[ CAS No. 26893-72-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 26893-72-1 * Storage: {[proInfo.prStorage]}

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 26893-72-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 26893-72-1 ]

SDS Specification

Alternatived Products of [ 26893-72-1 ]

Product Details of [ 26893-72-1 ]

CAS No. :	26893-72-1	MDL No. :	MFCD00233707
Formula :	C₈H₈N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	180.16	Pubchem ID :	-
Synonyms :

Safety of [ 26893-72-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 26893-72-1 ]

* 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.

Upstream synthesis route of [ 26893-72-1 ]
Downstream synthetic route of [ 26893-72-1 ]

[ 26893-72-1 ] Synthesis Path-Upstream 1~9

1
[ 26893-72-1 ]
[ 23628-31-1 ]

Reference： [1] Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 715 - 736
[2] Patent: US6689754, 2004, B1,
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 14, p. 2238 - 2241
[4] Supramolecular Chemistry, 2010, vol. 22, # 9, p. 483 - 490
[5] Farmaco, Edizione Scientifica, 1959, vol. 14, p. 594,596
[6] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
[7] Patent: EP2017275, 2009, A1, . Location in patent: Page/Page column 153; 154

2
[ 26893-72-1 ]
[ 64-17-5 ]
[ 69142-64-9 ]

Reference： [1] Farmaco, Edizione Scientifica, 1959, vol. 14, p. 594,596
[2] European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928

3
[ 26893-72-1 ]
[ 69142-64-9 ]

Reference： [1] Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 715 - 736

4
[ 26893-72-1 ]
[ 79651-64-2 ]

Reference： [1] European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928
[2] Patent: EP3018125, 2016, A1,

5
[ 26893-72-1 ]
[ 178876-83-0 ]

Reference： [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[2] Patent: US2011/190269, 2011, A1,
[3] Patent: WO2011/92272, 2011, A1,

6
[ 26893-72-1 ]
[ 178876-83-0 ]
[ 178876-82-9 ]

Reference： [1] Patent: US2011/201605, 2011, A1,
[2] Patent: WO2011/101304, 2011, A2,

7
[ 26893-72-1 ]
[ 178876-82-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 4026 - 4030
[2] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[3] Patent: US2011/190269, 2011, A1,
[4] Patent: WO2011/92272, 2011, A1,

8
[ 26893-72-1 ]
[ 178876-83-0 ]
[ 178876-82-9 ]

Reference： [1] Patent: US2011/201605, 2011, A1,
[2] Patent: WO2011/101304, 2011, A2,

9
[ 26893-72-1 ]
[ 178876-86-3 ]

Reference： [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633

[ 26893-72-1 ] Synthesis Path-Downstream 1~10

1
[ 5327-33-3 ]
[ 26893-72-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium permanganate; water at 80℃; for 5h;
62%	With potassium permanganate; sodium hydroxide In water Reflux;
54.7%	With potassium permanganate at 75℃; for 2h;

50%	With potassium permanganate In water at 80℃; for 6h;	9.12.b Synthesis of 6-acetamidopicolinic acid (Compound 3) [1] 6-acetamidopicolinic acid(3) [1]: To a solution of N-(6-methylpyridin-2-yl)acetamide 2 (285 g, 1.90 mol) in 2.85L water was added KMnO4(750.5 g, 4.75mol) in portions during a period of 3hr at 80 °C. After stirred at 80°C for another 3h, the mixture was filtered through a pad of Celite and the Celite cake was washed with hot water (2*300ml). The filtrate was concentrated under reduced pressure to about 300ml, and acidified with 6N HCl to pH=3-3.5. The resulting precipitate was collected by filtration, dried to give white solid (171g, 50%). 1H-NMR (d6-DMSO, 300MHz): δ 0.86 (s, 3H) ; 5.96(d, 1H); 6.09 (t, 1H); 6.29(d, 1H).
48%	With potassium permanganate In water	L.A Step A Step A To a solution of 2-acetylamino-6-methylpyridine (10.0 g) in water (125 mL) at 75° C. was added KMnO4 (21.0 g) in portions and heating was continued for 2 hours. The reaction mixture was cooled, filtered and the residue washed with hot water (225 mL). The combined aqueous filtrate and the washings were washed with dichloromethane (340 mL), and acidified with cold 3 N HCl. The resulting precipitate was filtered, washed with water to neutral pH, and dried under vacuum to afford 2-acetylaminopyridine-6-carboxylic acid (3.8 g, 48% yield). The dichloromethane extract was concentrated to dryness to give the unreacted 2-acetylamino-6-methylpyridine (3.5 g). 1H-NMR (CD3OD) δ 8.32 (m, 1H), 7.94 (t, 1H), 7.87 (m, 1H), 2.2 (s, 3H); FAB MS m/z 181 (M+H).
37%	Stage #1: 2-acetylamino-6-methylpyridine With potassium permanganate In water at 75℃; for 4h; Stage #2: With hydrogenchloride In water	116.b b) 6-Acetylamino-pyridine-2-carboxylic acid; A solution of N-(6-methyl-pyridin-2-yl)-acetamide (10 g, 0.067 mmol) in water (100 mL) was heated to 75° C. Potassium permanganate (37 g, 233 mmol) was added portion-wise at 75° C. After 4 hours at 75° C. for the reaction mixture was cooled to room temperature and the solid was filtered. The aqueous layer was evaporated to half of its original volume and acidified with HCl (12N) to pH 4-5. The precipitate was filtered and dried. The title compound was obtained as off white solid (4.5 g, 37%).MS ESI (m/z): 181.2 [(M+H)+].1H NMR (DMSO, 400 MHz): δ (ppm)=13.0 (s, 1H), 10.78 (s, 1H), 8.26 (d, J=8.28 Hz, 1H), 7.92 (t, J=7.8 Hz, 1H), 7.72 (d, J=7.1 Hz, 1H), 2.10 (s, 3H).
37%	Stage #1: 2-acetylamino-6-methylpyridine With potassium permanganate In water at 75℃; for 4h; Stage #2: With hydrogenchloride In water	116.b A solution of N-(6-methyl-pyridin-2-yl)-acetamide (10 g, 0.067 mmol) in water (100 mL) was heated to 75 °C. Potassium permanganate (37 g, 233 mmol) was added portion-wise at 75°C. After 4 hours at 75 °C for the reaction mixture was cooled to room temperature and the solid was filtered. The aqueous layer was evaporated to half of its original volume and acidified with HC1 (12N) to pH 4-5. The precipitate was filtered and dried. The title compound was obtained as off white solid (4.5 g, 37%).MS ESI (nVz): 181.2 [(M+H)+].1H NMR (DMSO, 400 MHz): <5 (ppm) = 13.0 (s, 1H), 10.78 (s, 1H), 8.26 (d, J = 8.28 Hz, 1H), 7.92 (t, J= 7.8 Hz, 1H), 7.72 (d, J= 7.1 Hz, 1H), 2.10 (s, 3H).
37%	Stage #1: 2-acetylamino-6-methylpyridine With potassium permanganate; water at 75℃; for 4h; Stage #2: With hydrogenchloride In water	49.b b) 6-Acetylamino-pyridine-2-carboxylic acid; A solution of N-(6-methyl-pyridin-2-yl)-acetamide (10 g, 0.067 mmol) in water (100 mL) was heated to 75° C. Potassium permanganate (37 g, 233 mmol) was added portion-wise at 75° C. After 4 hours at 75° C. for the reaction mixture was cooled to room temperature and the solid was filtered. The aqueous layer was evaporated to half of its original volume and acidified with HCl (12 N) to pH 4-5. The precipitate was filtered and dried. The title compound was obtained as off white solid (4.5 g, 37%).MS ESI (m/z): 181.2 [(M+H)+].1H NMR (DMSO-D6, 400 MHz): (ppm)=13.0 (s, 1H), 10.78 (s, 1H), 8.26 (d, J=8.28 Hz, 1H), 7.92 (t, J=7.8 Hz, 1H), 7.72 (d, J=7.1 Hz, 1H), 2.10 (s, 3H).
37%	With potassium permanganate In water at 75℃; for 4h;	49.b A solution of N-(6-methyl-pyridin-2-yl)-acetamide (10 g, 0.067 mmol) in water (100 mL) was heated to 75 °C. Potassium permanganate (37 g, 233 mmol) was added portion-wise at 75°C. After 4 hours at 75 °C for the reaction mixture was cooled to room temperature and the solid was filtered. The aqueous layer was evaporated to half of its original volume and acidified with HC1(12 N) to pH 4-5. The precipitate was filtered and dried. The title compound was obtained as off white solid (4.5 g, 37%).MS ESI (m/z): 181.2 [(M+H)+].1H NMR (DMSO-D6, 400 MHz): (ppm) = 13.0 (s, 1H), 10.78 (s, 1H), 8.26 (d, J= 8.28 Hz,1H), 7.92 (t, J= 7.8 Hz, 1H), 7.72 (d, J= 7.1 Hz, 1H), 2.10 (s, 3H).
26%	With potassium permanganate In water for 0.583333h; Heating;
	With potassium permanganate; water
	With potassium permanganate at 75℃; for 10h;
	With potassium permanganate Yield given;
16.5 g	With potassium permanganate In water at 75℃; for 3h;
	With potassium permanganate In water at 90℃; for 6h;	8.B Step B; Preparation of 6-(acetylamino)-2-pyridinecarboxylic acid To a suspension of N-(6-methyl-2-pyridinyl) acetamide (i. e. the product of Step A) (27 g, 184 mmol) in water (250 mL) at [90 C] was added potassium permanganate (29.1 g, 184 mmol) in small portions. After the addition, the mixture was heated to [90 C] for 6 h. The mixture was then cooled and filtered through a pad of [CELITE)] diatomaceous filter aid. The filtrate was concentrated to half of its volume and acidified with concentrated hydrochloric acid. The precipitated solids were isolated by filtration and dried to give 20 g of the title compound.
	Stage #1: 2-acetylamino-6-methylpyridine With potassium permanganate In water at 75℃; for 3h; Stage #2: With hydrogenchloride In water	17b 17b) 6-Acetylamino-pyridine-2-carboxylic acidA solution of acetamide (17a) (53.3 g) in water (530 ml) washeated at 75°C until a homogenous solution was formed. Potassiumpermanganate (133 g) was then added in small portions over 1.25hours (the reaction temperature was carefully monitored with aninternal thermometer). After stirring for 3 hours at 75°C thereaction mixture was filtered through Celite while still hot.The filter cake was washed with hot water. The filtrate wasconcentrated to about 100 ml. Concentrated hydrochloric acid wasadded until a white solid formed. The white solid was collectedby filtration and dried under vacuum to give the desired product(32 g).1H NMR (300 MHz, d6-DMSO): 8: 10.85 (s, 1H), 8.26 (d, 1H), 7.97-7.72 (m, 1H), 7.73 (dd, 1H), 2.11 (s, 3H)
	With potassium permanganate; water at 75℃; for 3h;	149.2 (2) 60.6 g of the acetamide product [149-1] obtained in (1) above was dissolved in 600 mL of water at 75°C, and 175 g of potassium permanganate was added to the solution at the same temperature over 3 hours. The obtained reaction solution was filtered through Celite, and then the filtrate was concentrated. The obtained reaction mixture was neutralized with concentrated hydrochloric acid, and then concentrated to obtain a carboxylic acid product [149-2] as follows. [Show Image] The compound represented by the above Formula [149-2] was confirmed by LC-MS. mass: 181 (M+1)+.
	Stage #1: 2-acetylamino-6-methylpyridine With potassium permanganate In water Stage #2: at 75℃; for 3h;	2.b A suspension of the acetamide (2a) (53.3 g) in water (530 ml) was heated to 75° C., until a homogenous solution had formed. Potassium permanganate (133 g) was added in small portions within 1.25 hours (the reaction temperature in the reaction flask was controlled carefully). After stirring for 3 hours at 75° C., the reaction solution was filtered through Celit in hot state and rinsed again with hot water. The filtrate was concentrated to about 100 ml, and concentrated hydrochloric acid was added, until a white precipitate had formed. The white solid was separated by filtration, dried and resulted in the desired product (32 g).1H NMR (300 MHz, d6-DMSO): δ: 10.85 (s, 1H), 8.26 (d, 1H), 7.97-7.72 (m, 1H), 7.73 (dd, 1H), 2.11 (s, 3H)

Reference： [1]Basak, Debajyoti; Sridhar, Sucheta; Bera, Amal K.; Madhavan, Nandita [Organic and Biomolecular Chemistry, 2016, vol. 14, # 20, p. 4712 - 4717]
[2]Location in patent: scheme or table Frimannsson, Daniel O.; McCabe, Thomas; Schmitt, Wolfgang; Lawler, Mark; Gunnlaugsson, Thorfinnur [Supramolecular Chemistry, 2010, vol. 22, # 9, p. 483 - 490]
[3]Fukase, Koichi; Nakayama, Hideo; Kurosawa, Motohiro; Ikegaki, Toshiki; Kanoh, Takeshi; et al. [Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 715 - 736]
[4]Current Patent Assignee: SHIN NIPPON BIOMEDICAL LABORATORIES LTD - EP3018125, 2016, A1 Location in patent: Paragraph 0543-0544; 0546
[5]Current Patent Assignee: PFIZER INC - US6689754, 2004, B1
[6]Current Patent Assignee: ROCHE HOLDING AG - US2011/190269, 2011, A1 Location in patent: Page/Page column 61
[7]Current Patent Assignee: ROCHE HOLDING AG - WO2011/92272, 2011, A1 Location in patent: Page/Page column 129
[8]Current Patent Assignee: ROCHE HOLDING AG - US2011/201605, 2011, A1 Location in patent: Page/Page column 45
[9]Current Patent Assignee: ROCHE HOLDING AG - WO2011/101304, 2011, A2 Location in patent: Page/Page column 91
[10]Zafar, Abdullah; Geib, Steven J.; Hamuro, Yoshitomo; Carr, Andrew J.; Hamilton, Andrew D. [Tetrahedron, 2000, vol. 56, # 43, p. 8419 - 8427]
[11]Ferrari; Marcon [Farmaco, Edizione Scientifica, 1959, vol. 14, p. 594,596]
[12]Deady, Leslie W.; Korytsky, Olga L.; Rowe, Jeffrey E. [Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034]
[13]Janecka, Anna; Janecki, Tomasz; Shan, Si-mei; Bowers, Cyril; Folkers, Karl [Journal of Medicinal Chemistry, 1994, vol. 37, # 14, p. 2238 - 2241]
[14]Kelly, T. Ross; Lang, Fengrui [Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633]
[15]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2004/35545, 2004, A2 Location in patent: Page 37
[16]Current Patent Assignee: DEINOVE SA - WO2006/21448, 2006, A1 Location in patent: Page/Page column 52
[17]Current Patent Assignee: MERCK & CO INC - EP1754706, 2007, A1 Location in patent: Page/Page column 88
[18]Current Patent Assignee: DEINOVE SA - US2010/324030, 2010, A1 Location in patent: Page/Page column 10

2
[ 26893-72-1 ]
[ 64-17-5 ]
[ 69142-64-9 ]

Reference： [1]Farmaco, Edizione Scientifica,1959,vol. 14,p. 594,596
[2]European Journal of Inorganic Chemistry,2010,p. 1913 - 1928

3
[ 26893-72-1 ]
[ 36052-26-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: 6-acetamido-picolinic acid With hydrogenchloride In methanol for 18h; Reflux; Stage #2: With sodium hydrogencarbonate In water	49.c c) 6-Amino-pyridine-2-carboxylic acid methyl ester; A solution of 6-acetylamino-pyridine-2-carboxylic acid (16 g, 0.088 mol) in methanolic hydrochloride (4N, 50 mL) was heated to reflux for 18 hours. The reaction mixture was cooled to room temperature and evaporated. Water was added to the residue and alkalized with solid NaHCO3. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, and the solvent was evaporated. The title compound was obtained as a white solid (8 g, 59%).MS ESI (m/z): 153.0 [(M+H)+].1H NMR (DMSO-D6, 400 MHz): (ppm)=7.53 (t, J=7.52 Hz, 1H), 7.48 (d, J=7.28 Hz, 2H), 6.66 (d, J=8.04 Hz, 1H), 4.71 (s, 2H), 3.94 (s, 3H).
59%	Stage #1: 6-acetamido-picolinic acid With hydrogenchloride In methanol for 18h; Reflux; Stage #2: With sodium hydrogencarbonate In water	49.c A solution of 6-acetylamino-pyridine-2-carboxylic acid (16 g, 0.088 mol) in methanolic hydrochloride (4N, 50 mL) was heated to reflux for 18 hours. The reaction mixture was cooled to room temperature and evaporated. Water was added to the residue and alkalized with solid NaHC03. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, and the solvent was evaporated. The title compound was obtained as a white solid (8 g, 59%).MS ESI (m/z): 153.0 [(M+H)+].1H NMR (DMSO-D6, 400 MHz): (ppm) = 7.53 (t, J = 7.52 Hz, 1H), 7. 48 (d, J= 7.28 Hz, 2H), 6.66 (d, J= 8.04 Hz, 1H), 4.71 (s, 2H), 3.94 (s, 3H).
	With hydrogenchloride; methanol

With hydrogenchloride In methanol for 1h; Heating / reflux;

8.C Step C; Preparation of methyl 6-amino-2-pyridinecarboxylate Hydrogen chloride gas was bubbled through a suspension of 6- (acetylamino)- 2-pyridinecarboxylic acid (i. e. the product of Step B) (20 g) in methanol (100 mL) for 1 h. The reaction mixture was then heated to reflux overnight. Concentration followed by purification on silica gel column provided the title compound (12 g). 1H NMR (CDC13) 8 7.52 [(M,] 2H), 6.69 (d, 1H), 4.80 (br s, 2H, NH2), 3.96 (s, 3H).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2011/201605, 2011, A1 Location in patent: Page/Page column 45
[2]Current Patent Assignee: ROCHE HOLDING AG - WO2011/101304, 2011, A2 Location in patent: Page/Page column 91-92
[3]Ferrari; Marcon [Farmaco, Edizione Scientifica, 1959, vol. 14, p. 594,596]
[4]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2004/35545, 2004, A2 Location in patent: Page 37

4
[ 67-56-1 ]
[ 26893-72-1 ]
[ 36052-26-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With thionyl chloride In methanol at 50℃; for 5h;	9.12.c Synthesis of Methyl 6-aminopicolinate (Compound 4)[1] Methyl 6-aminopicolinate (4) [1] : To a solution of 6-acetamidopicolinic acid 3 (171g, 0.95ml) in methanol(1.7 L) was added dropwise SOCl2 (170g, 1.43mol) at 50 °C. After the addition the mixture was stirred for an additional 5 hour while maintaining the temperature at the same temperature. Then the solvent was removed under reduced pressure, the residue was basified with a saturated solution of sodium carbonate to pH=9-10 and extracted with dichloromethane (3*650ml). The organic layers were combined and dried with anhydrous sodium sulfate and concentrated to give yellow solid Methyl 6-aminopicolinate(115g, 80%)(Compound 4). 1H-NMR (CDCl3, 300MHz): δ 3.97 (s, 3H); 4.88 (s, 2H); 6.70 (d, 1H); 7.50 (t, 1H); 7.59 (d, 1H).
77%	With hydrogenchloride In water for 72h; Reflux;
64%	With acetyl chloride Heating;

59%	Stage #1: methanol; 6-acetamido-picolinic acid With hydrogenchloride for 18h; Reflux; Stage #2: With sodium hydrogencarbonate In water	116.c c) 6-Amino-pyridine-2-carboxylic acid methyl ester; A solution of 6-acetylamino-pyridine-2-carboxylic acid (16 g, 0.088 mol) in methanolic hydrochloride (4N, 50 mL) was heated to reflux for 18 hours. The reaction mixture was cooled to room temperature and evaporated. Water was added to the residue and alkalized with solid NaHCO3. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, and the solvent was evaporated. The title compound was obtained as a white solid (8 g, 59%).MS ESI (m/z): 153.0 [(M+H)+].1H NMR (DMSO, 400 MHz): δ(ppm)=7.53 (t, J=7.52 Hz, 1H), 7.48 (d, J=7.28 Hz, 2H), 6.66 (d, J=8.04 Hz, 1H), 4.71 (s, 2H), 3.94 (s, 3H).
59%	Stage #1: methanol; 6-acetamido-picolinic acid With hydrogenchloride for 18h; Reflux; Stage #2: With sodium hydrogencarbonate In water Alkaline conditions;	116.c A solution of 6-acetylamino-pyridine-2-carboxylic acid (16 g, 0.088 mol) in methanolic hydrochloride (4N, 50 mL) was heated to reflux for 18 hours. The reaction mixture was cooled to room temperature and evaporated. Water was added to the residue and alkalized with solidNaHC03. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, and the solvent was evaporated. The title compound was obtained as a white solid (8 g, 59%).MS ESI (m/z): 153.0 [(M+H)+].1H NMR (DMSO, 400 MHz): δ (ppm) = 7.53 (t, J = 7.52 Hz, 1H), 7. 48 (d, J = 7.28 Hz, 2H),6.66 (d, J= 8.04 Hz, 1H), 4.71 (s, 2H), 3.94 (s, 3H).
	With hydrogenchloride Heating; Yield given;
	Stage #1: methanol; 6-acetamido-picolinic acid With hydrogenchloride Heating / reflux; Stage #2: With sodium hydrogencarbonate In dichloromethane; water	17c 17c) 6-Amino-pyridine-2-carboxylic acid methyl esterAcid (17b) (18 g) was suspended in methanol saturated withgaseous hydrochloric acid. The mixture was refluxed overnightand after cooling, concentrated to dryness. The residue waspartitioned between water and dichloromethane. Solid sodiumbicarbonate was added and the layers were separated. The aqueouslayer was back extracted with dichloromethane (200 ml). Thecombined organic layers were washed with brine, dried oversodium sulfate, filtered and evaporated. The residue waspurified by flash chromatography (silica gel,dichloromethane/ethyl acetate 1:1) to give the desired product(9.64 g).XH NMR (300 MHz, CDC13) : 8: 7.52-7.41 (m, 2H) , 6.66 (dd, 1H) ,5.12 (bs, 2H), 3.91 (s, 3H)
	With hydrogenchloride In water Reflux;	2.c The acid (2b) (18 g) was suspended in methanol, saturated with HCl gas and heated overnight under reflux. After cooling, the reaction mixture was concentrated, and the residue was resuspended or redissolved, respectively, in water and dichloromethane. Solid sodium hydrogencarbonate was added and the phases were separated. The aqueous phase was extracted with dichloromethane. The combined organic phases were washed with a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, dichloromethane:acetic acid ethyl ester: 1:1) and resulted in the desired product (9.64 g).1H NMR (300 MHz, CDCl3): δ: 7.52-7.41 (m, 2H), 6.66 (dd, 1H), 5.12 (bs, 2H), 3.91 (s, 3H)

Reference： [1]Current Patent Assignee: SHIN NIPPON BIOMEDICAL LABORATORIES LTD - EP3018125, 2016, A1 Location in patent: Paragraph 0543-0544; 0547-0548
[2]Basak, Debajyoti; Sridhar, Sucheta; Bera, Amal K.; Madhavan, Nandita [Organic and Biomolecular Chemistry, 2016, vol. 14, # 20, p. 4712 - 4717]
[3]Ontoria, Jesus M.; Martin Hernando, Jose I.; Malancona, Savina; Attenni, Barbara; Stansfield, Ian; Conte, Immacolata; Ercolani, Caterina; Habermann, Joerg; Ponzi, Simona; Di Filippo, Marcello; Koch, Uwe; Rowley, Michael; Narjes, Frank [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 4026 - 4030]
[4]Current Patent Assignee: ROCHE HOLDING AG - US2011/190269, 2011, A1 Location in patent: Page/Page column 61
[5]Current Patent Assignee: ROCHE HOLDING AG - WO2011/92272, 2011, A1 Location in patent: Page/Page column 129
[6]Kelly, T. Ross; Lang, Fengrui [Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633]
[7]Current Patent Assignee: DEINOVE SA - WO2006/21448, 2006, A1 Location in patent: Page/Page column 52-53
[8]Current Patent Assignee: DEINOVE SA - US2010/324030, 2010, A1 Location in patent: Page/Page column 10

5
[ 26893-72-1 ]
[ 219511-71-4 ]
[ 849669-88-1 ]

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 1109 - 1118

6
[ 26893-72-1 ]
[ 178876-82-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4026 - 4030
[2]Journal of Organic Chemistry,1996,vol. 61,p. 4623 - 4633
[3]Patent: US2011/190269,2011,A1
[4]Patent: WO2011/92272,2011,A1

7
[ 26893-72-1 ]
[ 178876-83-0 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 4623 - 4633
[2]Patent: US2011/190269,2011,A1
[3]Patent: WO2011/92272,2011,A1

8
[ 26893-72-1 ]
[ 178876-86-3 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 4623 - 4633

9
[ 26893-72-1 ]
[ 69142-64-9 ]

Reference： [1]Journal of Carbohydrate Chemistry,1994,vol. 13,p. 715 - 736

10
[ 26893-72-1 ]
[ 178876-83-0 ]
[ 178876-82-9 ]

Reference： [1]Patent: US2011/201605,2011,A1

Same Skeleton Products

Related Products

Historical Records

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 26893-72-1 ] {[proInfo.proName]}

Quality Control of [ 26893-72-1 ]

Related Doc. of [ 26893-72-1 ]

Product Details of [ 26893-72-1 ]

Safety of [ 26893-72-1 ]

Application In Synthesis of [ 26893-72-1 ]

[ 26893-72-1 ] Synthesis Path-Upstream 1~9

[ 26893-72-1 ] Synthesis Path-Downstream 1~10

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry