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[ CAS No. 851759-19-8 ] {[proInfo.proName]}

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Chemical Structure| 851759-19-8
Chemical Structure| 851759-19-8
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Product Details of [ 851759-19-8 ]

CAS No. :851759-19-8 MDL No. :MFCD14155903
Formula : C8H8ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BBXGEZRYRMLKTJ-UHFFFAOYSA-N
M.W :185.61 Pubchem ID :59650775
Synonyms :

Calculated chemistry of [ 851759-19-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.49
TPSA : 39.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 2.07
Log Po/w (WLOGP) : 1.83
Log Po/w (MLOGP) : 1.25
Log Po/w (SILICOS-IT) : 2.29
Consensus Log Po/w : 1.93

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.53
Solubility : 0.544 mg/ml ; 0.00293 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.558 mg/ml ; 0.003 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.1
Solubility : 0.146 mg/ml ; 0.000785 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.76

Safety of [ 851759-19-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 851759-19-8 ]

* 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 [ 851759-19-8 ]

[ 851759-19-8 ] Synthesis Path-Downstream   1~55

  • 1
  • [ 1033809-42-5 ]
  • [ 851759-19-8 ]
  • [ 177785-14-7 ]
YieldReaction ConditionsOperation in experiment
Step 2. Methyl 6-cMoro~2-memvlpvridme-3-carbrhoxylate and methyl 2-(chloromethyl)pyriduie-3 -carboxylateMethyl 2-methylpyridine-3 -carboxylate 1-oxide (2.93 g, 17.53 mmol) was stirred in refluxing POCl3 (17 mL, 182 mmol) for 3 hours. Room temperature was attained and the reaction mixture poured into ice- water. The resulting dark solution was neutralised with solid Na2CO3 and the mixture was extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel chromatography (2-30% EtOAc/hexanes) gave methyl 6-chloro-2- methylrhoyridine-3-carboxylate as a pale yellow oil (A) and methyl 2-(chloromethyl)pyridine-3- carboxylate (B) as an orange oil.A - 1H NMR (600 MHz, CDCl3): delta 8.13 (d, J- 8.4 Hz, 1 H), 7.21 (d, J= 8.4 Hz, 1 H), 3.89 (s, 3H), 2.79 (s, 3 H).B - 1HNMR (OOO MHz, CDCl3): delta 8.70 (dd, J- 5.4 and 1.8 Hz, 1 H), 8.26 (dd, J= 7.8 and 1.8Hz, 1 H)5 7.34 (dd, J= 7.8 and 5.4 Hz5 1 H), 3.87 (s, 3 H), 2.79 (s, 3 H).
  • 2
  • [ 1104383-06-3 ]
  • [ 851759-19-8 ]
  • tert-butyl 4-(5-methoxycarbonyl-6-methyl-2-pyridyl)-2,2-dimethyl-3-oxopiperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% To a solution of tert-butyl 2,2-dimethyl-3-oxo-piperazine-1-carboxylate (1.60 g, 7.01 mmol) in DMF (10 mL) is added 60% NaH/mineral (280 mg, 7.00 mmol). The mixture is stirred at rt for 20 mm, till the bubbling subsided. Then to it are added TBAI (70 mg, 0.19 mmol) and tertbutyl 2,2-dimethyl-3-oxo-piperazine-1-carboxylate (1.6 g, 7.1 mmol). The mixture is stirred at rt for lh under nitrogen, LC-MS of the crude shows a littlew conversion. Then the temperature is raised to 60C, stirred for 3h. After cooling to rt, the mixture is neutralized with formic acid, diluted with Et0Ac (80 mL), washed with water and brine consecutively, dried over sodium sulfate, filtered. The filtrate is concentrated to dryness under reduced pressure and the residue is purified on Biotage SNAP 50g silica gel cartridge eluting with Et0Ac/hexanes 0-30% in 2OCV to obtain tert-butyl 4-(5-methoxycarbonyl-6-methyl-2-pyridyl )-2,2-dimethyl-3-oxo-piperazine-1- carboxylate (755 mg, 37%) as a yellowish solid. LC-MS: 378.77 M(+H+), calc. 378.2028. RT: 1.9 mm using Method C.
  • 3
  • [ 1104383-06-3 ]
  • [ 851759-19-8 ]
  • methyl 6-(3,3-dimethyl-2-oxopiperazin-1-yl)-2-methylpyridine-3-carboxylate dihydrochloride [ No CAS ]
  • 4
  • [ 65719-09-7 ]
  • [ 851759-19-8 ]
  • 5
  • [ 851759-19-8 ]
  • [ 75-16-1 ]
  • [ 1093880-32-0 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; diethyl ether; at 0 - 20℃; for 3h;Inert atmosphere; Step 2: Preparation of 2-(6-chloro-2-methylpyridin-3-yl)propan-2-ol Methyl 6-chloro-2-methylnicotinate (900 mg, 4.85 mmol) was dissolved in dry THF (24 mL) in a 100 mL RBF under N2. The solution was cooled to 0 C. and MeMgBr (3.0 M in Et2O) (4.85 mL, 14.55 mmol) was added dropwise. The reaction warmed to RT of its own accord and continued stirring for 3 h. The reaction was cooled to 0 C. and quenched slowly with 1M HCl aq. (1 mL) followed by water (20 mL). The mixture was diluted with EtOAc (30 mL) and stirred for 10 min. The layers were separated and the aqueous layer was extracted with EtOAc (3*20 mL), and the combined organic layers were dried over sodium sulfate, filtered and concentrated to afford a yellow oil. This material was used in the subsequent step without further purification. LC-MS Rt=1.26 min (Condition A), MS (M+1)=182.2.
  • 6
  • [ 67-56-1 ]
  • [ 137129-98-7 ]
  • [ 851759-19-8 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; at 20℃; Step 1: Preparation of methyl 6-chloro-2-methylnicotinate 6-Chloro-2-methylnicotinic acid (1.0 g, 5.83 mmol) was dissolved in MeOH (30 mL) in a 100 mL RBF. SOCl2 (2.13 mL, 29.1 mmol) was added and the reaction was stirred at RT overnight. The reaction was cooled to 0 C. and quenched with saturated aqueous NaHCO3, then the aqueous layer was extracted with EtOAc (3*100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. This material was used in the subsequent step without further purification.
  • 7
  • [ 1033809-42-5 ]
  • [ 851759-19-8 ]
YieldReaction ConditionsOperation in experiment
24% With trichlorophosphate; for 3h;Reflux; 3-(Methoxycarbonyl)-2-methylpyridine 1-oxide (9.5 g, 56.14 mmol, 1.0 eq) was added to phosphorus oxychloride (35 mL).Heat to reflux for 3 hours.LC-MS detected the reaction was complete and the system was cooled to room temperature.The reaction solution was directly concentrated under reduced pressure.Remove most of the solvent and pour into ice water (100 mL).Adjust the pH to 7-8 with NaOH and extract with EA (100 mL×3).Combine the organic phases, dry and concentrate.The crude product was purified by silica gel column chromatography (200-300 mesh silica gel, EA/PE = 0 to 5%)The product was obtained as a white solid (2.5 g, yield: 24%).
  • 8
  • [ 851759-19-8 ]
  • methyl 2-(bromomethyl)-6-methoxynicotinate [ No CAS ]
  • 9
  • [ 851759-19-8 ]
  • 6-cyclopropyl-2-methoxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one [ No CAS ]
  • 10
  • [ 851759-19-8 ]
  • 6-cyclopropyl-2-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one [ No CAS ]
  • 11
  • [ 851759-19-8 ]
  • (E)-(2-(((6-cyclopropyl-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-2-yl)oxy)methyl)-3-fluoroallyl)carbamic acid tert-butyl ester [ No CAS ]
  • 12
  • [ 851759-19-8 ]
  • C2HF3O2*C14H16FN3O2 [ No CAS ]
  • 13
  • [ 851759-19-8 ]
  • C19H24FN3O4 [ No CAS ]
  • 14
  • [ 851759-19-8 ]
  • C2HF3O2*C14H16FN3O2 [ No CAS ]
  • 15
  • [ 851759-19-8 ]
  • [ 124-41-4 ]
  • 6-methoxy-2-methylnicotinate methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.7% In methanol; for 12h;Reflux; The intermediate <strong>[851759-19-8]6-chloro-2-methylnicotinate methyl ester</strong> (1.9 g, 10.24 mmol, 1.0 eq)Add sodium methoxide (1.1 g, 20.48 mmol, 2.0 eq) to methanol (35 mL).The reaction was heated to reflux for 12 hours.After the reaction was completed by LC-MS, the system was cooled to room temperature, and the reaction mixture was concentrated under reduced pressure.(100-200 mesh silica gel, EA/PE=0~2%)A colorless oily product (1.4 g, yield: 73.7%) was obtained.
  • 16
  • [ 14205-39-1 ]
  • [ 851759-19-8 ]
  • 17
  • [ 223788-08-7 ]
  • [ 851759-19-8 ]
YieldReaction ConditionsOperation in experiment
98.7% With trichlorophosphate; at 100℃; for 4h; Add 500mL reaction flasks one by one6-hydroxy-2-methylnicotinic acid methyl ester (140g, 0.84mol),300 mL of phosphorus oxychloride,The reaction was heated to 100 C for 4 hours.Concentrated under reduced pressure,The residue was slowly poured into 1000 mL of ice water,A large amount of gray-black solid precipitated,Stir for 1 hour,Suction filtration,The cake was air-dried at room temperature.153 g of methyl 6-chloro-2-methylnicotinate was obtained, 98.7%.
  • 18
  • [ 851759-19-8 ]
  • 2-((2-(3-chlorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
  • 19
  • [ 851759-19-8 ]
  • 2-((2-(3-chlorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
  • 20
  • [ 851759-19-8 ]
  • 2-((2-(4-chlorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
  • 21
  • [ 851759-19-8 ]
  • 2-((2-(4-chlorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridin-6-yl)formylamino)acetic acid [ No CAS ]
  • 22
  • [ 851759-19-8 ]
  • 2-((2-(4-fluorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
  • 23
  • [ 851759-19-8 ]
  • 2-((2-(4-fluorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
  • 24
  • [ 851759-19-8 ]
  • 2-((2-(4-hydroxyphenoxy)-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
  • 25
  • [ 851759-19-8 ]
  • 2-((2-ethoxy-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
  • 26
  • [ 851759-19-8 ]
  • (2-((2-phenoxy-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formylamino)acetoxy)methyl pivalate [ No CAS ]
  • 27
  • [ 851759-19-8 ]
  • 2-((2-phenoxy-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
  • 28
  • [ 851759-19-8 ]
  • methyl 2-(bromomethyl)-6-chloronicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80.7% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 80℃; for 8h; In a 1000mL reaction flask,Add methyl 2-methyl-6-chloronicotinate (153 g, 0.82 mol), N-bromosuccinimide (161 g, 0.90 mol),Benzoyl peroxide (40g, 0.16mol),750mL of carbon tetrachloride,The reaction was heated to 80 C for 8 hours.Concentrated under reduced pressure,Add 100 mL of petroleum ether to the residue,Light yellow solid precipitated,Stir for 1 hour,Suction filtration,Vacuum dry constant weight,176 g of methyl 2-bromomethyl-6-chloronicotinate was obtained, 80.7%.
  • 29
  • [ 851759-19-8 ]
  • ethyl 2-chloro-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
  • 30
  • [ 851759-19-8 ]
  • ethyl 2-phenoxy-5-hydroxy-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 31
  • [ 851759-19-8 ]
  • 2-((2-(4-methoxyphenoxy)-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
  • 32
  • [ 851759-19-8 ]
  • ethyl 2-phenoxy-5-hydroxy-8-chloro-1,7-naphthyridine-6carboxylate [ No CAS ]
  • 33
  • [ 851759-19-8 ]
  • ethyl 2-(4-methoxyphenoxy)-5-hydroxy-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 34
  • [ 851759-19-8 ]
  • ethyl 2-(4-methoxyphenoxy)-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 35
  • [ 851759-19-8 ]
  • ethyl 2-phenoxy-5-hydroxy-8-bromo-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 36
  • [ 851759-19-8 ]
  • ethyl 2,8-dichloro-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
  • 37
  • [ 851759-19-8 ]
  • ethyl 2-(2-chlorophenoxy)-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
  • 38
  • [ 851759-19-8 ]
  • ethyl 2-(2-chlorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 39
  • [ 851759-19-8 ]
  • ethyl 2-(2-chlorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 40
  • [ 851759-19-8 ]
  • 2-((2-phenoxy-5-hydroxy-8-bromo-1,7-naphthyridin-6-yl)formylamino)acetic acid [ No CAS ]
  • 41
  • [ 851759-19-8 ]
  • ethyl 2-(4-chlorophenoxy)-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
  • 42
  • [ 851759-19-8 ]
  • ethyl 2-(3-chlorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 43
  • [ 851759-19-8 ]
  • ethyl 2-(3-chlorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 44
  • [ 851759-19-8 ]
  • ethyl 2-(3-chlorophenoxy)-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
  • 45
  • [ 851759-19-8 ]
  • ethyl 2-(4-chlorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 46
  • [ 851759-19-8 ]
  • ethyl 2-(4-fluorophenoxy)-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
  • 47
  • [ 851759-19-8 ]
  • ethyl 2-(4-fluorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 48
  • [ 851759-19-8 ]
  • 2-((2,8-dichloro-5-hydroxy-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
  • 49
  • [ 851759-19-8 ]
  • ethyl 2-(4-fluorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 50
  • [ 851759-19-8 ]
  • ethyl 2-(4-hydroxyphenoxy)-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 51
  • [ 851759-19-8 ]
  • ethyl 2-ethoxy-5-hydroxy-1,7-naphthyridin-6-carboxylate [ No CAS ]
  • 52
  • [ 851759-19-8 ]
  • ethyl 2-ethoxy-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 53
  • [ 851759-19-8 ]
  • 2-((2-(2-chlorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
  • 54
  • [ 851759-19-8 ]
  • ethyl 2-(4-chlorophenoxy)-5-hydroxy-8-chloro-1,7-naphthyridine-6-carboxylate [ No CAS ]
  • 55
  • [ 851759-19-8 ]
  • 2-((2-(2-chlorophenoxy)-5-hydroxy-8-bromo-1,7-naphthyridin-6-yl)formamido)acetic acid [ No CAS ]
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