72830-08-1|(3,4-Dimethoxypyridin-2-yl)methanol| Ambeed

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Quality Control of [ 72830-08-1 ] Purity: 98% SDS Specification

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Product Details of [ 72830-08-1 ]

CAS No. :	72830-08-1
Formula :	C₈H₁₁NO₃
M.W :	169.18
SMILES Code :	OCC1=NC=CC(OC)=C1OC
MDL No. :	MFCD06795941
InChI Key :	BKTHTLOKUUJKDF-UHFFFAOYSA-N
Pubchem ID :	10725809

Safety of [ 72830-08-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 72830-08-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.38
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	43.35
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	51.58 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.86
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.06
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.44
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.64
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.17
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.55

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.02
Solubility	16.0 mg/ml ; 0.0948 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.57
Solubility	45.3 mg/ml ; 0.268 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.1
Solubility	1.33 mg/ml ; 0.00787 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.37 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.97

Application In Synthesis of [ 72830-08-1 ]

* 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.

Downstream synthetic route of [ 72830-08-1 ]

[ 72830-08-1 ] Synthesis Path-Downstream 1~35

1
[ 72830-08-1 ]
[ 169905-10-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With thionyl chloride; In dichloromethane;	EXAMPLE I 3 Preparation of 3,4-dimethoxy-2-chloromethylpyridine 3,4-Dimethoxy-2-hydroxymethylpyridine (0.34 g, 0.002 mol) was dissolved in CH2 Cl2 (8 ml). SOCl2 (0.27 g, 0.00227 mol) in CH2 Cl2 (2 ml) was added under stirring at room temperature. After 10 min the mixture was neutralized with NaHCO3 (5 ml). The phases were separated, the CH2 Cl2 phase was washed with NaCl-solution, dried over Na2 SO4 and evaporated giving the desired product (0.61 g, 88%).
88%	With thionyl chloride; In dichloromethane;	Example I 1. Preparation of 3,4-dimethoxy-2-chloromethylpyridine. 3,4-Dimethoxy-2-hydroxymethylpyridine (0.34 g, 0.002 mol) was dissolved in CH2 Cl2 (8 ml). SOCl2 (0.27 g, 0.00227 mol) in CH2 Cl2 (2 ml) was added under stirring at room temperature. After 10 min the mixture was neutralized with NaHCO3 (5 ml). The phases were separated, the CH2 Cl2 phase was washed with NaCl-solution, dried over Na2 SO4 and evaporated giving the desired product (0.61 g, 88%).

References: [1]Patent: US4965269,1990,A .
[2]Patent: US5019584,1991,A .
[3]Journal of Medicinal Chemistry,1992,vol. 35,p. 438 - 450.

2
[ 72830-08-1 ]
[ 72830-09-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With bis(trichloromethyl) carbonate; Triphenylphosphine oxide; In toluene; at 20 - 60℃; for 4h;	Ph3PO (43.78 g, 157.5 mmol) was dissolved in toluene (100 mL) in a 500 mL three-necked flask and BTC(14.84 g, 50 mmol) was dissolved in toluene (60 mL) and placed in a 150 mL constant pressure dropping funnel. BTC was added dropwise at room temperature and the temperature was raised to 60 C after completion of the dropwise addition.After 2 hours of incubation, <strong>[72830-08-1]2-hydroxymethyl-3,4-dimethoxypyridine</strong> (25.35 g, 150 mmol) was dissolved in 75 mL of toluene and added at 40 C to precipitate a white solid. After incubation for 2 hours, The reaction was stopped and the white solid was obtained by suction filtration and dried to give 32.78 g of 2-chloromethyl-3,4-dimethoxypyridine hydrochloride, the product yield was 98%
93%	With thionyl chloride; In dichloromethane; at 0 - 20℃; for 2h;	Thionyl chloride (4 mL, 15.0 mmol) in dry dichloromethane(20 mL) was added dropwise to acooled (0-5 oC)stirred solution of hydroxymethyl)-3,4-dimethoxypyridine (6.76 g, 40.0 mmol) in dichloromethane (60 mL). The mixture wasallowed to warm up to 20 oC. After 2 h, the reaction mixture as concentratedin vacuo to a small volume. Addition of toluene afforded title product as a colorless solid (8.4 g, 93%). 1H NMR (CDCl3) d 8.56 (d, 1H, J = 6.63 Hz), 7.56 (d, 1H, J = 6.63 Hz), 5.06 (s, 2H), 4.23(s, 3H), 4.09 (s, 3H). m/z (ESI) 187.93 (M+ +1).
93.9%	With thionyl chloride; In dichloromethane; at 0 - 15℃; for 2h;	41 g of <strong>[72830-08-1]2-hydroxymethyl-3,4-dimethoxypyridine</strong> and 100 g of dichloromethane were added to the reaction flask, and the mixture was stirred and dissolved.30 g of thionyl chloride was slowly added dropwise at 0 to 5 C, and then slowly heated to 10 to 15 C for 2 h.Evaporate the dichloromethane under reduced pressure, add 90 g of absolute ethanol, and cool to 0 C.Drying to obtain 51 g of 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (yield 93.9%)

85%	With thionyl chloride; In dichloromethane; at 20℃;	A solution of (3,4-dimethoxypyridin-2-yl)methanol (1 g, 5.91 mmol) in CH2C12 (11.82 mL) was treated dropwise with thionyl chloride (1 mL, 13.70 mmol) with stirring at room temperature. The reaction mixture was stirred for 2 h, and then concentrated directly in vacuo. The resulting residue was washed with 3x 10 mL Et20, the resulting solids collected by filtration, and then dried under reduced pressure to afford the title compound as a white solid (1.12 g, 85%), which was used in the subsequent step without further purification.
	With thionyl chloride; In dichloromethane;	(a) 2-Chloromethyl-3,4-dimethoxy-pyridinium chloride 4.2 g (93% of theory) of the title compound are obtained as a colourless solid of m.p. 151-152 C. (decomp.) by the procedure described in Example A1a by reaction of 3.38 g of <strong>[72830-08-1]2-hydroxymethyl-3,4-dimethoxypyridine</strong> with 2 ml of thionyl chloride in 30 ml of methylene chloride, after a reaction time of 2.5 hours and after the type of working up described in Example A2a.
	With thionyl chloride; In dichloromethane;	(a) 2-Chloromethyl-3,4-dimethoxy-pyridinium chloride 4.2 g (93% of theory) of the title compound are obtained as a colorless solid of m.p. 151-152 C. (decomp.) by the procedure described in Example 32a by reacting 3.38 g of <strong>[72830-08-1]2-hydroxymethyl-3,4-dimethoxypyridine</strong> with 2 ml of thionyl chloride in 30 ml of methylene chloride, after a reaction time of 2.5 hours and after the type of working up described in Example 33a.
	With thionyl chloride; In toluene; at 3 - 40℃;	Add 9.22 kg of toluene,Add at room temperature<strong>[72830-08-1]2-hydroxymethyl-3,4-dimethoxypyridine</strong> 1.5kg,Cool down to 3 C ~ 10 C,Add 1.63 kg of thionyl chloride within 1 to 2 hours at 3 to 10 C.After the addition, the mixture was stirred at 5 to 10 C for 1 hour.Increase the temperature to 35 C ~ 40 C within 1 hour,Incubate at 35-40 C for 4 hours.After TLC detection, the temperature control is 35-40 C.Vacuum distilling thionyl chloride for 3 to 4 hours, adding 9 kg of toluene, and cooling to 20 to 25 C.Centrifugal filtration, 0.64 L of toluene washed filter cake, drained,Drying at 50-55 C for 6-8 hours,2-Chloromethyl-3,4-dimethoxypyridine hydrochloride (III) was obtained.

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4906 - 4916.
[2]Patent: CN107011252,2017,A .Location in patent: Paragraph 0079; 0080.
[3]Journal of Medicinal Chemistry,1992,vol. 35,p. 1049 - 1057.
[4]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2808 - 2811.
[5]Patent: CN104557692,2018,B .Location in patent: Paragraph 0038; 0039.
[6]Patent: WO2011/53559,2011,A1 .Location in patent: Page/Page column 31.
[7]Patent: US4686230,1987,A .
[8]Patent: US4758579,1988,A .
[9]Patent: CN109354587,2019,A .Location in patent: Paragraph 0168-0170.

3
[ 102625-99-0 ]
[ 72830-08-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In Petroleum ether;	(b) 2-Hydroxymethyl-3,4-dimethoxypyridine After adding 15 ml of 2N sodium hydroxide solution, 4.8 g of 2-acetoxymethyl-3,4-dimethoxypyridine are stirred vigorously at 80 C., whereupon a homogeneous solution forms from the initial two-phase mixture. After 2 hours, the solution is allowed to cool and is extracted five times with 30 ml of methylene chloride each time, the combined organic phases are washed twice with 5 ml of 0.3N sodium hydroxide solution each time, dried over potassium carbonate, filtered and concentrated and the distillation residue is stirred with petroleum ether. 3.6 g (96% of theory) of 2-hydroxymethyl-3,4-dimethoxypyridine are obtained as a colourless solid of m.p. 87-89 C.
	With sodium hydroxide; In Petroleum ether;	(b) 2-Hydroxymethyl-3,4-dimethoxypyridine After adding 15 ml of 2N sodium hydroxide solution, 4.8 g of 2-acetoxymethyl-3,4-dimethoxypyridine are stirred vigorously at 80 C., whereupon a homogeneous solution forms from the initial two-phase mixture. After 2 hours, the solution is allowed to cool and is extracted five times with 30 ml of methylene chloride each time, the combined organic phases are washed twice with 5 ml of 0.3N sodium hydroxide solution each time, dried over potassium carbonate, filtered and concentrated and the distillation residue is stirred with petroleum ether. 3.6 g (96% of theory) of 2-hydroxymethyl-3,4-dimethoxy-pyridine are obtained as a colorless solid of m.p. 87-89 C.

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1049 - 1057.
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 438 - 450.
[3]Journal of Medicinal Chemistry,1995,vol. 38,p. 4906 - 4916.
[4]Patent: US4686230,1987,A .
[5]Patent: US4758579,1988,A .

4
[ 118-71-8 ]
[ 72830-08-1 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4906 - 4916.
[2]Patent: CN104557692,2018,B .

5
[ 4780-14-7 ]
[ 72830-08-1 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4906 - 4916.

6
[ 76015-11-7 ]
[ 72830-08-1 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4906 - 4916.
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 1049 - 1057.
[3]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2808 - 2811.

7
[ 107512-34-5 ]
[ 72830-08-1 ]

8
[ 72830-08-1 ]
2-(3,4-Dimethoxy-pyridin-2-ylmethylsulfanyl)-5,6-difluoro-1H-benzoimidazole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4906 - 4916.

9
[ 72830-08-1 ]
2-(3,4-Dimethoxy-pyridin-2-ylmethanesulfinyl)-5,6-difluoro-1H-benzoimidazole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4906 - 4916.

10
[ 72830-07-0 ]
[ 72830-08-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With acetic anhydride; for 4h;Reflux;	45 g of 3,4-dimethoxy-2-methylpyridine oxynitride and 132 g of acetic anhydride were added to the reaction flask.Slowly raise the temperature to reflux, keep reflux for 4h, dilute the acetic anhydride and water 150g under reduced pressure, adjust the pH to 8~9.Add 20g sodium hydroxide to warm to 80 C, keep warm for 4h, cool down to 25 ~ 30 C,Extracted with dichloromethane 100g + 100g + 70g, and evaporated to dryness to give 41g of 2-hydroxymethyl-3,4-dimethoxypyridine (yield 91%)
76%		3,4-Dimethoxy-2-methylpyridineN-Oxide (9.6 g, 56.8 mmol) dissolved in aceticanhydride (50 mL) was heated at 90 oCfor 2 h. The dark oily residueobtained after evaporation of the volatiles in vacuo was agitated with 2N NaOH(40 mL) for 2 h at 80 oC. After cooling, the product wasextracted into dichloromethane (3 x 50 mL), dried over K2CO3, and concentrated in vacuo to ~10 mL. Addition of petroleum ether afforded the product as a colorless solid (7.20 g, 76%). 1H NMR (CDCl3) d 8.22 (d, 1H, J = 5.6 Hz), 6.82 (d, 1H, J= 5.6 Hz), 4.76 (s, 2H), 3.93 (s, 3H), 3.85 (s, 3H). m/z (ESI) 192.15 (M+ +Na).

References: [1]Patent: CN104557692,2018,B .Location in patent: Paragraph 0036; 0037.
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2808 - 2811.
[3]Journal of Medicinal Chemistry,1995,vol. 38,p. 4906 - 4916.
[4]Journal of Medicinal Chemistry,1992,vol. 35,p. 1049 - 1057.
[5]Journal of Medicinal Chemistry,1992,vol. 35,p. 438 - 450.

11
[ 107512-35-6 ]
[ 72830-08-1 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4906 - 4916.
[2]Patent: CN104557692,2018,B .

12
[ 15931-25-6 ]
[ 72830-08-1 ]