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Quality Control of [ 98400-69-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 98400-69-2 ]

SDS Specification

Alternatived Products of [ 98400-69-2 ]

Product Details of [ 98400-69-2 ]

CAS No. :	98400-69-2	MDL No. :	MFCD02179232
Formula :	C₁₀H₁₄N₂O₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	DRZYCRFOGWMEES-UHFFFAOYSA-N
M.W :	194.23	Pubchem ID :	9990210
Synonyms :

Safety of [ 98400-69-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280	UN#:
Hazard Statements:	H302-H317	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 98400-69-2 ]

* 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 [ 98400-69-2 ]
Downstream synthetic route of [ 98400-69-2 ]

[ 98400-69-2 ] Synthesis Path-Upstream 1~3

1
[ 124-38-9 ]
[ 98400-69-2 ]
[ 171178-34-0 ]

Yield	Reaction Conditions	Operation in experiment
35%	Stage #1: With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 0.5 h; Inert atmosphere Stage #2: at -78 - 20℃; for 2 h;	To a stirred solution of BL (12 g, 0.06 mol) in dry THF (200 mL) under inert atmosphere was added n-butyl lithium (79.12 mL, 0.18 mol) at -78 °C. The reaction was warmed to 0 °C and stirred for 30 min. Carbon dioxide gas was added to the reaction mass at -78 °C for 1 h, then at RT for 1 h. The reaction was monitored by TLC. After complete consumption of the starting material, the reaction mass was diluted with water (200 mL) and washed with diethyl ether (2x150 mL). The aqueous layer was acidified with citric acid to pH~4. The obtained solid was filtered and dried under vacuum to afford BM (5.1 g, 35percent) as a white solid. *H NMR (400 MHz, DMSO-i: δ 11.76 (br s, 1H), 8.96 (s, 1H), 8.52 (d, / = 15.0 Hz, 1H), 8.22 (d, / = 15.0 Hz, 1H), 1.49 (s, 9H).
30%	Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -40 - 20℃; for 0.333333 h; Stage #2: at -78 - 20℃; for 3.25 h;	-Buli (1.6 M soln, 155 mL, 249 mmol) was added to a stirred solution of TMEDA (37.36 mL, 249 mmol) in THF AT-40 °C. The solution was allowed to come at room temperature over 10 min and stirred for another 10 min. The solution was cooled TO-78 °C. A solution OF PYRIDINE-4-YL-CARBAMIC acid-tert-butyl ester (117) (22 g, 113.26 mmol) in THF was added slowly. The solution was allowed to come at room temperature within 3 h. After stirring at room temperature for 15 min the solution was again cooled to -78 OC and a freshly crushed dry ice was added. The solution was allowed to come at room temperature, stirred for 30 min and poured into ice cold 10 percent NH4C1 solution. The solution was basified by IN NaOH solution and washed by dichloromethane. The pH of aqueous phase was adjusted to 4 by cold 10 percent HC1 solution. The solids formed were filtered, washed by water and dried under vacuum at room temperature to yield 16.3 g (30 percent) 4-tert-butoxycarbonylamino-nicotinic acid (118) as white solids. MP: 260 °C ; 1H- NMR (DMSO-d6): d 1.49 (s, 9H), 8.23 (d, J= 6.0 Hz, 1H), 8.55 (D, J= 6.0 Hz, 1H), 8. 96 (s, 1H); EIMS M/Z 238 (M+1).

Reference： [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 16, p. 3023 - 3025
[2] Patent: WO2014/117090, 2014, A1, . Location in patent: Page/Page column 123-124
[3] Patent: WO2005/21546, 2005, A1, . Location in patent: Page/Page column 124; 207-208

2
[ 109-72-8 ]
[ 98400-69-2 ]
[ 171178-34-0 ]

Reference： [1] Patent: US5654307, 1997, A,

3
[ 594-19-4 ]
[ 98400-69-2 ]
[ 171178-34-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	With carbon dioxide In tetrahydrofuran; pentane	B. 4-(Boc-amino)pyridine-3-carboxylic Acid. To a stirring solution of 4-(Boc-amino)pyridine (1.027 g, 5.30 mmol) in THF at -36 °C (internal temperature) was added a 1.7 M solution of t-butyl lithium in pentane(6.5 mL, 11 mmol), and the rate of addition was controlled so as to keep the internal temperature below -28 °C. After an additional hour (temperature kept between -30 °C and -50 °C) carbon dioxide (g) was bubbled through the solution and the cold bath was removed. After about 15 min, the mixture was poured into ice water and the aqueous phase was washed with dichloromethane. The pH was adjusted to 4-5 with citric acid and the resulting precipitate was washed with dichloromethane and methanol and dried in vacuo to give 0.811 g (64percent) of an off-white solid. ¹H-NMR IS-MS, m/e 239.0 (m+1)

Reference： [1] Patent: EP1140905, 2003, B1,

[ 98400-69-2 ] Synthesis Path-Downstream 1~7

1
[ 124-38-9 ]
[ 98400-69-2 ]
[ 171178-34-0 ]

Yield	Reaction Conditions	Operation in experiment
35%		To a stirred solution of BL (12 g, 0.06 mol) in dry THF (200 mL) under inert atmosphere was added n-butyl lithium (79.12 mL, 0.18 mol) at -78 C. The reaction was warmed to 0 C and stirred for 30 min. Carbon dioxide gas was added to the reaction mass at -78 C for 1 h, then at RT for 1 h. The reaction was monitored by TLC. After complete consumption of the starting material, the reaction mass was diluted with water (200 mL) and washed with diethyl ether (2x150 mL). The aqueous layer was acidified with citric acid to pH~4. The obtained solid was filtered and dried under vacuum to afford BM (5.1 g, 35%) as a white solid. *H NMR (400 MHz, DMSO-i: delta 11.76 (br s, 1H), 8.96 (s, 1H), 8.52 (d, / = 15.0 Hz, 1H), 8.22 (d, / = 15.0 Hz, 1H), 1.49 (s, 9H).
30%		-Buli (1.6 M soln, 155 mL, 249 mmol) was added to a stirred solution of TMEDA (37.36 mL, 249 mmol) in THF AT-40 C. The solution was allowed to come at room temperature over 10 min and stirred for another 10 min. The solution was cooled TO-78 C. A solution OF PYRIDINE-4-YL-CARBAMIC acid-tert-butyl ester (117) (22 g, 113.26 mmol) in THF was added slowly. The solution was allowed to come at room temperature within 3 h. After stirring at room temperature for 15 min the solution was again cooled to -78 OC and a freshly crushed dry ice was added. The solution was allowed to come at room temperature, stirred for 30 min and poured into ice cold 10 % NH4C1 solution. The solution was basified by IN NaOH solution and washed by dichloromethane. The pH of aqueous phase was adjusted to 4 by cold 10 % HC1 solution. The solids formed were filtered, washed by water and dried under vacuum at room temperature to yield 16.3 g (30 %) 4-tert-butoxycarbonylamino-nicotinic acid (118) as white solids. MP: 260 C ; 1H- NMR (DMSO-d6): d 1.49 (s, 9H), 8.23 (d, J= 6.0 Hz, 1H), 8.55 (D, J= 6.0 Hz, 1H), 8. 96 (s, 1H); EIMS M/Z 238 (M+1).

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 3023 - 3025
[2]Patent: WO2014/117090,2014,A1 .Location in patent: Page/Page column 123-124
[3]Patent: WO2005/21546,2005,A1 .Location in patent: Page/Page column 124; 207-208

2
[ 98400-69-2 ]
[ 257937-08-9 ]

Yield	Reaction Conditions	Operation in experiment
52%		tert-Butyl (3-bromopyridin-4-yl)carbamate (3f) (52%) was prepared from pyridine 2f (2.70 g, 13.9 mmol) [34]. White solid; mp 91-92 C. 1H NMR (400 MHz, CDCl3) delta 8.58 (s, 1H), 8.37 (d, J=5.6 Hz, 1H), 8.15 (d, J=5.6 Hz, 1H), 7.18 (s, 1H), 1.55 (s, 9H); 13C NMR (101 MHz, CDCl3) delta 151.6, 151.4, 149.4, 143.1, 113.1, 109.6, 82.4, 28.1 (3C).

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 9430 - 9443
[2]European Journal of Medicinal Chemistry,2015,vol. 102,p. 403 - 412

3
[ 98400-69-2 ]
[ 211029-67-3 ]

Yield	Reaction Conditions	Operation in experiment
54 - 58%		n-Butyllithium (1.6 M in hexanes; 220 ml, 0.35 mol) was slowly dropwise over 30 min to a stirred solution of pyridin-4-yl-carbamic acid tert-butyl ester (26.08 g, 0.13 mol) and N,N,N,N-tetramethylethylenediamine (55 ml, 0.36 mol) in tetrahydrofuran (750 ml) at -78 C. The solution was stirred at-78 C for 15 min and 2 h at-10 C. The mixture was cooled to -78 C and a solution of iodine (95.11 g, 0.37 mol) in tetrahydrofuran (250 ml) was added dropwise over 30 min. The mixture was stirred for a further 2 h and then the mixture was quenched with water (250 ml) at 0 C. A saturated solution of sodium sulfite (100 ml) was added and the organic layer separated. The aqueous layer was extracted with dichloromethane (2 x 500 ml) and then the combined organic extracts were dried and concentrated in vacuo to give a brown oil. Purification by flash column chromatography on silica gel eluting with 20 % ethyl acetate : heptane gave (3-iodo-pyridin-4-yl)-carbamic acid tert-butyl ester (25.00 g, 58 %) as an off-white solid, No.H (400 MHz, CDC13) 8.76 (1H, s), 8.35 (1H, d J 5.7 Hz), 8.11 (1H, d J 5.7 Hz), 7.04 (lH, br s), 1.55 (9H, s) ; Tr = 0.99 min, m/z (ES+) (M+H)+ 321.08.

Reference： [1]Patent: WO2005/121141,2005,A1 .Location in patent: Page/Page column 13; 20
[2]Journal of Organic Chemistry,2004,vol. 69,p. 6772 - 6780

4
[ 109-72-8 ]
[ 98400-69-2 ]
[ 171178-34-0 ]

Yield	Reaction Conditions	Operation in experiment
54%	In tetrahydrofuran; water;	4-(N-t-Butoxycarbonylamino)nicotinic acid. n-Butyl lithium (2.18M, 24 mL, 52.51 mmol) is added slowly to a solution of 4-(N-t-butoxycarbonylamino)pyridine (4.08 g, 21 mmol) in THF (50 mL, stirred under N2 at -78 C. The solution is allowed to warm to 0 C., stirred for 3 h, then cooled again to -78 C. and poured into ether (100 mL) containing dry ice. The solution is warmed to room temperature with constant stirring. Water is added and the mixture is neutralized with acetic acid. The resulting solid is collected by vacuum filtration and dried in a vacuum oven to give 4-(N-t-butoxycarbonylamino)nicotinic acid (2.72 g, 54%) as a brown solid. 1 H NMR (DMSO) delta 11.75 (1H, brs), 8.95 (1H, s), 8.50 (1H, d, J=6.0 Hz), 8.20 (1H, d, J=6.0 Hz), 1.49 (9H, s).

Reference： [1]Patent: US5654307,1997,A

5
[ 594-19-4 ]
[ 98400-69-2 ]
[ 171178-34-0 ]

Yield	Reaction Conditions	Operation in experiment
0.811 g (64%)	With carbon dioxide; In tetrahydrofuran; pentane;	B. 4-(Boc-amino)pyridine-3-carboxylic Acid. To a stirring solution of 4-(Boc-amino)pyridine (1.027 g, 5.30 mmol) in THF at -36 C (internal temperature) was added a 1.7 M solution of t-butyl lithium in pentane(6.5 mL, 11 mmol), and the rate of addition was controlled so as to keep the internal temperature below -28 C. After an additional hour (temperature kept between -30 C and -50 C) carbon dioxide (g) was bubbled through the solution and the cold bath was removed. After about 15 min, the mixture was poured into ice water and the aqueous phase was washed with dichloromethane. The pH was adjusted to 4-5 with citric acid and the resulting precipitate was washed with dichloromethane and methanol and dried in vacuo to give 0.811 g (64%) of an off-white solid. 1H-NMR IS-MS, m/e 239.0 (m+1)

Reference： [1]Patent: EP1140905,2003,B1

6
[ 98400-69-2 ]
[ 1060812-84-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 69 - 85

7
[ 98400-69-2 ]
[ 211029-67-3 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; iodine; In tetrahydrofuran;	Reference Example 49 (3-iodo-pyridin-4-yl)-carbamic acid tert-butyl ester. To a solution of pyridin-4-yl-carbamic acid tert-butyl ester (14.8 g, 76.3 mmol) (reference example 44b) in THF (300 mL) is added N,N,N',N'-tetramethylethylene-diamine (34.5 mL, 230 mmol) and the solution cooled to -78 C. To this solution is added slowly (2.5M) n-butyllithium (91.5 mL, 230 mmol), the reaction temperature allowed to rise to -20 C. and the resulting mixture stirred for 1.5 hours. The mixture is cooled to -78 C. and a solution of iodine (29.04 g, 114 mmol) in THF (60 mL) is added then stirred for 10 min. The mixture is warmed to 20 C., stirred 30 min then diluted with ethyl acetate, washed with water, sat. sodium thiosulfate and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluding with 20% ethyl acetate in hexanes) to give 17.7 g of title compound as a light yellow crystalline solid. 1H NMR (CDCl3) delta 1.54 (s, 9H), 7.03 (bs, 1H), 8.10 (d, J=6 Hz, 1H), 8.34 (d, J=6 Hz, 1H), 8.74 (s, 1H). MS (EI) m/z 320 (M+).

Reference： [1]Patent: US6541505,2003,B1

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[ 98400-69-2 ]

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[ 259809-24-0 ]

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[ 365996-04-9 ]

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[ 1779-49-3 ]

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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

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[ CAS No. 98400-69-2 ] {[proInfo.proName]}

Quality Control of [ 98400-69-2 ]

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[ 98400-69-2 ] Synthesis Path-Upstream 1~3

[ 98400-69-2 ] Synthesis Path-Downstream 1~7

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Pyridines

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