[ CAS No. 65169-64-4 ]

Name: 65169-64-4|2-Amino-6-methylisonicotinic acid|95%
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SKU: A247011
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Quality Control of [ 65169-64-4 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 65169-64-4 ]

CAS No. :	65169-64-4	MDL No. :	MFCD13188664
Formula :	C₇H₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	152.15 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 65169-64-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	40.57
TPSA :	76.21 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.9
Log Po/w (XLOGP3) :	0.43
Log Po/w (WLOGP) :	0.68
Log Po/w (MLOGP) :	-0.96
Log Po/w (SILICOS-IT) :	0.46
Consensus Log Po/w :	0.3

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.39
Solubility :	6.17 mg/ml ; 0.0406 mol/l
Class :	Very soluble
Log S (Ali) :	-1.6
Solubility :	3.84 mg/ml ; 0.0252 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.41
Solubility :	5.92 mg/ml ; 0.0389 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 65169-64-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 65169-64-4 ]

* 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 [ 65169-64-4 ]

[ 65169-64-4 ] Synthesis Path-Downstream 1~13

1
[ 65169-64-4 ]
[ 2834-84-6 ]
3-amino-5-(2-amino-6-methyl-pyridin-4-yl)-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
200 mg. (18%)	In methanol; ethyl acetate	XXX EXAMPLE XXX EXAMPLE XXX An intimate mixture consisting of 913 mg. (0.006 mole) of 2-amino-6-methylisonicotinic acid and 1.11 g. (0.0045 mole) of aminoguanidine sulfate was placed in a suitable reaction flask and heated at 205° C. for a period of 16 hours while under a nitrogen atmosphere. Upon completion of the reaction, the contents of the flask were cooled to room temperature (~25° C.) and the spent reaction mixture was subsequently treated with 50 ml. of saturated aqueous sodium bicarbonate solution. The basified aqueous mixture so obtained was next filtered and the resulting filtrate thereafter concentrated in vacuo to afford a semi-solid residue. Trituration of the latter material with hot methanol, followed by filtration, then gave an oil in the form of the filtrate. The latter oil was then concentrated in vacuo and subsequently chromatographed over 40 g. of silica gel using 5% methanol in ethyl acetate as the eluant to ultimately afford 200 mg. (18%) of pure 3-amino-5-(2-amino-6-methyl-4-pyridyl)-1,2,4-triazole in the form of a yellow solid, m.p. 98°-106° C.

Reference： [1]Current Patent Assignee: PFIZER INC - US4276297, 1981, A

2
[ 25462-85-5 ]
[ 65169-64-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium sulfide; ammonia; copper(II) sulfate; In water; at 155℃;Autoclave;	2-chloro-6-methylnicotinic acid (9 g), of aq ammonia (44 ml), of Cu(II)SO4 (0.9 g) and of sodium sulphide (0.32 g) were added to an autoclave and heated to 155 C. overnight. The crude product was suspended in water to yield product 115 (3.6 g). The filtrate was concentrated and again suspended in water to yield a further 1.9 g of product 115. HPLC: Rt=0.37 min (method D)
	With sodium sulfide; ammonia; copper(II) sulfate; at 155℃;	Step a: <strong>[25462-85-5]2-chloro-6-methylisonicotinic acid</strong> (9 g), of aq ammonia (44 ml), ofCu(ll)S04 (0.9 g) and of sodium sulphide (0.32 g) are added to an autoclave and heated to 155C overnight. The crude product is suspended in water to yield 2- amino-6-methylisonicotinic acid (3.6 g). HPLC: Rt = 0.37 min (method D)
	With ammonia;sodium sulfide; copper(II) sulfate; In water; at 155℃;autoclave;	<strong>[25462-85-5]2-chloro-6-methylisonicotinic acid</strong> (9 g), of aq ammonia (44 ml), of Cu(II)SO4 (0.9 g) and of sodium sulphide (0.32 g) are added to an autoclave and heated to 155 C. overnight. The crude product is suspended in water to yield 2-amino-6-methylisonicotinic acid (3.6 g). HPLC: Rt=0.37 min (method D)

Reference： [1]Patent: US2010/261687,2010,A1 .Location in patent: Page/Page column 48
[2]Patent: WO2012/45803,2012,A1 .Location in patent: Page/Page column 27
[3]Patent: US2012/264729,2012,A1 .Location in patent: Page/Page column 9

3
[ 67-56-1 ]
[ 65169-64-4 ]
[ 1029128-50-4 ]

Yield	Reaction Conditions	Operation in experiment
51.2%	With sulfuric acid at 20℃; for 6h; Reflux;	3 Example 3: Preparation of 2-amino-6-methyl-isonicotinic acid methyl ester (Compound 6) To a slurry of 340 mg of 2-amino-6-methyl-isonicotinic acid in 1.6 mL of methanol is added 170 mg of conc. sulfuric acid slowly at room temperature. The reaction mixture is heated to reflux for 6 h and then cooled to room temperature. Methanol is removed by evaporator at 50°C. A total of 1.6 mL of water is added and the mixture is adjusted to pH = 6.5-7.0. The product is precipitated as solid. It is collected by filtration and washed with 1 mL water twice. A total of 190 mg (yield 51.2%) of the desired product is obtained after being dried at 60°C in vacuum oven. ‘H NMR (400 MHz, DMSO-d6): 8 6.78 (d, 2H), 6.24 (s, 2H), 3.84 (s, 3H), 2.31 (s, 3H); ‘3C NMR (100 MHz, DMSO-d6): 8 165.06, 160.00, 157.32, 138.21, 109.33, 104.49, 52.20, 23.74; MS (m/z+1): 167.1.
	With acetyl chloride at 50℃;	S.2.2.2 To 50 ml of MeOH was added dropwise acetylchloride (3 ml) at rt. After 15 min, intermediate 115 (2.3 g) was added and the mixture was stirred overnight at 50° C. After concentrating the solution, the resulting residue was suspended in acetone and then filtered and dried at 50° C. in vacuum, to yield product 116 (4.1 g).HPLC: Rt=0.91 min (method D)
	With acetyl chloride at 50℃;	b To 50 ml of MeOH is added drop wise acetyl chloride (3 ml) at room temperature. After 15 min, 2-amino-6-methylisonicotinic acid (2.3 g) is added and the mixture is stirred overnight at 50° C. After concentrating the solution, the resulting residue is suspended in acetone and then filtered and dried at 50° C. in vacuum, to yield 2-amino-6-methylisonicotinic acid methyl ester (4.1 g). HPLC: Rt=0.91 min (method D)

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2017/1670, 2017, A1 Location in patent: Page/Page column 9; 25
[2]Current Patent Assignee: GRIFOLS SA - US2010/261687, 2010, A1 Location in patent: Page/Page column 48
[3]Current Patent Assignee: GRIFOLS SA - US2012/264729, 2012, A1 Location in patent: Page/Page column 9

4
[ 65169-64-4 ]
[ 75-36-5 ]
[ 1029128-50-4 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol at 50℃;	2.b Step b: To 50 ml of MeOH is added drop wise acetyl chloride (3 ml) at room temperature. After 15 min, 2-amino-6-methylisonicotinic acid (2.3 g) is added and the mixture is stirred overnight at 50°C. After concentrating the solution, the resulting residue is suspended in acetone and then filtered and dried at 50°C in vacuum, to yield 2-amino-6-methylisonicotinic acid methyl ester (4.1 g). HPLC: Rt = 0.91 min (method D)

Reference： [1]Current Patent Assignee: GRIFOLS SA - WO2012/45803, 2012, A1 Location in patent: Page/Page column 27

5
[ 65169-64-4 ]
[ 1251527-64-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: methanol / 50 °C 2: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate; tetrahydrofuran / 0.5 h / 50 °C
	Multi-step reaction with 2 steps 1: acetyl chloride / 50 °C 2: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate; tetrahydrofuran / 50 °C

Reference： [1]Current Patent Assignee: GRIFOLS SA - WO2012/45803, 2012, A1
[2]Current Patent Assignee: GRIFOLS SA - US2012/264729, 2012, A1

6
[ 65169-64-4 ]
C₂₇H₃₄ClN₅O₃*2ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: methanol / 50 °C 2.1: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate; tetrahydrofuran / 0.5 h / 50 °C 3.1: sodium hydroxide / isopropyl alcohol; water / 1 h / 55 °C 3.2: 50 °C 3.3: 1.5 h / 50 °C

Reference： [1]Current Patent Assignee: GRIFOLS SA - WO2012/45803, 2012, A1

7
[ 65169-64-4 ]
[ 1251528-23-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: acetyl chloride / 50 °C 2.1: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate; tetrahydrofuran / 50 °C 3.1: sodium hydroxide; water / isopropyl alcohol / 1 h / 55 °C 3.2: 1.5 h / 50 °C

Reference： [1]Current Patent Assignee: GRIFOLS SA - US2012/264729, 2012, A1

8
[ 65169-64-4 ]
[ 1372127-17-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: acetyl chloride / 50 °C 2.1: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate; tetrahydrofuran / 50 °C 3.1: sodium hydroxide; water / isopropyl alcohol / 1 h / 55 °C 3.2: 1.5 h / 50 °C 4.1: ethanol; water / 70 °C

Reference： [1]Current Patent Assignee: GRIFOLS SA - US2012/264729, 2012, A1

9
[ 65169-64-4 ]
[ 124-40-3 ]
[ 1372127-42-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 2-amino-6-methylisonicotinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 5℃; for 1h; Stage #2: dimethyl amine In dichloromethane; water for 1h;	4 Example 4: Preparation of 2-amino-6,N,N-trimethyl-isonicotinamide (Compound 7) To a slurry of 110 mg of 2-amino-6-methyl-isonicotinic acid in 1.1 mL of dichloromethane is added 0.01 mL of DMF. The mixture is cooled to 0-5 °C and 122 mg of oxalyl chloride is added slowly. The reaction mixture is stirred at 0-5 °C for 1 h, and then 400 mg of 40% dimethylamine aq. solution is added dropwise. The mixture is stirred for 1 h, followed by addition of 50 mg of NaCI. The organic phase is separated. The aqueous phase is extracted by 0.4 mL dichloromethane twice. The combined organic phase is washed with 0.3 mL of 25% sodium chloride aq. solution. It is then concentrated by evaporator and 1 mL of toluene is added. The resulting solid is collected by filtration and washed with 1 mL of toluene. A total of 94 mg (yield 72.0%) of the desired product is obtained after being dried at 60°C in vacuum oven. ‘H NMR (400 MHz, DMSO-d6): 8 6.28 (s, 1H), 6.14 (s, 1H), 6.06 (s, 2H), 2.93 (s, 3H), 2.86 (s, 3H), 2.24 (s, 3H); ‘3C NMR (100 MHz, DMSO-d6): 8 168.97, 159.31, 156.45, 145.57, 107.95, 101.95, 34.18, 32.76; MS (m/z+1): 180.2.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2017/1670, 2017, A1 Location in patent: Page/Page column 10; 26

10
[ 615-79-2 ]
[ 65169-64-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium ethanolate / ethanol / 2 h / 20 °C / Reflux 1.2: 1 h / Reflux 2.1: lithium chloride hydrate; sulfuric acid / 1-methyl-pyrrolidin-2-one / 48 h / 130 °C
	Multi-step reaction with 3 steps 1: sodium ethanolate / ethanol / 2 h / Reflux; Inert atmosphere 2: sodium hydroxide; water / water / 1 h / Reflux; Inert atmosphere 3: lithium chloride hydrate; sulfuric acid / 1-methyl-pyrrolidin-2-one / 48 h / 130 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2017/1670, 2017, A1
[2]Deng, Daniel Da; Dong, Weitong; Fu, Yan; Jin, Xiangle; Xing, Lidong; Yan, Jun [Journal of Organic Chemistry, 2022, vol. 87, # 2, p. 1541 - 1544]

11
[ 89977-05-9 ]
[ 65169-64-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With lithium chloride hydrate; sulfuric acid In 1-methyl-pyrrolidin-2-one at 130℃; for 48h; Inert atmosphere;
83.7%	With lithium chloride hydrate; sulfuric acid In 1-methyl-pyrrolidin-2-one at 130℃; for 48h;	2 Example 2: Preparation of 2-amino-6-methyl-isonicotinic acid (Compound 5) To a slurry of 154 mg of 2-amino-6-methyl-pyridine-3,4-dicarboxylic acid in 0.65 mL of NMP are added 50 mg of LiC[H20 and 190 mg of conc. H2S04. The reaction mixture is heated to 130°C and stirred for 48 h. It is then cooled to 20-30°C, and 1.6 mL of water is added. The resulting reaction mixture is adjusted to pH = 6-7. The product is precipitated as solid. It is collected by filtration and washed with 1 mL water twice. A total of 100 mg (yield 83.7%) of the desired product is obtained after being dried at 60°C in vacuum oven. ‘H NMR (400 MHz, D20 with NaOD): 8 6.69 (s, 1H), 6.61 (s, 1H), 2.13 (s, 3H); ‘3C NMR: (100 MHz, D20 with NaOD) 8 177.78, 158.62, 156.05, 147.21, 112.60, 106.08, 22.66; MS (m/z+1): 153.1.

Reference： [1]Deng, Daniel Da; Dong, Weitong; Fu, Yan; Jin, Xiangle; Xing, Lidong; Yan, Jun [Journal of Organic Chemistry, 2022, vol. 87, # 2, p. 1541 - 1544]
[2]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2017/1670, 2017, A1 Location in patent: Page/Page column 9; 10; 25

12
[ 91558-58-6 ]
[ 65169-64-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide; water / water / 1 h / Reflux; Inert atmosphere 2: lithium chloride hydrate; sulfuric acid / 1-methyl-pyrrolidin-2-one / 48 h / 130 °C / Inert atmosphere

Reference： [1]Deng, Daniel Da; Dong, Weitong; Fu, Yan; Jin, Xiangle; Xing, Lidong; Yan, Jun [Journal of Organic Chemistry, 2022, vol. 87, # 2, p. 1541 - 1544]

13
[ 57508-48-2 ]
[ 615-79-2 ]
[ 65169-64-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: carbethoxyacetamidine hydrochloride With sodium hydroxide In water at 10 - 30℃; for 3h; Inert atmosphere; Stage #2: ethyl 2,4-diketopentanoate In ethanol; water at 0 - 10℃; Inert atmosphere; Further stages;

Reference： [1]Deng, Daniel Da; Dong, Weitong; Fu, Yan; Jin, Xiangle; Xing, Lidong; Yan, Jun [Journal of Organic Chemistry, 2022, vol. 87, # 2, p. 1541 - 1544]

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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. 65169-64-4 ]

Quality Control of [ 65169-64-4 ]

Related Doc. of [ 65169-64-4 ]

Product Details of [ 65169-64-4 ]

Calculated chemistry of of [ 65169-64-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 65169-64-4 ]

Application In Synthesis of [ 65169-64-4 ]

[ 65169-64-4 ] Synthesis Path-Downstream 1~13

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