79055-62-2|2-Chloro-5-methylpyridin-4-amine| Ambeed

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Quality Control of [ 79055-62-2 ] Purity: 95% SDS Specification

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Product Details of [ 79055-62-2 ]

CAS No. :	79055-62-2
Formula :	C₆H₇ClN₂
M.W :	142.59
SMILES Code :	NC1=CC(Cl)=NC=C1C
MDL No. :	MFCD11977435
InChI Key :	CJGKOPNIXJWHKF-UHFFFAOYSA-N
Pubchem ID :	12643706

Safety of [ 79055-62-2 ]

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

Computational Chemistry of [ 79055-62-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.17
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	38.62
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.91 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.44
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	1.5
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.63
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.	0.75
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	1.74
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.41

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.16
Solubility	0.981 mg/ml ; 0.00688 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.	-1.92
Solubility	1.7 mg/ml ; 0.0119 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	-2.64
Solubility	0.324 mg/ml ; 0.00227 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	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.	-6.1 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)	1.52

Application In Synthesis of [ 79055-62-2 ]

* 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.

Downstream synthetic route of [ 79055-62-2 ]

[ 79055-62-2 ] Synthesis Path-Downstream 1~35

1
[ 60323-96-8 ]
[ 79055-62-2 ]

Yield	Reaction Conditions	Operation in experiment
77.63%	With hydrogenchloride; iron; In ethanol; at 60 - 65℃; for 0.5h;	In a flask, 107 mL of 80% ethanol and 30 g of the product of Step 2, The temperature was raised to 60 C, HCl was added, and Fe powder was added in batches. The temperature was controlled at 60-65 C. After the addition, the reaction was carried out for about 30 min, and the reaction was monitored by TLC under the following conditions: EpsilonAlpha:CH2Cl2 = 1:5. After the reaction, the solution was cooled to room temperature, adjusted to pH 8 with NaOH solution, and then filtered and dried. With 4 times the volume of dichloromethane temperature reflux dissolved to clarify, down to room temperature, adding petroleum ether in 17 g white product, the yield was 77.63%.
	With iron; acetic acid; at 100℃; for 0.333333h;	Iron (1.0 g) was added to a solution of 2-chloro-5-methyl-4-nitropyridine N-oxide (500 mg, 2.6 mmol) in glacial acetic acid (10 mL). The reaction mixture was then heated at 100 C for 20 minutes. The suspension was poured onto aqueous NaOH (1M) and extracted with ethyl acetate. After drying over Na2S04, the solvent was then evaporated and the title compound was isolated as a colorless solid (370 mg, 2.6 mmol, HPLC Rt 1.3 min, FIA ES+ 143.0).
	With iron; acetic acid; at 100℃; for 0.333333h;	4-Amino-2-chloro-5-methylpyridine (11) : Iron (1. 0 g) was added to a solution of 10 (500 mg, 2.6 mmol) in glacial acetic acid (10 mL). The reaction mixture was then heated at 100 C for 20 minutes. The suspension was poured on aqueous NaOH 1M and extracted with ethyl acetate. After drying over Na2SO4, the solvent was then evaporated and 11 was isolated as a colorless solid (370 mg, 2.6 mmol, HPLC Rt 1.3 min, FIA ES+ 143.0).

With iron; acetic acid; In tetrahydrofuran; methanol; at 30 - 80℃; for 0.666667h;

To a mixture of 2-chloro-5-methyl-4-nitropyridine 1 -oxide (50 g, 265 mmol) in acetic acid (200 mL) was added iron (74.0 g, 1326 mmol) at 30 C. The solution was stirred at 80 C for 40 min. The mixture was poured into aq. NaOH (1M, 4000 mL) and extracted with EtOAc (1000 mL x 3). The combined organic layers were washed with brine (800 mL), dried over anhydrous Na2S04 and filtered. The filtrate was concentrated in vacuum to give 2-chloro-5- methylpyridin-4-amine as a light yellow oil, which was used directly without further purification. MS: 143 (M + 1). 1H MR (400 MHz, d4-methanol) delta 7.65 (s, 1H), 6.55 (s, 1H), 2.03 (s, 3H).

References: [1]Patent: CN103193704,2016,B .Location in patent: Paragraph 0025; 0035-0039.
[2]Patent: WO2005/100342,2005,A1 .Location in patent: Page/Page column 24; 39.
[3]Patent: WO2003/91246,2003,A1 .Location in patent: Page/Page column 49.
[4]Patent: WO2019/94311,2019,A1 .Location in patent: Page/Page column 43; 47.

2
[ 79055-62-2 ]
[ 867279-13-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 65℃; for 0.166667h;	CuBr2 (984 mg, 4.4 mmol, 2.0 equiv. ) and tert-butylnitrite (0.5 mL) were mixed in acetonitrile (4 mL). The resulting mixture was heated at 65 C for 20 minutes and 4-amino-2-chloro-5- methylpyridine (320 mg, 2.2 mmol, 1.0 equivalent) was then added and the resulting mixture was stirred for 10 minutes at 65 C. The reaction mixture was poured on water and extracted with ethyl acetate. The organic layer was washed with NH40H until no blue color was observed in the aqueous layer. After washing with water, the organic extract was dried over Na2S04 and the solvent was removed under reduced pressure. The crude residue was purified by preparative TLC on Si02 (dichloromethane) to afford the title compound as a colorless oil (170 mg, 0.8 mmol, HPLC Rt 6.709 min, FIA ES+ 205.9, 207.9, ES- 205.9).
	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 0 - 30℃; for 13h;	To a mixture of tert-butyl nitrite (150 mL, 1262 mmol) in acetonitrile (1000 mL) was added copper(II) bromide (226 g, 1010 mmol) at 30 C. The solution was then stirred at 22 C for 40 min and then cooled to 0 C. A solution of <strong>[79055-62-2]2-chloro-5-methylpyridin-4-amine</strong> (120 g, 842 mmol) in acetonitrile (500 mL) was added at 0 C. The reaction was stirred at 0 C for 1 h and then warmed to 22 C and stirred for 12 h. The resulting mixture was concentrated in vacuum. The residue was dissolved in DCM (2000 mL), washed with aqueous NH3 (15%, 2000 mL), dried over anhydrous Na2S04, and filtered. The filtrate was concentrated in vacuum and the resulting residue was purified by flash silica gel chromatography (eluting with ethyl acetate/pet. ether gradient) to give 4-bromo-2-chloro-5-methylpyridine as colorless oil. MS: 206 / 208 (M + 1 / M + 3). 1H MR (400 MHz, CDC13) delta 8.14 (s, 1H), 7.48 (s, 1H), 2.30 (s, 3H).

References: [1]Patent: WO2005/100342,2005,A1 .Location in patent: Page/Page column 24; 39-40.
[2]Patent: WO2019/94311,2019,A1 .Location in patent: Page/Page column 43; 47; 48.

3
[ 79055-62-2 ]
[ 98-80-6 ]
[ 620616-00-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; benzene; for 16h;Heating / reflux;	4-Amino-5-methyl-2-phenylpyridine (12) : Phenylboronic acid (188 mg, 1.5 mmol, 1. 1 equiv. ) and 11 (200 mg, 1.4 mmol, 1.0 equiv.) were dissolved in benzene (5 mL). Aqueous Na2CO3 (1 mL) was then added, followed by Pd (PPh3) 4 (324 mg, 0.28 mmol, 0.2 equiv. ). The resulting mixture was refluxed for 16 hours. The reaction mixture was dissolved in ethyl acetate and washed with water. The organic extract was dried over Na2S04 and the solvent evaporated. The crude material was purified by reverse phase HPLC (Acetonitrile/water/TFA), to give 12 as a colorless solid (160 mg, 0.87 mmol, HPLC Rt 3.373 minutes ; FIA ES+ 185.1, ES-not observed).

References: [1]Patent: WO2003/91246,2003,A1 .Location in patent: Page/Page column 49.

4
[ 79055-62-2 ]
[ 76-05-1 ]
5-chloro-2-fluorophenylboronic acid [ No CAS ]
2-(5-chloro-2-fluorophenyl)-5-methylpyridin-4-amine trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43.5%		[0095] Preparation 4: 2-(5-chloro-2-fluorophenyl)-5-methylpyridin-4-amine[0096] 2-Chloro-5-methylpyridin-4-amine (180mg, 1.262 mmol), 5-chloro-2- fluorophenylboronic acid (220 mg, 1.262 mmol) and Pd(PPh3)4 (365 mg, 0.316 mmol) were combined in dioxane (4mL) and saturated K2C03 solution (2 mL). The mixture was heated at 120 °C for 30 minutes using a microwave. Solvent was removed and the reaction mixture was purified by preparative HPLC eluting with a gradient of 5 - 40percent acetonitrile (containing 0.035percent TFA) in water (containing 0.05percent TFA) using a Sunfire Prep 5muiotaeta C18, 75 X 30 mm column to give the title compound as a TFA salt (130mg, 43.5 percent yield). ESI-MS:m/z 236.1(M+H).

References: [1]Patent: WO2011/146287,2011,A1 .Location in patent: Page/Page column 18.

5
[ 79055-62-2 ]
2,5-difurorboronic acid [ No CAS ]
[ 1350649-06-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; at 95℃;	[0300] Example 96: N-(2-(2,5-difluorophenyl)-5-methylpyrimidin-4-yl)-lH-pyrazolo[4,3- 3/4]pyridin-7-amine[0301] Bis(triphenylphosphine)palladium chloride (0.733 g, 1.045 mmol), 2-chloro-5- methylpyrimidin-4-amine (1.5 g, 10.45 mmol), Na2CC>3 (5.22 mL, 10.45 mmol) and 2,5- difluorophenylboronic acid (2.145 g, 13.58 mmol) were combined and heated at 95°C overnight. The reaction was filtered warm through a pad of Celite.(R)., the solids rinsed with dioxane (3 x 25 mL) and the filtrate was concentrated directly onto a silica chromatography column which was then eluted with EtOAc (0 - 100percent) in hexanes afforded 2-(2,5- difluorophenyl)-5-methylpyrimidin-4-amine. 1H NMR (400 MHz, DMSO- 6) delta ppm 2.03 (d, J=0.76 Hz, 3 H) 6.82 (br. s., 2 H) 7.26 - 7.33 (m, 2 H) 7.57 - 7.64 (m, 1 H) 8.06 (d, J=0.76 Hz, 1 H). MS [M+H] found 222.2.

References: [1]Patent: WO2011/146287,2011,A1 .Location in patent: Page/Page column 92.

6
[ 79055-62-2 ]
[ 1350646-90-0 ]

References: [1]Patent: WO2011/146287,2011,A1 .

7
[ 79055-62-2 ]
[ 1350649-08-9 ]
[ 1350649-07-8 ]

References: [1]Patent: WO2011/146287,2011,A1 .

8
[ 79055-62-2 ]
[ 1350646-91-1 ]

References: [1]Patent: WO2011/146287,2011,A1 .

9
[ 675-10-5 ]
[ 79055-62-2 ]
[ 1380324-08-2 ]