[ CAS No. 34392-85-3 ] {[proInfo.proName]}

Name: 34392-85-3|3-Amino-2-chloro-6-methoxypyridine|98%
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SKU: A147101
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Quality Control of [ 34392-85-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 34392-85-3 ]

SDS Specification

Alternatived Products of [ 34392-85-3 ]

Product Details of [ 34392-85-3 ]

CAS No. :	34392-85-3	MDL No. :	MFCD09258809
Formula :	C₆H₇ClN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AOGGRVIJAHZLFK-UHFFFAOYSA-N
M.W :	158.59	Pubchem ID :	118674
Synonyms :

Calculated chemistry of [ 34392-85-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.14
TPSA :	48.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.75
Log Po/w (XLOGP3) :	1.44
Log Po/w (WLOGP) :	1.33
Log Po/w (MLOGP) :	0.55
Log Po/w (SILICOS-IT) :	1.27
Consensus Log Po/w :	1.27

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.11
Solubility :	1.24 mg/ml ; 0.00779 mol/l
Class :	Soluble
Log S (Ali) :	-2.06
Solubility :	1.39 mg/ml ; 0.00878 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.4
Solubility :	0.636 mg/ml ; 0.00401 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.92

Safety of [ 34392-85-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 34392-85-3 ]

* 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.

Upstream synthesis route of [ 34392-85-3 ]
Downstream synthetic route of [ 34392-85-3 ]

[ 34392-85-3 ] Synthesis Path-Upstream 1~2

1
[ 38533-61-8 ]
[ 34392-85-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: With water; tin(ll) chloride In ethyl acetate at 70℃; for 1 h; Stage #2: With sodium carbonate In water; ethyl acetate at 20℃;	Tin(ll)chloride dihydrate (6 g, 26.52 mmol) was added to a solution of 2-chloro-6-methoxy- 3-nitropyridine (1 g, 5.30 mmol) in ethyl acetate (15 ml.) and the resultant suspension heated at 70 °C with stirring for 1 h. The reaction mixture was cooled to ambient temperature, the pH adjusted to pH 9-10 by addition of saturated sodium carbonate (aq.) and extracted with ethyl acetate (3 x 5OmL). The combined extracts were dried (MgSO₄) and concentrated in vacuo to give the crude product. Purification by chromatography on silica gel with EtOAc:heptane (3:7, v/v) as eluent afforded the product as a pale yellow oil (600 mg, 72 percent). Data for S-amino-σ-chloro-e-methoxypyridine: MS (ESI) m/z: 159 ([M+H]⁺).
69%	With hydrogen In ethanol; ethyl acetate at 15 - 25℃;	A solution of 2-chloro-6-methoxy-3-nitropyridine (1.0 g, 5.3 mmol) in EtOH (50 ml)/EtOAc (50 ml) is hydrogenated at RT and 40 psi, in the presence of 10percent Pd-C (0.394 g, 0.37 mmol). The suspension is filtered through cellulose and washed with EtOH. The solution is concentrated under vacuum to give a brown oil 0.58 g (69percent yield) that is used without further purification in the next step. MS (ESI+) for C6H7ClN2O m/z 159.0 (M+H)+. Example 310 (from 2-chloro-6-methoxypyridin-3-amine and 2-isocyanato-5-(trifluoromethyl)-1,3,4-thiadiazole) is prepared by following Method C, making non-critical modifications. The solid is triturated with CH2Cl2 to give a white solid 0.104 g (47percent yield). HRMS (ESI) calcd for C10H7N5O2SClF3+H 354.0039, found 354.0046.

Reference： [1] Journal of Organic Chemistry, 2011, vol. 76, # 23, p. 9841 - 9844
[2] Organic Letters, 2016, vol. 18, # 11, p. 2774 - 2776
[3] Patent: WO2007/39563, 2007, A1, . Location in patent: Page/Page column 26
[4] Patent: US2007/112019, 2007, A1, . Location in patent: Page/Page column 13/2
[5] Patent: US2003/236287, 2003, A1, . Location in patent: Page 40
[6] Patent: WO2005/7648, 2005, A2, . Location in patent: Page 87
[7] Patent: WO2007/113548, 2007, A1, . Location in patent: Page/Page column 144

2
[ 34392-85-3 ]
[ 83732-68-7 ]

Yield	Reaction Conditions	Operation in experiment
41%	Stage #1: With hydrogenchloride; sodium nitrite In water at -5℃; for 0.333333 h; Stage #2: With copper(l) chloride In water at -5 - 20℃; for 3.41667 h; Stage #3: With sodium hydroxide In water	3-Amino-2-chloro-6-methoxypyridine (500 mg, 3.17 mmol) dissolved/suspended in cone. hydrochloric acid (10 ml.) was stirred at -5 °C while a solution of sodium nitrite (1.09 g, 15.82 mmol) in water (5 ml.) was added dropwise over 10 min. The mixture was stirred for a further 10 min before copper chloride (3.13 g, 31.65 mmol) was added portionwise over 5 min. The dark effervescing mixture was stirred at -5 °C for 20 min and then the cooling bath was removed and the mixture stirred at ambient temperature for 3 h. The mixture was diluted with water (100 ml_), basified to pH 10-1 1 by addition of 5N sodium hydroxide (aq.) and extracted with diethyl ether (3 x 5OmL). The combined extracts were washed with brine, dried (MgSO₄) and concentrated in vacuo. The crude product was purified by chromatography on silica gel with EtOAc:heptane (1 :9, v/v) as eluent to afford the product as a pale yellow oil (229 mg, 41 percent). Data for 2,3-dichloro-6-methoxypyridine: MS (ESI) m/z: 178 ([M+H]⁺).
41%	Stage #1: With hydrogenchloride; sodium nitrite In water at -5℃; for 0.333333 h; Stage #2: With copper(l) chloride In water at -5 - 20℃; for 3.41667 h; Stage #3: With sodium hydroxide In waterAlkaline aqueous solution	3-Amino-2-chloro-6-methoxypyridine (500 mg, 3.17 mmol) dissolved/suspended in conc. hydrochloric acid (10 mL) was stirred at -5 C. while a solution of sodium nitrite (1.09 g, 15.82 mmol) in water (5 mL) was added dropwise over 10 min. The mixture was stirred for a further 10 min before copper chloride (3.13 g, 31.65 mmol) was added portionwise over 5 min. The dark effervescing mixture was stirred at -5 C. for 20 min and then the cooling bath was removed and the mixture stirred at ambient temperature for 3 h. The mixture was diluted with water (100 mL), basified to pH 10-11 by addition of 5N sodium hydroxide (aq.) and extracted with diethyl ether (3 50 mL). The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica gel with EtOAc:heptane (1:9, v/v) as eluent to afford the product as a pale yellow oil (229 mg, 41percent).Data for 2,3-dichloro-6-methoxypyridine: MS (ESI) m/z: 178 ([M+H]+).

Reference： [1] Patent: WO2007/39563, 2007, A1, . Location in patent: Page/Page column 26
[2] Patent: US2007/112019, 2007, A1, . Location in patent: Page/Page column 13/2
[3] Patent: WO2005/7648, 2005, A2, . Location in patent: Page 87

[ 34392-85-3 ] Synthesis Path-Downstream 1~31

1
[ 15568-85-1 ]
[ 34392-85-3 ]
[ 952059-62-0 ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol; at 20℃; for 0.166667h;Heating / reflux;	5-(Methoxymethylidene)-2,2-dimethyl-l,3-dioxane-4,6-dione (4.69 g) was added to a solution of <strong>[34392-85-3]3-amino-2-chloro-6-methoxypyridine</strong> (4 g) in isopropanol (25 ml) at ambient temperature. The resultant mixture was stirred and heated to reflux for 10 minutes. The mixture was cooled to ambient temperature. The precipitate was isolated and washed in turn with ethyl acetate and diethyl ether. There was thus obtained 5-[(2-chloro-6-methoxypyridin- 3-ylamino)methylidene]-2,2-dimethyl-l,3-dioxane-4,6-dione (4.5 g); 1H NMR Spectrum: (CDCl3) 1.58 (s, 3H)5 1.76 (s, 3H), 3.97 (s, 3H), 6.8 (d, IH)5 7.66 (d, IH)5 8.5 (d, IH), 11.2 (s, IH).

Reference： [1]Tetrahedron,2008,vol. 64,p. 2772 - 2782
[2]Patent: WO2007/113548,2007,A1 .Location in patent: Page/Page column 144

2
[ 34392-85-3 ]
[ 50830-58-5 ]
N-(2-chloro-6-methoxy-pyridin-3-yl)-N'-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		A solution of 2-chloro-6-methoxy-3-nitropyridine (1.0 g, 5.3 mmol) in EtOH (50 ml)/EtOAc (50 ml) is hydrogenated at RT and 40 psi, in the presence of 10% Pd-C (0.394 g, 0.37 mmol). The suspension is filtered through cellulose and washed with EtOH. The solution is concentrated under vacuum to give a brown oil 0.58 g (69% yield) that is used without further purification in the next step. MS (ESI+) for C6H7ClN2O m/z 159.0 (M+H)+. Example 310 (from <strong>[34392-85-3]2-chloro-6-methoxypyridin-3-amine</strong> and 2-isocyanato-5-(trifluoromethyl)-1,3,4-thiadiazole) is prepared by following Method C, making non-critical modifications. The solid is triturated with CH2Cl2 to give a white solid 0.104 g (47% yield). HRMS (ESI) calcd for C10H7N5O2SClF3+H 354.0039, found 354.0046.

Reference： [1]Patent: US2003/236287,2003,A1 .Location in patent: Page 40

3
[ 38533-61-8 ]
[ 34392-85-3 ]

Yield	Reaction Conditions	Operation in experiment
72%		Tin(ll)chloride dihydrate (6 g, 26.52 mmol) was added to a solution of 2-chloro-6-methoxy- 3-nitropyridine (1 g, 5.30 mmol) in ethyl acetate (15 ml.) and the resultant suspension heated at 70 C with stirring for 1 h. The reaction mixture was cooled to ambient temperature, the pH adjusted to pH 9-10 by addition of saturated sodium carbonate (aq.) and extracted with ethyl acetate (3 x 5OmL). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the crude product. Purification by chromatography on silica gel with EtOAc:heptane (3:7, v/v) as eluent afforded the product as a pale yellow oil (600 mg, 72 %). Data for S-amino-?-chloro-e-methoxypyridine: MS (ESI) m/z: 159 ([M+H]+).
69%	With hydrogen;10% palladium on activated carbon; In ethanol; ethyl acetate; at 15 - 25℃; under 2068.65 Torr;	A solution of 2-chloro-6-methoxy-3-nitropyridine (1.0 g, 5.3 mmol) in EtOH (50 ml)/EtOAc (50 ml) is hydrogenated at RT and 40 psi, in the presence of 10% Pd-C (0.394 g, 0.37 mmol). The suspension is filtered through cellulose and washed with EtOH. The solution is concentrated under vacuum to give a brown oil 0.58 g (69% yield) that is used without further purification in the next step. MS (ESI+) for C6H7ClN2O m/z 159.0 (M+H)+. Example 310 (from 2-chloro-6-methoxypyridin-3-amine and 2-isocyanato-5-(trifluoromethyl)-1,3,4-thiadiazole) is prepared by following Method C, making non-critical modifications. The solid is triturated with CH2Cl2 to give a white solid 0.104 g (47% yield). HRMS (ESI) calcd for C10H7N5O2SClF3+H 354.0039, found 354.0046.
	With tin(ll) chloride; In ethyl acetate; for 16h;Heating / reflux;	Reflux a mixture of 2-CHLORO-6-METHOXY-3-NITRO-PYRIDINE (7 g, 0. 37 mol) with 3 equivalents of SNC12 (22 g, 0. 111 mol) in ethyl acetate (150 mL) for 16 hours. Partition the mixture between ethyl acetate and IN NaOH. Separate the organic layer, dry (NA2SO4) and concentrate under reduced pressure. Purify the residue by filtering through a plug of silica gel using ethyl acetate as eluent to afford the title compound.

With hydrogen;platinum(IV) oxide; In ethanol; under 988.066 Torr; for 2h;

The 4-chloro-6-methoxy-l,7-naphthyridine used as a starting material was prepared as follows :; -A mixture of 2-chloro-6-methoxy-3-nitropyridine (5 g), platinum oxide (0.25 g) and ethanol (130 ml) was stirred under 1.3 atmospheres pressure of hydrogen for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated to give 3-amino-2-chloro- 6-methoxypyridine (4.4 g); Mass Spectrum: M+H+ 159.

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 9841 - 9844
[2]Organic Letters,2016,vol. 18,p. 2774 - 2776
[3]Patent: WO2007/39563,2007,A1 .Location in patent: Page/Page column 26
[4]Patent: US2007/112019,2007,A1 .Location in patent: Page/Page column 13/2
[5]Patent: US2003/236287,2003,A1 .Location in patent: Page 40
[6]Patent: WO2005/7648,2005,A2 .Location in patent: Page 87
[7]Patent: WO2007/113548,2007,A1 .Location in patent: Page/Page column 144

4
[ 34392-85-3 ]
[ 83732-68-7 ]

Yield	Reaction Conditions	Operation in experiment
41%		3-Amino-2-chloro-6-methoxypyridine (500 mg, 3.17 mmol) dissolved/suspended in cone. hydrochloric acid (10 ml.) was stirred at -5 C while a solution of sodium nitrite (1.09 g, 15.82 mmol) in water (5 ml.) was added dropwise over 10 min. The mixture was stirred for a further 10 min before copper chloride (3.13 g, 31.65 mmol) was added portionwise over 5 min. The dark effervescing mixture was stirred at -5 C for 20 min and then the cooling bath was removed and the mixture stirred at ambient temperature for 3 h. The mixture was diluted with water (100 ml_), basified to pH 10-1 1 by addition of 5N sodium hydroxide (aq.) and extracted with diethyl ether (3 x 5OmL). The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica gel with EtOAc:heptane (1 :9, v/v) as eluent to afford the product as a pale yellow oil (229 mg, 41 %). Data for 2,3-dichloro-6-methoxypyridine: MS (ESI) m/z: 178 ([M+H]+).
41%		3-Amino-2-chloro-6-methoxypyridine (500 mg, 3.17 mmol) dissolved/suspended in conc. hydrochloric acid (10 mL) was stirred at -5 C. while a solution of sodium nitrite (1.09 g, 15.82 mmol) in water (5 mL) was added dropwise over 10 min. The mixture was stirred for a further 10 min before copper chloride (3.13 g, 31.65 mmol) was added portionwise over 5 min. The dark effervescing mixture was stirred at -5 C. for 20 min and then the cooling bath was removed and the mixture stirred at ambient temperature for 3 h. The mixture was diluted with water (100 mL), basified to pH 10-11 by addition of 5N sodium hydroxide (aq.) and extracted with diethyl ether (3 50 mL). The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica gel with EtOAc:heptane (1:9, v/v) as eluent to afford the product as a pale yellow oil (229 mg, 41%).Data for 2,3-dichloro-6-methoxypyridine: MS (ESI) m/z: 178 ([M+H]+).
		Bring a solution of 2-chloro-6-methoxy-3-nitro-pyridine (2. 8 g, 0. 018 mol) in 75% H2SO4 (15 mL) to 0C using an ice bath. Slowly add a solution of NaN02 in water (5 mL) to the reaction mixture and stir for 30 minutes. Add three molar equivalents of CuCI in concentrated HCl and stir for 15 minutes. Heat the mixture at 80C for 30 minutes. Pour onto ice, extract the aqueous with ethyl acetate, dry the organic layer (NA2SO4) and concentrate under reduced pressure. Purify using flash column chromatography (hexanes to 10% ethyl acetate/hexanes eluent) to afford the title compound.

Reference： [1]Patent: WO2007/39563,2007,A1 .Location in patent: Page/Page column 26
[2]Patent: US2007/112019,2007,A1 .Location in patent: Page/Page column 13/2
[3]Patent: WO2005/7648,2005,A2 .Location in patent: Page 87

5
[ 1352997-65-9 ]
[ 34392-85-3 ]
[ 1352997-83-1 ]

Reference： [1]Letters in drug design and discovery,2011,vol. 8,p. 972 - 979

6
[ 34392-85-3 ]
[ 75318-43-3 ]
[ 1417816-51-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 621 - 629

7
[ 34392-85-3 ]
[ 1360887-62-2 ]
[ 1417816-65-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 621 - 629

8
[ 141-32-2 ]
[ 34392-85-3 ]
[ 27017-64-7 ]