56291-51-1|N3-Methylpyridine-2,3-diamine| Ambeed

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Quality Control of [ 56291-51-1 ] Purity: 97% SDS Specification

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Product Details of [ 56291-51-1 ]

CAS No. :	56291-51-1
Formula :	C₆H₉N₃
M.W :	123.16
SMILES Code :	NC1=NC=CC=C1NC
MDL No. :	MFCD00490112
InChI Key :	TZRRONMICPMDGT-UHFFFAOYSA-N
Pubchem ID :	12238404

Safety of [ 56291-51-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 56291-51-1 ]

* 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 [ 56291-51-1 ]

[ 56291-51-1 ] Synthesis Path-Downstream 1~36

1
[ 18364-47-1 ]
[ 56291-51-1 ]

References: [1]Roczniki Chemii,1935,vol. 15,p. 365,370.
Chemisches Zentralblatt,1936,vol. 107,p. 1219.

2
[ 40932-43-2 ]
[ 56291-51-1 ]

References: [1]Journal of the Chemical Society, <1957> 442, 446,.

3
[ 32605-06-4 ]
[ 56291-51-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogen;palladium 10% on activated carbon; In methanol; 1,2-dimethoxyethane; for 7h;	N-Methyl-2-nitropyridin-3-amine (14.1 g, 0.092 mol) was suspended under vigorous stirring in 1 ,2-dimethoxyethane/methanol mixture (1 :1 , 400 mL). The reaction apparatus was flushed with dry nitrogen. The catalyst (Pd/C 10%, 1.4 g) was added to the mixture. Hydrogen was bubbled through the suspension for 7 h. The reaction mixture was diluted with chloroform (300 mL) and passed through a filter with Celite (upper layer, 3 cm) and silica gel (lower layer, 5 cm, diameter 13 cm) to remove the catalyst. The layers were washed with chloroform/methanol mixture (1:1, 500 mL). The solvent was removed under reduced pressure, and the residue was mixed with acetonitrile. The mixture was concentrated under reduced pressure to give N-Methylpyridine-2,3-diamine (11.05 g, 97%, 0.09 mol). The product was used for the next stage without additional purification.
	With hydrogen;palladium on activated charcoal; In methanol; for 4h;	Step 2: N3-methylpyridine-2,3-diamineN-methyl-2-nitropyridin-3-amine (535 mg, 3.49 mmol) was dissolved in MeOH (50 ml) and treated with Pd-C (100 mg, 0.094 mmol). The solution was placed under a positive pressure of H2 for 4 hours and then filtered. The filtrate was concentrated in vacuo to afford the title compound which was used in the next step without further purification; 1H NMR (400MHz, DMSO) δ 7.28 (1 H, m), 6.50 (2H, m), 5.36 (2H, s), 4.84 (1 H, m), 2.69 (3H, d).

References: [1]Heterocyclic Communications,2013,vol. 19,p. 327 - 330.
[2]Patent: WO2008/12622,2008,A2 .Location in patent: Page/Page column 58.
[3]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5493 - 5496.
[4]Roczniki Chemii,1935,vol. 15,p. 365,370.
Chemisches Zentralblatt,1936,vol. 107,p. 1219.
[5]Journal of the Chemical Society, <1957> 442, 446,.
[6]Journal of the Korean Chemical Society,2013,vol. 57,p. 361 - 364.
[7]Australian Journal of Chemistry,2016,vol. 69,p. 618 - 630.
[8]Journal of Organic Chemistry,2017,vol. 82,p. 9243 - 9252.
[9]Patent: WO2011/92293,2011,A1 .Location in patent: Page/Page column 94.

4
[ 98961-03-6 ]
[ 56291-51-1 ]

References: [1]Journal of the Chemical Society, <1957> 442, 446,.

5
[ 61127-23-9 ]
[ 56291-51-1 ]
(1-methyl-2-oxo-1,2-dihydro-pyrido[2,3-<i>b</i>]pyrazine-3-carbonyl)-urea [ No CAS ]

References: [1]Journal of the Chemical Society,1957,p. 430,434.

6
[ 56291-51-1 ]
[ 609-09-6 ]
[ 1471-84-7 ]

References: [1]Journal of the Chemical Society,1957,p. 430,434.

7
[ 108-30-5 ]
[ 56291-51-1 ]
[ 123494-82-6 ]

References: [1]Pharmazie,1989,vol. 44,p. 267 - 269.

8
[ 75-15-0 ]
[ 56291-51-1 ]
[ 120759-61-7 ]

References: [1]Chemistry of Heterocyclic Compounds,1988,p. 653 - 658.
Khimiya Geterotsiklicheskikh Soedinenii,1988,vol. 24,p. 799 - 804.

9
[ 75-44-5 ]
[ 56291-51-1 ]
[ 50339-06-5 ]

References: [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 1709 - 1716.

10
[ 78647-31-1 ]
[ 56291-51-1 ]
[ 82619-61-2 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 391 - 413.

11
[ 328-50-7 ]
[ 56291-51-1 ]
[ 156095-50-0 ]

References: [1]Il Farmaco,1994,vol. 49,p. 259 - 265.

12
[ 24424-99-5 ]
[ 56291-51-1 ]
[ 103432-67-3 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 1061 - 1064.

13
[ 56291-51-1 ]
[ 140-89-6 ]
[ 120759-61-7 ]

References: [1]Chemistry of Heterocyclic Compounds,1988,p. 653 - 658.
Khimiya Geterotsiklicheskikh Soedinenii,1988,vol. 24,p. 799 - 804.

14
[ 56291-51-1 ]
[ 611-10-9 ]
[ 116708-41-9 ]
[ 116708-40-8 ]

References: [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 1709 - 1716.
[2]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 1709 - 1716.

15
[ 56291-51-1 ]
[ 105-56-6 ]
[ 133466-04-3 ]
[ 133466-13-4 ]

References: [1]Pharmazie,1990,vol. 45,p. 904 - 907.

16
[ 99314-92-8 ]
[ 56291-51-1 ]

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 313 - 318.
[2]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1641 - 1649.

17
[ 79-14-1 ]
[ 56291-51-1 ]
[ 172648-00-9 ]
[ 175399-50-5 ]

References: [1]Pharmazie,1996,vol. 51,p. 27 - 30.

18
[ 56291-51-1 ]
2-oxocyclopentanecarboxylate [ No CAS ]
[ 116708-40-8 ]
9-Methyl-1,4,9,10-tetrahydro-2H-4,5,9-triaza-benzo[f]azulen-3-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 1643 - 1644.

19
[ 56291-51-1 ]
2-oxocyclopentacarboxylate [ No CAS ]
[ 116708-40-8 ]
9-Methyl-1,4,9,10-tetrahydro-2H-4,5,9-triaza-benzo[f]azulen-3-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 1643 - 1644.

20
[ 56291-51-1 ]
[ 76742-48-8 ]
[ 958254-65-4 ]

Yield	Reaction Conditions	Operation in experiment
39.5%		N-Methylpyridine-2,3-diamine (11.0 g, 0.089 mol) was dissolved in 1 ,2- dimethoxyethane (300 mL). Methyl 2,2-diethoxyethanimidoate (31.0 g, 0.19 mol) and glacial acetic acid (1O mL) were added to the solution under stirring. The obtained mixture was stirred at room temperature for 3 h, then refluxed for 5 h. p-Toluenesulfonic acid monohydrate (0.1 g) was added to the reaction mixture, which was refluxed for 7 h. The mixture was concentrated under reduced pressure, and the residue was diluted with toluene (300 mL). The mixture was refluxed for 7 h, cooled, and mixed with a solution of Na2CO3 (20 g) in water (500 mL). The product was extracted with ethyl acetate (3 x 300 mL) and chloroform (400 mL). The combined extracts were dried over MgSO4 and concentrated under reduced pressure to give a dark brown solid, which was chromatographed on silica gel <n="61"/>(ch)oroform/1,2-dimethoxyethane 1:1, 900 mL). 2-(diethoxymethyl)-1-methyl-1H-imidazo[4,5- b]pyridine was obtained (8.3 g, 39.5%, 0.35 mol).
39.5%		N2-methylpyridine-2,3-diamine(A3,1.1g,8.9mM)wasdissolvedin1,2-dimethoxyethane(30 ml).A2(3.1g,19mM)andglacialaceticacid(1ml)wereaddedtothesolutionunderstirring. Thereactionmixturewasstirredatroomtemperaturefor3h,andwasrefluxedfor5h.p- Toluenesulfonicacidmonohydrate(cat.)wasthenaddedtothereactionmixture,whichwas refluxedfor7h.Themixturewasconcentratedunderreducedpressure,andtheresiduewas dilutedwithtoluene(30mL).Themixturewasrefluxedfor7h,cooled,andmixedwithasolution ofsodiumcarbonate(2g)inwater(50mL).Thecrudeproductwasextractedwithethylacetate. Thecombinedextractwasdriedovermagnesiumsulfateandconcentratedunderreduced pressuretogiveadarkbrownsolid,whichwaspurifiedbysilica-gelcolumnchromatographyto obtain2-(diethoxymethyl)-1-methyl-1H-imidazo[4,5-b]pyridine(A4,0.83g,3.5mM)in39.5% yield.A4(0.83g,3.5mM)wasmixedundervigorousstirringwith4NHydrochloricacidsolution (5ml).Thereactionmixturewasstirredat58Cfor3handthenwasevaporatedtodryness.The residuewasmixedwithdioxane(15mL),andconcentratedunderreducedpressuretoremove residualwater.Thecrudeproductwaspurifiedbysilica-gelcolumnchromatographytogive1- methyl-1H-imidazo[4,5-b]pyridine-2-carbaldehyde(A,0.55g,3.4mM)in97%yield.

References: [1]Patent: WO2008/12622,2008,A2 .Location in patent: Page/Page column 58-59.
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5493 - 5496.
[3]Patent: WO2021/155196,2021,A1 .Location in patent: Page/Page column 74-75.

21
[ 56291-51-1 ]
4,5,5a,8-tetrahydro-13 methyl-2,7-dioxo-13H-cyclopenta[e]imidazo[2,1-c]pyrano[3,2-f]pyrido[3,2-b][1,4]diazepin-9-ium chloride [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 1643 - 1644.
[2]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 1643 - 1644.

22
[ 56291-51-1 ]
[ 175399-54-9 ]