872355-52-7|Methyl 6-amino-2-methylnicotinate| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 872355-52-7 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 872355-52-7 ]

CAS No. :	872355-52-7
Formula :	C₈H₁₀N₂O₂
M.W :	166.18
SMILES Code :	O=C(OC)C1=C(C)N=C(N)C=C1
MDL No. :	MFCD08062965
InChI Key :	FTEVWMZAZULDPG-UHFFFAOYSA-N
Pubchem ID :	55252884

Safety of [ 872355-52-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 872355-52-7 ]

* 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 [ 872355-52-7 ]

[ 872355-52-7 ] Synthesis Path-Downstream 1~23

1
[ 67-56-1 ]
[ 680208-82-6 ]
[ 872355-52-7 ]

Yield	Reaction Conditions	Operation in experiment
0.82 g	With sulfuric acid; for 18h;Reflux;	[0246] Preparation Example 36: Preparation of methyl 6-amino-2-methylnicotinate[0247][0248] 6-Amino-2-methylnicotinic acid (1.00 g) was suspended in methanol (15 mL), concentrated sulfuric acid (0.5mL) was added, and the mixture was stirred with heating under reflux for 18 hr. The reaction mixture was cooled, aqueoussodium hydroxide solution was added, and the mixture was extracted with chloroform. The organic layer was washedwith saturated brine, and the solvent was evaporated to give the title compound (0.82 g).MS (ESI) m/z:167(M+H)+.
		The 6-Amino-2-methyl-nicotinic acid (5.8 g) was dissolved in methyl alcohol (10OmL) and then cooled to 0 0C in an ice-water bath. Thionyl chloride (9 mL) was then added to the solution. The reaction mixture was refluxed for 8 h. After evaporating the methanol, the residue was neutralized with saturated solution of sodium bicarbonate and was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate and filtered. The filtrate was concentrated to give 4.46 g of the ester (Rf: 0.473 min, Condition B, M+H+: 167).

References: [1]Patent: EP2565182,2013,A1 .Location in patent: Paragraph 0246; 0247; 0248.
[2]Patent: WO2006/112828,2006,A1 .Location in patent: Page/Page column 74.

2
[ 872355-52-7 ]
[ 680208-83-7 ]

Yield	Reaction Conditions	Operation in experiment
88.9%	With sodium periodate; iodine; In N,N-dimethyl-formamide; at 50℃; for 1.5h;	Sodium periodate (4.05 g, 18.9 mmol) and iodine (9.62 g, 37.9 mmol) were added to a solution of <strong>[872355-52-7]methyl 6-amino-2-methylnicotinate</strong> (8.40 g, 50.5 mmol) in DMF (45 ml), and the mixture was then stirred at 50 C. for 1.5 hours. The reaction mixture was added to a cold solution of 250 ml of saturated sodium thiosulphate solution in 150 ml of water. The solid formed was filtered off with suction, washed with water and dried. This gave 13.4 mg (88.9% of theory) of methyl 6-amino-5-iodo-2-methylnicotinate. HPLC-MS: log P=1.55; mass (m/z): 293.0 (M+H)+; 1H-NMR (D6-iDMSO) 2.50 (s, 3H), 3.74 (s, 3H), 6.81 (br. s, 1H), 8.25 (s, 1H).
	With sodium periodate; iodine; In N,N-dimethyl-formamide; at 60℃; for 48h;	To a N,N-dimethylformamide (20 mL) solution of 6-Amino-2-methyl-nicotinic acid methyl ester (1.65 g) was added iodine (2.02 g) and sodium metaperiodate (0.85 g). The reaction was then heated at 60 0C for 48 h. After cooling to room temperature, the reaction was poured into the solution of sodium metabisulfite. The solid thus separated was filtered, washed with water and dried under high vacuum overnight (Yield: 1.8 g, Rf: 0.74 min, Condition B, M+H+: 293).

References: [1]Patent: US2015/216175,2015,A1 .Location in patent: Paragraph 0350.
[2]Patent: WO2006/112828,2006,A1 .Location in patent: Page/Page column 74.

3
[ 67-56-1 ]
[ 680208-82-6 ]
[ 64-17-5 ]
[ 872355-52-7 ]
[ 1094346-14-1 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of 6-amino-2-methylpyridine-3-carboxylic acid (1.0 g, 6.6 mmol) in ethanol (17 mL) at 0C was added thionyl chloride (1.55 mL, 21.2 mmol). The mixture was warmed to room temperature and then heated to 70C for 18 hours. The reaction mixture was then cooled to room temperature and methanol (6 mL) was added. The reaction mixture was heated to 70C for 16 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with ethyl acetate and aqueous saturated sodium bicarbonate. The organics were separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-12% methanol/DCM, linear gradient) to afford a 1 :1 mixture of ethyl 6-amino-2-methylpyridine-3-carboxylate and methyl 6-amino-2-methylpyridine-3- carboxylate. Characterization data for ethyl 6-amino-2-methyIpyridine-3-carboxylate: MS ESI calc'd. for C9Hi3N202 [M + H]+ 181, found 181. Characterization data for methyl 6-amino-2- methylpyridine-3-carboxylate: MS ESI calc'd. for C8HnN202 [M + H]+ 167, found 167. The mixture was used in the subsequent step without further purification.

References: [1]Patent: WO2013/52394,2013,A1 .Location in patent: Paragraph 00386.

4
[ 872355-52-7 ]
[ 1094346-14-1 ]
[ 1429912-86-6 ]
[ 1429914-08-8 ]
[ 1429914-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos; In 1,4-dioxane; at 100℃; for 18h;Inert atmosphere;	To a flask containing the mixture of ethyl 6-amino-2-methylpyridine-3- carboxylate and <strong>[872355-52-7]methyl 6-amino-2-methylpyridine-3-carboxylate</strong> from Step 1 (207 mg), tert- butyl {(lS,27?)-2-[(5-bromo-6-cyanopyridin-3-yl)amino]cyclohexyl}carbamate (PrepEx 1.1) (350 mg, 0.89 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (84 mg, 0.18 mmol), Pd2(dba)3 (81 mg, 0.089 mmol), and cesium carbonate (577 mg, 1.77 mmol) was added degassed dioxane (9 mL) and the flask was evacuated and backfilled with argon 5 times. The reaction mixture was heated to 100C for 18 hours. The reaction mixture was allowed to cool to room temperature and diluted with ethyl acetate and water. The organics were separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-100% ethyl acetate/hexanes, linear gradient) to afford a mixture of methyl 6-[5-({(li?,25 -2-[(tert- butoxycarbonyl)amino]cyclohexyl}amino)-2-cyanopyridin-3-yl]amino}-2-methylpyridine-3- carboxylate and ethyl 6-[5-({(li?,25)-2-[(tert-butoxycarbonyl)amino]cyclohexyl}amino)-2- cyanopyridin-3-yl]amino}-2-methylpyridine-3-carboxylate that was taken on to the next step without further purification. Characterization for methyl 6-[5-({(lJl?,2S)-2-[(½rt- butoxycarbonyl)amino]cyclohexyl}amino)-2-cyanopyridin-3-yl]amino}-2-methylpyridine-3- carboxylate: MS ESI calc'd. for C25H33N604 [M + H]+ 481, found 481. Characterization for ethyl 6-[5-({(l R,2S)-2- [(tert-butoxycarbonyl)amino] cyclohexyl } amino)-2-cyanopyridin-3 - yl] amino }-2-methylpyridine-3-carboxylate: MS ESI calc'd. for C26H35N604 [M + H]+495, found 495.

References: [1]Patent: WO2013/52394,2013,A1 .Location in patent: Paragraph 00387.

5
[ 872355-52-7 ]
5-(methoxycarbonyl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid [ No CAS ]

References: [1]Patent: US2015/216175,2015,A1 .

6
[ 872355-52-7 ]
methyl 6-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate [ No CAS ]

References: [1]Patent: US2015/216175,2015,A1 .

7
[ 872355-52-7 ]
methyl 1-ethyl-6-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate [ No CAS ]

References: [1]Patent: US2015/216175,2015,A1 .

8
[ 872355-52-7 ]
N⁵-cyclopropyl-1-ethyl-6-methyl-N²-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-pyrrolo[2,3-b]pyridine-2,5-dicarboxamide [ No CAS ]

References: [1]Patent: US2015/216175,2015,A1 .

9
[ 872355-52-7 ]
1-ethyl-6-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid [ No CAS ]

References: [1]Patent: US2015/216175,2015,A1 .

10
[ 872355-52-7 ]
[ 119999-22-3 ]
methyl 6-((3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino)nicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene;Inert atmosphere; Reflux;	General procedure: To a solution of compound 42 (1.7092 g, 7.86 mmol), compound 37 (2.1030 g, 8.03 mmol), CsCO3 (6.24 g, 19.2 mmol), and rac-BINAP (0.3836 g, 0.616 mmol) in toluene (9.0 mL) in a 100 mL round-bottomed flask was added Pd2(dba)3 (0.3596 g, 0.20 mmol). The solution was sparged with nitrogen for 5 minutes, then a reflux condenser was fitted to the flask, the atmosphere was evacuated and back-filled with nitrogen (three times), and the reaction was heated to reflux with stirring in an oil bath (125-120 C.) for 22 hours. After cooling the reaction to room temperature, excess cesium carbonate and other solid particulates were filtered and washed with ethyl acetate, and the organic filtrate was concentrated in vacuo to give a crude product that was purified by column chromatography (150 mL SiO2, 3.5% ethyl acetate:hexanes) to give compound 43 (2.2557 g, 81%) as a crystalline solid, m.p. 132-147 C.

References: [1]Patent: US2018/207156,2018,A1 .Location in patent: Paragraph 0114; 0132; 0137.

11
[ 872355-52-7 ]
6-[5-({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclohexyl}amino)-2-carbamoylpyridin-3-yl]amino}-2-methylpyridine-3-carboxylic acid trifluoroacetic acid [ No CAS ]

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

12
[ 872355-52-7 ]
6-[(5-[(1R,2S)-2-aminocyclohexyl]amino}-2-carbamoylpyridin-3-yl)amino]-2-methylpyridine-3-carboxylic acid trifluoroacetic acid [ No CAS ]

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

13
[ 872355-52-7 ]
[ 1429914-11-3 ]

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

14
[ 872355-52-7 ]
[ 1429912-31-1 ]

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

15
[ 42753-71-9 ]
[ 872355-52-7 ]