629655-23-8|2-Chloro-3-nitropyridin-4-ol| Ambeed

Structure of 2-Chloro-3-nitropyridin-4-ol
CAS No.: 629655-23-8

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Quality Control of [ 629655-23-8 ] Purity: 98% SDS Specification

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Product Details of [ 629655-23-8 ]

CAS No. :	629655-23-8
Formula :	C₅H₃ClN₂O₃
M.W :	174.54
SMILES Code :	OC1=C([N+]([O-])=O)C(Cl)=NC=C1
MDL No. :	MFCD07778466
InChI Key :	RGJVVCCIZKLJRL-UHFFFAOYSA-N
Pubchem ID :	45789635

Safety of [ 629655-23-8 ]

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

Computational Chemistry of [ 629655-23-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	40.09
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	78.94 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.98
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	1.84
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.35
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.	-0.7
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	-0.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.59

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.42
Solubility	0.665 mg/ml ; 0.00381 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.	-3.12
Solubility	0.133 mg/ml ; 0.000762 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	-1.44
Solubility	6.29 mg/ml ; 0.0361 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.	-6.06 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	3.0 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)	2.01

Application In Synthesis of [ 629655-23-8 ]

* 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.

Downstream synthetic route of [ 629655-23-8 ]

[ 629655-23-8 ] Synthesis Path-Downstream 1~35

1
[ 24358-62-1 ]
[ 629655-23-8 ]
2-[(R)-1-(4-Bromo-phenyl)-ethylamino]-3-nitro-pyridin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In butan-1-ol; at 110℃; for 48h;	A solution of <strong>[629655-23-8]2-chloro-3-nitro-4-hydroxypyridine</strong> (4.99 g, 28.59 mmol) and (1R)-1-(4-bromophenyl)ethanamine (5.20 g, 25.99 mmol) and 3.61 mL (25.99 mmol) of triethylamine (TEA) in 50 mL of n-butanol was heated to 110 C. for 48 hours. The solvent was removed in vacuo and the crude mixture filtered through silica gel using CH2Cl2. The solvent was removed in vacuo and the crude material (4.2 g) diluted with 50 mL of acetonitrile, treated with 4 mL of phosphorous oxychloride (POCl3), and the reaction mixture was heated to 80 C. for three hours. Additional POCl3 was added during this time to drive the reaction to completion. The solvent was concentrated in vacuo, diluted with EtOAc, washed with aqueous sodium bicarbonate and brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was subjected to silica gel chromatography eluted with 10-30% ethyl acetate in hexanes to afford N-[(1R)-1-(4-bromophenyl)ethyl]-4-chloro-3-nitropyridin-2-amine with a mass ion (ES+) of 338.0 for M+H+(Br79).

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6439 - 6442.
[2]Patent: US2004/29920,2004,A1 .Location in patent: Page/Page column 15.

2
[ 5975-12-2 ]
[ 629655-23-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium acetate; In N,N-dimethyl-formamide; at 120℃; for 5h;	To a solution of 2 , 4-dichloro-3-nitropyridine (100 g, 518 mmol) in N,iV-dimethylformamide (500 mL) was added sodium acetate (106 g, 1295 mmol) at room temperature. The mixture was stirred at 120C for 5 hours. The reaction completion was confirmed by TLC, then the mixture was cooled to room temperature and diluted with water (500 mL) followed by aqueous 2N HC1 solution to adjust the pH < 4. The aqueous layer was extracted with ethyl acetate (5 x 750 mL) . The combined organic layers were washed with brine, dried over sodium sulfate and under vacuum to give a crude product. The crude product was triturated with water, and the resulting solid was collected by filtration, and dried under vacuum to give the title compound (63 g, 65%). MS(ESI)m/z: 175.1 (M+l); XH NMR (400 MHz, DMSO-d6) : delta 7.10 (d, J = 6.0 Hz, 1H) , 8.25 (d, J = 5.6 Hz, 1H) , 13.10 (br s, 1H) .
60%	With sodium acetate; In N,N-dimethyl-formamide; at 120℃; for 3h;	[0715] To a solution of XIV-2 (10 g, 52.1 mmol) in DMF (60 mL) was added NaOAc (10.3 g, 125 mmol), the reaction mixture was stirred at 120 C. for 3 hrs. The mixture was cooled to rt and poured into water, extracted with EtOAc. Combined organic phase was washed with brine and concentrated under vacuum to afford the crude product. The residue was purified by column chromatography (PE:EA=1:1) to afford XIV-3 as a pale yellow solid (5.4 g, 60% yield). 1HNMR (CD3OD, 300 MHz) delta 8.14 (d, J=6.0 Hz, 1H), 6.98 (d, J=6.0 Hz, 1H).
60%	With sodium acetate; In N,N-dimethyl-formamide; at 120℃; for 3h;	To a solution of XIV-2 (10 g, 52.1 mmol) in DMF (60 mL) was added NaOAc (10.3 g, 125 mmol), the reaction mixture was stirred at 120C for 3 hrs. The mixture was cooled to rt and poured into water, extracted with EtOAc. Combined organic phase was washed with brine and concentrated under vacuum to afford the crude product. The residue was purified by column chromatography (PE:EA=1:1) to afford XIV-3 as a pale yellow solid (5.4 g, 60% yield). ?HNMR (CD3OD, 300MHz) oe 8.14 (d, J=6.0 Hz, 1H), 6.98 (d, J=6.0Hz, 1H).

	With cesium acetate; In DMF (N,N-dimethyl-formamide); at 80℃; for 2h;	A solution of 2,4-dichloro-3-nitropyridine (6.5 g, 33.7 mmol) and cesium acetate (16.2 g, 84.2 mmol) in 100 mL of DMF was heated at 80 C. for 2 h. The reaction was cooled to room temperature, 50 mL of sat. aq. NH4Cl was added and the mixture was concentrated. The residue was partitioned between 200 mL DCM, 100 mL sat. aq. NH4Cl and 50 mL H2O. The layers were separated and the aqueous layers was backwashed with 200 mL DCM (4×). The combined organics were dried and concentrated (high vacuum) to afford the title compound as a tan solid: 1H NMR (CD3OD) delta6.97 (d, 1H, 5.9 Hz); 8.14 (d, 1H, 5.6 Hz). MS: MH+=174.9.
		Step-III: Synthesis of 2-chloro-3-nitropyridin-4-ol from 2, 4-dichloro-3-nitro- pyridine; Charged in a R.B. flask dimethylformamide (500 ml), . 2,4-dichlo-3-nitropyridine (100 gm) and sodium acetate (102.4 gm) at 25- 300 C. Heated the reaction mass to 120 to 125C and maintained for 2 hrs. Stopped heating and cooled the reaction mass gradually to 30 to 35C. Charged saturated ammonium chloride solution (800 ml) and stirred for 1045 min. Concentrated the reaction mass at 65 to 7O0C under vacuum to get crude solid product. Charged to the residue saturated ammonium chloride solution (1600 ml) DM water (800 ml) and dichloromethane (1000 ml) and stirred for 15 minutes. Separated the organic layer and extracted the aqueous layer further with dichloromethane (4x500 ml). Combined the organic layer and concentrated under vacuum to get thick solid mass. Charged toluene (1200 ml) to the residue and stirred at 25 - 30C for 30-45 minutes. Filtered the product, washed with cold toluene (400 ml), and dried under vacuum at 40 to 45C to get 2-chloro-3-nitropyridin-4-ol. Dry wt = 45 gm (50%).
	With sodium acetate; In N,N-dimethyl-formamide; at 120℃; for 3h;Inert atmosphere;	Compound WX065-1 (35.00 g, 181.36 mmol) and sodium acetate (44.63 g, 544.08 mmol) were dissolved in N,N-dimethylformamide (600.00 mE) at room temperature. The reaction mixture was heated to 120 C. and stirred for 3 hours under nitrogen atmosphere. After the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure to remove the solvent. Ethyl acetate (500 mE) and water (200 mE) were added to the obtained residue. The organic phases were separated and the aqueous phases were extracted with ethyl acetate (200 mEx3). The organic phases were combined, washed with saturated brine (200 mE) and dried over anhydrous sodium sulfate, followed by filtration. The filtrate was concentrated under reduced pressure to remove the solvent to obtain the crude product. The obtained crude product was slurried for 30 minutes with the mixture of petroleum ether and ethyl acetate, followed by filtration. The filter cake was dried in vacuum for 30 minutes to obtain the target product WX068- 3. ?H NMR (400 MHz, DMSO_d5) oe: 8.19 (d, J=6.0 Hz, 1H), 7.03 (d, J=6.0 Hz, 1H).

References: [1]Patent: WO2017/14323,2017,A1 .Location in patent: Paragraph 0247.
[2]Patent: US2014/94456,2014,A1 .Location in patent: Paragraph 0713; 0715.
[3]Patent: WO2015/153683,2015,A1 .Location in patent: Paragraph 0477.
[4]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4411 - 4416.
[5]Patent: US2003/225131,2003,A1 .Location in patent: Page 22.
[6]Patent: WO2010/89773,2010,A2 .Location in patent: Page/Page column 16.
[7]Patent: US2019/177318,2019,A1 .Location in patent: Paragraph 0280-0281; 0284-0285.

3
[ 239482-98-5 ]
[ 629655-23-8 ]
[ 629655-36-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In ethanol; for 72h;Heating / reflux;	To a solution of tert-butyl 2-(2-aminoethyl)piperidine-1-carboxylate (1.50 g, 6.59 mmol) and <strong>[629655-23-8]2-chloro-3-nitropyridin-4-ol</strong> (0.959 g, 5.50 mmol) in 5 mL of EtOH, was added DIEA (1.50 mL, 8.25 mmol). The reaction was refluxed at 78 C. for 3 days, diluted with 200 mL of DCM, washed with 100 mL of saturated sodium bicarbonate solution (2×0 and concentrated. The residue was purified with 10% MeOH-DCM to give the title comnpound: 1H NMR (CDCl3) delta1.36-1.71 (m, 16H), 2.05-2.15 (b, 1H), 2.76-2.84 (t, 1H), 3.37 (b, 1H), 3.80 (b, 1H), 4.00 (b, 1H ), 4.39 (b, 1H), 6.24-6.25 (d, 1H, 5.5 Hz), 8.06-8.08 (d, 1H, 5.5 Hz), 12.4 (b, 1H). MS: MH+=367.

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4411 - 4416.
[2]Patent: US2003/225131,2003,A1 .Location in patent: Page 24.

4
[ 89282-12-2 ]
[ 629655-23-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4411 - 4416.
[2]Patent: US2014/94456,2014,A1 .
[3]Patent: WO2015/153683,2015,A1 .
[4]Patent: WO2017/14323,2017,A1 .

5
[ 629655-23-8 ]
[ 629655-37-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4411 - 4416.

6
[ 629655-23-8 ]
2-[5-chloro-2-(1H-1,2,4-triazol-1-yl)benzyl]-N-(2-piperidin-2-ylethyl)[1,3]oxazolo[4,5-c]pyridin-4-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4411 - 4416.

7
[ 629655-23-8 ]
[ 629655-39-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4411 - 4416.

8
[ 629655-23-8 ]
[ 629655-38-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4411 - 4416.

9
[ 629655-23-8 ]
[ 656237-78-4 ]