[ CAS No. 851759-19-8 ]

Name: 851759-19-8|Methyl 6-chloro-2-methylnicotinate|97%
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SKU: A781055
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Quality Control of [ 851759-19-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 851759-19-8 ]

SDS Specification

Alternatived Products of [ 851759-19-8 ]

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 g/mol	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 Å²

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 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Patent: WO2009/155156,2009,A1 .Location in patent: Page/Page column 52-53

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 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Patent: WO2018/57588,2018,A1 .Location in patent: Paragraph 0241; 0280

3
[ 1104383-06-3 ]
[ 851759-19-8 ]
methyl 6-(3,3-dimethyl-2-oxopiperazin-1-yl)-2-methylpyridine-3-carboxylate dihydrochloride [ No CAS ]

Reference： [1]Patent: WO2018/57588,2018,A1

4
[ 65719-09-7 ]
[ 851759-19-8 ]

Reference： [1]Patent: WO2009/155156,2009,A1
[2]Patent: CN109810041,2019,A

5
[ 851759-19-8 ]
[ 75-16-1 ]
[ 1093880-32-0 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Patent: US2019/77773,2019,A1 .Location in patent: Paragraph 1233

6
[ 67-56-1 ]
[ 137129-98-7 ]
[ 851759-19-8 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Patent: US2019/77773,2019,A1 .Location in patent: Paragraph 1232

7
[ 1033809-42-5 ]
[ 851759-19-8 ]

Yield	Reaction Conditions	Operation 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%).

Reference： [1]Patent: CN109810041,2019,A .Location in patent: Paragraph 0373; 0380-0382

8
[ 851759-19-8 ]
methyl 2-(bromomethyl)-6-methoxynicotinate [ No CAS ]

Reference： [1]Patent: CN109810041,2019,A

9
[ 851759-19-8 ]
6-cyclopropyl-2-methoxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one [ No CAS ]

Reference： [1]Patent: CN109810041,2019,A

10
[ 851759-19-8 ]
6-cyclopropyl-2-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one [ No CAS ]

Reference： [1]Patent: CN109810041,2019,A

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 ]

Reference： [1]Patent: CN109810041,2019,A

12
[ 851759-19-8 ]
C₂HF₃O₂*C₁₄H₁₆FN₃O₂ [ No CAS ]

Reference： [1]Patent: CN109810041,2019,A

13
[ 851759-19-8 ]
C₁₉H₂₄FN₃O₄ [ No CAS ]

Reference： [1]Patent: CN109810041,2019,A

14
[ 851759-19-8 ]
C₂HF₃O₂*C₁₄H₁₆FN₃O₂ [ No CAS ]

Reference： [1]Patent: CN109810041,2019,A

15
[ 851759-19-8 ]
[ 124-41-4 ]
6-methoxy-2-methylnicotinate methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Patent: CN109810041,2019,A .Location in patent: Paragraph 0373; 0383-0385

16
[ 14205-39-1 ]
[ 851759-19-8 ]