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[ CAS No. 65169-64-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 65169-64-4
Chemical Structure| 65169-64-4
Chemical Structure| 65169-64-4
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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 :BARJEOMVLKJPRB-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :12404027
Synonyms :

Calculated chemistry of [ 65169-64-4 ]      Expand+

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 Ų

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 ]
YieldReaction ConditionsOperation 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.
  • 2
  • [ 25462-85-5 ]
  • [ 65169-64-4 ]
YieldReaction ConditionsOperation 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)
  • 3
  • [ 67-56-1 ]
  • [ 65169-64-4 ]
  • [ 1029128-50-4 ]
YieldReaction ConditionsOperation 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)
  • 4
  • [ 65169-64-4 ]
  • [ 75-36-5 ]
  • [ 1029128-50-4 ]
YieldReaction ConditionsOperation 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)
  • 5
  • [ 65169-64-4 ]
  • [ 1251527-64-6 ]
YieldReaction ConditionsOperation 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
  • 6
  • [ 65169-64-4 ]
  • C27H34ClN5O3*2ClH [ No CAS ]
YieldReaction ConditionsOperation 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
  • 7
  • [ 65169-64-4 ]
  • [ 1251528-23-0 ]
YieldReaction ConditionsOperation 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
  • 8
  • [ 65169-64-4 ]
  • [ 1372127-17-7 ]
YieldReaction ConditionsOperation 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
  • 9
  • [ 65169-64-4 ]
  • [ 124-40-3 ]
  • [ 1372127-42-8 ]
YieldReaction ConditionsOperation 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.
  • 10
  • [ 615-79-2 ]
  • [ 65169-64-4 ]
YieldReaction ConditionsOperation 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
  • 11
  • [ 89977-05-9 ]
  • [ 65169-64-4 ]
YieldReaction ConditionsOperation 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.
  • 12
  • [ 91558-58-6 ]
  • [ 65169-64-4 ]
YieldReaction ConditionsOperation 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
  • 13
  • [ 57508-48-2 ]
  • [ 615-79-2 ]
  • [ 65169-64-4 ]
YieldReaction ConditionsOperation 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;
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