36340-61-1|2-Amino-4-chloro-6-picoline| Ambeed

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Quality Control of [ 36340-61-1 ] Purity: 97% SDS Specification

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Product Details of [ 36340-61-1 ]

CAS No. :	36340-61-1
Formula :	C₆H₇ClN₂
M.W :	142.59
SMILES Code :	CC1=CC(Cl)=CC(N)=N1
MDL No. :	MFCD00800671
InChI Key :	IKKMKJOVXQEEHS-UHFFFAOYSA-N
Pubchem ID :	19050509

Safety of [ 36340-61-1 ]

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

Computational Chemistry of [ 36340-61-1 ] 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.	1.55
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	1.53
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.	1.16
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	1.52

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.18
Solubility	0.939 mg/ml ; 0.00659 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.	-1.96
Solubility	1.58 mg/ml ; 0.0111 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.	-6.08 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	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)	1.45

Application In Synthesis of [ 36340-61-1 ]

* 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 [ 36340-61-1 ]

[ 36340-61-1 ] Synthesis Path-Downstream 1~32

2
[ 823-96-1 ]
[ 116632-24-7 ]
[ 36340-61-1 ]

Yield	Reaction Conditions	Operation in experiment
23%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 120℃; for 18.0h;	To a 10% aqueous solution of dioxane (0.1 M) was added 4,6-dichloropyridin-2-amine (1.0 equiv.), trimethylboroxine (1.5 equiv.), Pd(PPh3)4 (0.10 equiv.) and K2CO3 (3.0 equiv.). The solution was heated in an oil bath to 120 C. for 18 hrs, cooled to room temperature (not all of starting material was consumed), extracted with EtOAc, dried with Na2SO4, and concentrated. The crude material was purified via SiO2 column chromatography eluting with 5% MeOH/DCM to yield 4-chloro-6-methylpyridin-2-amine as an off-white solid in 23% yield. LCMS (m/z): 143 (MH+); LC Rt=1.11 min.

References: [1]Patent: US2011/195980,2011,A1 .Location in patent: Page/Page column 15.

3
[ 36340-61-1 ]
[ 73183-34-3 ]
[ 1214242-09-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; at 120℃; for 0.5h;Microwave irradiation;	A solution <strong>[36340-61-1]4-chloro-6-methylpyridin-2-amine</strong> (1.0 equiv.), potassium acetate (3.0 equiv.), bis(pinacolato)diboron (2.0 equiv.), tricyclohexylphosphine (0.075 equiv.) and Pd2(dba)3 (0.05 equiv.) in dioxane (0.12 M) was heated at 120 C. in a microwave for 2*15 minutes. The solution was filtered through a 1 muM HPLC filter, concentrated. DME was added and the resulting solid was filtered and rinsed with CH2Cl2. The combined filtrate was concentrated and pumped to yield 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine which was used directly. LC/MS=153.0 (M+H of corresponding HetB(OH)2), LC=0.35 min.

References: [1]Patent: US2011/195980,2011,A1 .Location in patent: Page/Page column 15.

4
[ 36340-61-1 ]
[ 1214242-11-1 ]

References: [1]Patent: US2011/195980,2011,A1 .

5
[ 36340-61-1 ]
tert-butyl [(3S,4S)-3-({6-cyano-5-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridin-3-yl}amino)-1,1-dioxidotetrahydro-2H-thiopyran-4-yl]carbamate [ No CAS ]

References: [1]Patent: WO2013/52394,2013,A1 .

6
[ 36340-61-1 ]
5-[(3S,45)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-3-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carbonitrile [ No CAS ]

References: [1]Patent: WO2013/52394,2013,A1 .

7
[ 36340-61-1 ]
5-[(3S,4S)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-3-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carboxamide trifluoroacetic acid [ No CAS ]

References: [1]Patent: WO2013/52394,2013,A1 .

8
[ 288-36-8 ]
[ 36340-61-1 ]
[ 1429913-18-7 ]
[ 1429913-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; at 150℃; for 1.5h;	To <strong>[36340-61-1]4-chloro-6-methylpyridin-2-amine</strong> (100 mg, 0.701 mmol) and 1 ,2,3- triazole (0.133 mL, 2.30 mmol) in a pressure tube was added DIPEA (0.185 mL, 1.06 mmol). The reaction mixture was sealed and heated at 150C for 1.5 hours. The reaction mixture was cooled, diluted with DCM (20 mL), and washed with water (10 mL). The organics were separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was slurried in 5% methanol/ethyl acetate (5 mL) and sonicated. The mixture was filtered, and the collected solids were dried under reduced pressure to afford 6-methyl-4-(lH- l,2,3-triazol-l-yl)pyridin-2-amine. MS ESI calc'd. for C8H10N5 [M + H]+ 176, found 176. ? NMR (500 MHz, DMSO-d6) delta 8.79 (s, IH), 7.95 (s, IH), 6.90 (s, IH), 6.75 (s, IH), 6.28 (s, 2H), 2.23 (s, 3H). The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (2-20% acetone/hexanes, linear gradient) to afford 6-methyl-4-(2H- l,2,3-triazol-2-yl)pyridin-2-amine. MS ESI calc'd. for C8H10N5 [M + H]+ 176, found 176. 1H NMR (500 MHz, DMSO-d6) delta 8.12 (s, 2H), 6.95 (s, IH), 6.85 (s, IH), 6.22 (s, 2H), 2.28 (s, 3H).

References: [1]Patent: WO2013/52394,2013,A1 .Location in patent: Paragraph 00225; 00226.

9
[ 67-56-1 ]
[ 36340-61-1 ]
[ 90345-22-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate; at 130℃; for 12.0h;Inert atmosphere; Microwave irradiation;	To <strong>[36340-61-1]4-chloro-6-methylpyridin-2-amine</strong> (1.0 g, 7.0 mmol) was added sodium methoxide (25% solution in methanol, 9.2 ml, 35 mmol) under a nitrogen atmosphere. The reaction mixture was heated in a microwave at 130C for 12 hours. The reaction mixture was quenched with hydrochloric acid (1.0 M in water, 42 ml, 42 mmol), and the reaction mixture was partially concentrated under reduced pressure to remove methanol. The residue was diluted with ethyl acetate, and the pH was adjusted to ~7.5 with saturated aqueous sodium bicarbonate solution. The organics were separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography(dichloromethane/methanol with ammonium hydroxide, linear gradient) to afford 4-mefhoxy-6- methylpyridin-2-amine. MS ESI calc'd. for C7HnN20 [M + H]+ 139, found 139. 1H NMR (500 MHz, DMSO-d6) delta 5.96 (d, J= 1.5 Hz, 1H), 5.75 (d, J= 2.0 Hz, 1H), 5.70 (br s, 2H), 3.66 (s, 3H), 2.13 (s, 3H).

References: [1]Patent: WO2013/52394,2013,A1 .Location in patent: Paragraph 00242.

10
[ 110-91-8 ]
[ 36340-61-1 ]
[ 1429913-20-1 ]

Yield	Reaction Conditions	Operation in experiment
	at 150℃; for 1.5h;Inert atmosphere;	To <strong>[36340-61-1]4-chloro-6-methylpyridin-2-amine</strong> (150 mg, 1.05 mmol) in a nitrogen purged vial was added morpholine (0.917 mL, 10.5 mmol). The reaction mixture was sealed and heated at 150C for 1.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DCM (10 mL) and washed with aqueous saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-10% methanol/DCM with 1% ammonium hydroxide, linear gradient) to give 6-methyl-4- morpholinopyridin-2-amine. MS ESI calc'd. for C10H16N3O [M + H]+ 194, found 194. ? NMR (500 MHz, DMSO-d6) delta 6.00 (s, IH), 5.62 (s, IH), 5.42 (s, 2H), 3.63 (m, 4H), 3.08 (m, 4H), 2.08 (s, 3H).

References: [1]Patent: WO2013/52394,2013,A1 .Location in patent: Paragraph 00228.

11
[ 36340-61-1 ]
[ 124-40-3 ]
[ 137440-97-2 ]

Yield	Reaction Conditions	Operation in experiment
	In water; at 130℃; for 2.5h;Inert atmosphere; Microwave irradiation;	To <strong>[36340-61-1]6-amino-4-chloro-2-picoline</strong> (500 mg, 3.51 mmol) in a vial under nitrogen was added dimethylamine (40% in water, 17.5 ml, 35.0 mmol). The reaction mixture was sealed and heated at 130C in a microwave for 2.5 hours. The reaction mixture was cooled, concentrated under reduced pressure, and purified by silica gel chromatography (2-10% methanol DCM with 1% ammonium hydroxide, linear gradient) to give N4,N4,6-trimethylpyridine-2,4-diamine. MS ESI calc'd. for C8Hi4N3 [M + H]+ 152, found 152. 1H NMR (500 MHz, DMSO-d6) delta 6.15 (s, 2H), 6.02 (s, IH), 5.54 (s, IH), 2.90 (s, 6H), 2.18 (s, 3H).

References: [1]Patent: WO2013/52394,2013,A1 .Location in patent: Paragraph 00229.

12
[ 7677-24-9 ]
[ 36340-61-1 ]
[ 643-79-8 ]
[ 1575389-16-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	In acetonitrile; for 12.0h;Reflux;	General procedure: A mixture of a 2-aminopyridine (1 mmol), phthalaldehyde (2) (1 mmol), and TMSCN (3)(1 mmol) in CH3CN (10 mL) was refluxed for the appropriate amount of time.After completion of the reaction, as indicated by TLC (EtOAc/n-hexane, 4:1), themixture was filtered and the residue purified by washing with n-hexane(5 mL), and then crystallized from EtOH or CH3CN to give pure crystallineproducts 4a-i.

References: [1]RSC Advances,2014,vol. 4,p. 64169 - 64173.
[2]Tetrahedron Letters,2014,vol. 55,p. 1848 - 1850.

13
[ 13061-96-6 ]
[ 116632-24-7 ]
[ 36340-61-1 ]

Yield	Reaction Conditions	Operation in experiment
100 mg	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 18.0h;	A suspension of 4,6-dichloropyridin-2-amine (1.63 g, 10 mmol), methylboronic acid (0.6 g, 10 mmol), Cs2C03 (9.75 g, 30 mmol), and Pd(dppf)Cl2 (400 mg) in dioxane/water (4: 1, 50 mL) was stirred for 18 hours at 100 C. The reaction was diluted with water and extracted with EtOAc (50 mLx3). The combined organic layer was washed with water and brine. The resulting solution was concentrated under reduced pressure and the residue was purified via prep-HPLC to afford 4-chloro-6-methylpyridin-2-amine (100 mg) as brown solid. MS ESI calcd. For C6H7C1N2 [M + H]+ 143, found 143.

References: [1]Patent: WO2014/153280,2014,A1 .Location in patent: Paragraph 00163.

14
[ 124-41-4 ]
[ 36340-61-1 ]
[ 90345-22-5 ]

Yield	Reaction Conditions	Operation in experiment
110 mg	In dimethyl sulfoxide; at 140℃; for 18.0h;	A suspension of <strong>[36340-61-1]4-chloro-6-methylpyridin-2-amine</strong> (284 mg, 2 mmol) in DMSO (10 mL) was added sodium methanolate (540 mg, 10 mmol), and the resulting mixture was then stirred for 18 hours at 140 C. The reaction was filtered and the filtrate was purified via prep-HPLC to afford 4-methoxy-6-methylpyridin-2-amine (110 mg) as brown solid. MS ESI calcd. For C7H10N2O [M + H]+ 139, found 139.

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1929 - 1939.
[2]Patent: WO2014/153280,2014,A1 .Location in patent: Paragraph 00164.

15
[ 36340-61-1 ]
[ 1429912-08-2 ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1929 - 1939.

16
[ 36340-61-1 ]
C₂₄H₃₂N₆O₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1929 - 1939.

17
[ 36340-61-1 ]
C₂₄H₃₄N₆O₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1929 - 1939.

18
[ 36340-61-1 ]
[(3S,4S)-4-amino-1,1-dioxidotetrahydro-2H-thiopyran-3-yl]amino}-3-[(4-methoxy-6-methylpyridin-2-yl)amino]pyridine-2-carboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1929 - 1939.

19
[ 36340-61-1 ]
C₂₃H₃₀N₆O₅S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1929 - 1939.

20
[ 36340-61-1 ]
C₂₃H₃₂N₆O₆S [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1929 - 1939.

21
[ 108-24-7 ]
[ 36340-61-1 ]
N-(4-chloro-6-methylpyridin-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With dmap; at 140℃; for 3.0h;	[00357] To a solution of <strong>[36340-61-1]4-chloro-6-methylpyridin-2-amine</strong> (416 mg, 2.92 mmol) in acetic anhydride (5.89 niL) was added DMAP (3.6 mg, 0.029 mmol). The reaction mixture was allowed to stir at 140C for 3h. The reaction mixture was concentrated and purified by column chromatography to provide N-(4- chloro-6-methylpyridin-2-yl)acetamide (420 mg, 78%). LCMS (FA): m/z 185.0 (M+I-I).
78%	With dmap; at 140℃; for 3.0h;	To a solution of <strong>[36340-61-1]4-chloro-6-methylpyridin-2-amine</strong> (416 mg, 2.92 mmol) in acetic anhydride (5.89 mL) was added DMAP (3.6 mg, 0.029 mmol). The reaction mixture was allowed to stir at 140 C. for 3h. The reaction mixture was concentrated and purified by column chromatography to provide N-(4-chloro-6-methylpyridin-2-yl)acetamide (420 mg, 78%). LCMS (FA): m/z=185.0 (M+H).

References: [1]Patent: WO2015/108861,2015,A1 .Location in patent: Paragraph 00357.
[2]Patent: US2015/225422,2015,A1 .Location in patent: Paragraph 0494-0495.

22
[ 36340-61-1 ]
[ 626-43-7 ]
N<SUP>4</SUP>-(3,5-dichlorophenyl)-6-methylpyridine-2,4-diamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 1182 - 1203.

23
[ 36340-61-1 ]
4-chloro-2-fluoro-6-methylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With tetrafluoroboric acid; sodium nitrite; at 0 - 60℃; for 9.0h;	5-Bromo-2-amino-6-methylpyridine (10 kg) was dissolved in HBF4 (200 L, 48%). After the reaction was cooled to 0 C, NaNO 2 (6.8 kg) was added portionwise.After the addition was completed, the reaction was allowed to rise to room temperature. After reacting for 6 hours, the reaction was continued to 3 hours by heating to 60 C.After returning to room temperature, water (200 L) was added, followed by extraction with dichloromethane (100 L×5).The extracts were combined and dried over sodium sulfate. After concentration by filtration, the reaction product was obtained as 5-bromo-2-fluoro-6-methylpyridine (78% yield: 77%).

References: [1]Patent: CN108341769,2018,A .Location in patent: Paragraph 0021; 0023; 0029; 0030.

24
[ 36340-61-1 ]
C₃₂H₄₀N₆O₃ [ No CAS ]