°C, a precipitate was collected by filtration, washed twice with methoxyethanol, and dried overnight in the vacuum oven at 45°C. The reaction yielded 67 g (92percent total yield) of 6-chloro-3H- pyrido [3, 4-D] PYRIMIDIN-4-ONE as a tan solid that was sufficiently pure by NMR to use in the next reaction. 8H (DMSO) 12.70 (1 H, s), 8.86 (1 H, d), 8. 19 (1 H, s), 7.93 (1 H, d) MS [M+H3+ 182

References: [1]Patent: WO2005/16926,2005,A1 .Location in patent: Page/Page column 123-124.
[2]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1401 - 1405.

4
[ 124-40-3 ]
[ 171178-47-5 ]
[ 189680-98-6 ]