[ CAS No. 132521-70-1 ] {[proInfo.proName]}

Name: 132521-70-1|6-(4-Methylpiperazin-1-yl)nicotinic acid|95%
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Quality Control of [ 132521-70-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 132521-70-1 ]

SDS Specification

Alternatived Products of [ 132521-70-1 ]

Product Details of [ 132521-70-1 ]

CAS No. :	132521-70-1	MDL No. :	MFCD07376841
Formula :	C₁₁H₁₅N₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QHMVJHRGUIQPPU-UHFFFAOYSA-N
M.W :	221.26	Pubchem ID :	14987926
Synonyms :

Safety of [ 132521-70-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 132521-70-1 ]

* 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 [ 132521-70-1 ]
Downstream synthetic route of [ 132521-70-1 ]

[ 132521-70-1 ] Synthesis Path-Upstream 1~4

1
[ 132144-02-6 ]
[ 132521-70-1 ]

Reference： [1] Patent: US2009/36452, 2009, A1, . Location in patent: Page/Page column 8
[2] Patent: US2018/141923, 2018, A1, . Location in patent: Paragraph 0666; 0669; 0670

2
[ 841-77-0 ]
[ 132521-70-1 ]
[ 132521-71-2 ]

Reference： [1] Patent: US5025012, 1991, A,

3
[ 73781-91-6 ]
[ 132521-70-1 ]

Reference： [1] Patent: US2018/141923, 2018, A1,

4
[ 109-01-3 ]
[ 132521-70-1 ]

Reference： [1] Patent: US2018/141923, 2018, A1,

[ 132521-70-1 ] Synthesis Path-Downstream 1~20

1
[ 841-77-0 ]
[ 132521-70-1 ]
[ 132521-71-2 ]

Yield	Reaction Conditions	Operation in experiment
	In 1-methyl-piperazine;	6-(4-Methyl-1-piperazinyl)nicotinic acid (compound 2) and 6-(4-diphenylmethyl-1-piperazinyl)nicotinic acid (compound 3) were prepared in the same way as above using 1-methylpiperazine and 1-diphenylmethylpiperazine, respectively, in place of ethyl-1-piperazine carboxylate.

Reference： [1]Patent: US5025012,1991,A

2
[ 132521-70-1 ]
[ 100-46-9 ]
[ 1108792-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	A suspension of <strong>[132521-70-1]6-(4-methyl-piperazin-1-yl)-nicotinic acid</strong> (200 mg) in DMF (2 ml) was treated under an argon atmosphere with diisopropylamine (0.50 ml), benzylamine (0.12 ml) and BOP (600 mg). The reaction mixture was stirred at r.t. overnight, then diluted with water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2?CH2Cl2/MeOH 9:1) to give N-benzyl-6-(4-methyl-piperazin-1-yl)-nicotinamide (120 mg) as off-white solid. MS (ISP): 311.3 ([M+H]+)

Reference： [1]Patent: US2009/36452,2009,A1 .Location in patent: Page/Page column 9

3
[ 132144-02-6 ]
[ 132521-70-1 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 6-(4-methyl-piperazin-1-yl)-nicotinic acid methyl ester (5.56 g) in MeOH/H2O 1:1 (100 ml) was cooled to 0 C. and treated with NaOH (1.9 g). The reaction mixture was stirred for 45 min at 0 C. and for 5 hrs at r.t., then neutralized with 1N HCl and concentrated. The crude product was used in the next reaction step without further purification.MS (ISP): 220.6 ([M-H])
	With ethanol; sodium hydroxide; In tetrahydrofuran; at 60℃; for 3.0h;	To a solution of methyl 6-(4-methylpiperazin-1-yl)nicotinate (650 mg, 2.76 mmol) in THF (10 ml) and EtOH(10 mE)was added 2M NaOH (1.5 mE, 3.04 mmol, 1.1 eq).The mixture was stirred at 60 C. for 3 h. When the reactionfinished, it was concentrated to remove solvent, HC1 (2 M)was added to adjust pH 5-7, concentrated to afford crudecompound as a white solid (1.0 g, crude, contained someNaC1).

Reference： [1]Patent: US2009/36452,2009,A1 .Location in patent: Page/Page column 8
[2]Patent: US2018/141923,2018,A1 .Location in patent: Paragraph 0666; 0669; 0670

4
[ 132521-70-1 ]
C₁₁H₁₄ClN₃O [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 629 - 634

5
[ 132521-70-1 ]
N-(6-(2,6-dichloro-3,5-dimethoxyphenyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)-6-(4-methylpiperazine-1-yl)nicotinamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 629 - 634

6
[ 132521-70-1 ]
[ 335255-35-1 ]
C₂₁H₂₃N₅O₂ [ No CAS ]

Reference： [1]Patent: US2018/141923,2018,A1

7
[ 132521-70-1 ]
[ 335255-35-1 ]
tert-butyl 4-(furan-3-yl)-2-(6-(4-methylpiperazin-1-yl)nicotinamido)phenylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20℃;	A mixture of 6-(4-methylpiperazin- 1 -yl)nicotinicacid (50 mg, 0.226 mmol), tert-butyl 2-amino-4-(thran-3- yl)phenylcarbamate (62 mg, 0.226 mmol) and EDCI (95 mg, 0.5 mmol) in pyridine (5 mE) was stirred at room temperature for overnight. The mixture was poured into water (20 mE) and extracted with EA to afford crude (170 mg, crude).

Reference： [1]Patent: US2018/141923,2018,A1 .Location in patent: Paragraph 0696; 0697; 0698

8
[ 132521-70-1 ]
[ 335255-53-3 ]
C₂₂H₂₄N₆O [ No CAS ]

Reference： [1]Patent: US2018/141923,2018,A1

9
[ 132521-70-1 ]
[ 335255-53-3 ]
C₂₇H₃₂N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20℃;	6-(4-methylpiperazin- 1 -yl)nicotinic acid (132 mg,0.6 mmol), tert-butyl 2-amino-4-(pyridin-4-yl) phenylcarbamate (172 mg, 0.6 mmol) and EDCI (346 mg, 1.8 mmol) were added into pyridine (5 ml). The mixture was stirred for overnight at room temperature. When the reaction finished, it was extracted by EA and washed by citric acid, NaHCO3 and saturated brine. Then the organic layer was concentrated to afford compound 2 (300 mg, crude).

Reference： [1]Patent: US2018/141923,2018,A1 .Location in patent: Paragraph 0370; 0371; 0372

10
[ 73781-91-6 ]
[ 132521-70-1 ]

Reference： [1]Patent: US2018/141923,2018,A1

11
[ 132521-70-1 ]
[ 335255-33-9 ]
tert-butyl 3-(6-(4-methylpiperazin-1-yl)nicotinamido)biphenyl-4-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
300 mg	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20℃;	A mixture of 6-(4-methylpiperazin- 1 -yl)nicotinicacid (150 mg, crude), tert-butyl 3-aminobiphenyl-4-ylcar-bamate (173 mg, 0.6 mmol) and EDCI (260 mg, 1.35 mmol)in pyridine (10 mE) was stirred at room temperature for overnight. The mixture was poured into water (20 mE), filtered to afford desired compound (300 mg, 89%) as a yellow solid.

Reference： [1]Patent: US2018/141923,2018,A1 .Location in patent: Paragraph 0666; 0671; 0672

12
[ 132521-70-1 ]
[ 335255-43-1 ]
[ 953434-82-7 ]

Yield	Reaction Conditions	Operation in experiment
280 mg	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20℃;	10678] A mixture of 6-(4-methylpiperazin- 1 -yl)nicotinicacid (150 mg, crude), tert-butyl 2-amino-4-(thiophen-2-yl)phenylcarbamate (174 mg, 0.6 mmol) and EDCI (260 mg,1.35 mmol) in pyridine (10 mE) was stirred at room temperature for overnight. The mixture was poured into water (20 mE), filtered to afford desired compound (280 mg, 84%) as a yellow solid.

Reference： [1]Patent: US2018/141923,2018,A1 .Location in patent: Paragraph 0676; 0677; 0678

13
[ 132521-70-1 ]
[ 335255-31-7 ]
C₂₁H₂₃N₅O₂ [ No CAS ]

Reference： [1]Patent: US2018/141923,2018,A1

14
[ 132521-70-1 ]
[ 335255-31-7 ]
tert-butyl 4-(furan-2-yl)-2-(6-(4-methylpiperazin-1-yl)nicotinamido)phenylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20℃;	A mixture of 6-(4-methylpiperazin- 1 -yl)nicotinic acid (100 mg, 0.45 mmol), tert-butyl 2-amino-4-(thran-2- yl)phenylcarbamate (124 mg, 0.45 mmol) and EDCI (191 mg, 1 mmol) in pyridine (5 mE) was stirred at room temperature for overnight. The mixture was poured into water (20 mE) and extracted with EA to afford crude (270 mg, crude).

Reference： [1]Patent: US2018/141923,2018,A1 .Location in patent: Paragraph 0691; 0692; 0693

15
[ 132521-70-1 ]
C₂₂H₂₃N₅O [ No CAS ]

Reference： [1]Patent: US2018/141923,2018,A1

16
[ 132521-70-1 ]
N-(2-amino-5-(thiophen-2-yl)phenyl)-6-(4-methylpiperazin-1-yl)nicotinamide [ No CAS ]

Reference： [1]Patent: US2018/141923,2018,A1

17
[ 132521-70-1 ]
C₂₁H₂₂N₆O [ No CAS ]

Reference： [1]Patent: US2018/141923,2018,A1

18
[ 132521-70-1 ]
C₂₂H₃₀BN₃O₄ [ No CAS ]
tert-butyl 4-(5-(2-(tert-butoxycarbonylamino)-5-(pyridin-3-yl)phenylcarbamoyl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20℃;	To a solution of 6-(4-(tert-butoxycarbonyl) piperazin-1-yl) nicotinic acid (123.7 mg, 0.40 mmol) and tertbutyl 2-amino-4-(pyridin-3-yl) phenylcarbamate (1, 3, 2-di- oxaborolane) (114.5 mg, 0.40 mmol) in Py (2.5 ml) was added EDCI (230 mg, 1.20 mmol). The mixture was stirred at room temperature for overnight. The residue was purified by preparative TLC (silica gel, GF254 10-40 u, 25x25 cm) with PE/EA (2:1) to afford a yellow solid (165 mg, 72%).

Reference： [1]Patent: US2018/141923,2018,A1 .Location in patent: Paragraph 0681; 0682; 0683

19
[ 109-01-3 ]
[ 132521-70-1 ]

Reference： [1]Patent: US2018/141923,2018,A1

Yield	Reaction Conditions	Operation in experiment
98.7%	With water; lithium hydroxide; In methanol; at 20℃; for 16.0h;	General procedure: To a solution of tert-butyl 4-(4-(ethoxycarbonyl)pyridin-2-yl)piperazine-1-carboxylate (XCIX) (10.7 g, 31.9 mmol) in MeOH (130 mL) and water (26 mL) was added 4 M aqueous lithium hydroxide (7.98 mL, 31.9 mmol). The reaction was stirred at room temperature for 16 h. The reaction was poured into water and neutralized with concentrated HCl (31.9 mL, 31.9 mmol) and extracted with EtOAc. The organic layer was dried over Na2SO4 and evaporated under high vacuum to produce 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)isonicotinic acid (C) as a white solid (8.79 g, 28.6 mmol, 89.7% yield) which was used without further purification. ESIMS found for C15H21N3O4 m/z 308.15 (M+H).

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Ghs Precautionary Statements

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Code	Phrase
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P321
P322
P330	Rinse mouth.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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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. 132521-70-1 ] {[proInfo.proName]}

Quality Control of [ 132521-70-1 ]

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[ 132521-70-1 ] Synthesis Path-Upstream 1~4

[ 132521-70-1 ] Synthesis Path-Downstream 1~20

Related Functional Groups of [ 132521-70-1 ]

Carboxylic Acids

Related Parent Nucleus of [ 132521-70-1 ]

Pyridines

Piperazines

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[ 132521-70-1 ]

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[ 132521-70-1 ]