1461602-59-4|3-(Methylamino)isonicotinic Acid| Ambeed

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Quality Control of [ 1461602-59-4 ] Purity: 97% SDS Specification

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Product Details of [ 1461602-59-4 ]

CAS No. :	1461602-59-4
Formula :	C₇H₈N₂O₂
M.W :	152.15
SMILES Code :	O=C(O)C1=CC=NC=C1NC
MDL No. :	MFCD24160213
InChI Key :	JHSWDRAGEBOUER-UHFFFAOYSA-N
Pubchem ID :	81750543

Safety of [ 1461602-59-4 ]

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 [ 1461602-59-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	40.5
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	62.22 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.02
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	0.91
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.63
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.	-1.36
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	0.39
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.32

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.63
Solubility	3.58 mg/ml ; 0.0235 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.	-1.8
Solubility	2.4 mg/ml ; 0.0158 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	-1.82
Solubility	2.3 mg/ml ; 0.0151 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.	-6.58 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.	0.56

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)	1.49

Application In Synthesis of [ 1461602-59-4 ]

* 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 [ 1461602-59-4 ]

[ 1461602-59-4 ] Synthesis Path-Downstream 1~23

1
[ 393-53-3 ]
[ 74-89-5 ]
[ 1461602-59-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	In 1,4-dioxane; water; at 140℃; for 14.0h;	3-Fluoroisonicotinic acid (3.00 g, 21.3 mmol) was dissolved in dioxane (6 mL) and 30% aqueous methylamine solution (22.0 g, 213 mmol) was added. The reaction solution was heated to 140C and stirred for 14 hours. Conc. hydrochloric acid (12 N, 3 mL) was added and the pH was adjusted to 3, filtered and the filter cake was dried to give 3-(methylamino)isonicotinic acid (3.00 g, as a yellow solid) with a yield of 93%. 1H NMR: (400 MHz, DMSO-d6) delta 8.46(br, 1H), 7.89(s, 1H), 7.69(d, J = 5.2 Hz, 1H), 7.50(d, J = 5.2 Hz, 1H), 2.80(s, 3H).
93%	In 1,4-dioxane; water; at 140℃; for 14.0h;	3-Fluoroisonicotinic acid (3.00 g, 21.3 mmol) was dissolved in dioxane (6 mL), and then 30% methylamine aqueous solution (22.0 g, 213 mmol) was added. The reaction solution was heated to 140 C. and then stirred for 14 hours. Concentrated hydrochloric acid (12N, 3 mL) was added to adjust the pH value to pH=3, followed by filtration. The filter cake was dried to give 3-(methylamino)isonicotinic acid (3.00 g, yellow solid) with a yield of 93%. 1H NMR: (400 MHz, DMSO-d6) delta8.46 (s, 1H), 7.89 (s, 1H), 7.69 (d, J=4.8 Hz, 1H), 7.50 (d, J=4.8 Hz, 1H), 2.80 (s, 3H).
42%	In 1,4-dioxane; water; at 125℃; for 9.5h;Microwave irradiation;	Example 153: 3-(methylamino)-4-pyridinecarboxylic acid Methylamine (0.321 mL,3.90 mmol, 40% solution in water) was added to a 3-fluoro-4- pyridinecarboxylic acid (250 mg, 1 .772 mmol) and 1 ,4-Dioxane (0.3 ml) and the mixture heated using a microwave to 125 C for 1.5 hr then 2 hr and finally an additional 6 hr. The mixture was allowed tocoolthen concentrated by evaporation. Water (10 ml) was added then the mixture acidifed to pH 3 using 37% HCI. The resulting bright yellow precipitate was filtered then washed with water (10 ml) to give the title compound as a yellow solid, 114 mg (42%).1H NMR (400 MHz, DMSO-S6) 8.2oppm (1H, 5), 7.84ppm (1H, d), 7.Ssppm (1H, d), 2.93ppm (3H, 5).

References: [1]Patent: EP3299371,2018,A1 .Location in patent: Paragraph 0543; 0544.
[2]Patent: US2018/148451,2018,A1 .Location in patent: Paragraph 0282; 0283.
[3]Patent: WO2013/143597,2013,A1 .Location in patent: Page/Page column 94.

2
[ 1461602-59-4 ]
1-methylpyrido[3,4-d]pyrimidine-2,4-dione [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .
[2]Patent: US2018/148451,2018,A1 .

3
[ 1461602-59-4 ]
3-(2-(2,4-dimethylthiazol-5-yl)ethyl)-1-methylpyrido[3,4-d]pyrimidine-2,4-dione [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

4
[ 1461602-59-4 ]
3-(3-(1H-indol-3-yl)propyl)-1-methylpyrido[3,4-d]pyrimidine-2,4-dione [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

5
[ 1461602-59-4 ]
1-methyl-3-(4-(3-methylisoxazol-5-yl)butyl)pyrido[3,4-d]pyrimidine-2,4-dione [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

6
[ 1461602-59-4 ]
3-(methylamino)isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25℃; for 24.0h;	3-(Methylamino)isonicotinic acid (4.00 g, 26.3 mmol), 1-hydroxybenzotriazole (10.7 g, 78.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (15.1 g, 78.9 mmol) and ammonium chloride (5.63 g, 105 mmol) were dissolved in N,N-dimethylformamide (5 mL). The reaction solution was stirred at 25C for 24 hours. The reaction was quenched by adding water (100 mL). The mixture was extracted with isopropanol / chloroform (1:3) (50 mL x 2). The organic phases were combined and concentrated under reduced pressure. The residue was added with dichloromethane / methanol (10:1, 30 mL), stirred for 10 minutes, filtered and the filter cake was dried to give 3-(methylamino)isonicotinamide (3.50 g, as a yellow solid) with a yield of 88%. 1H NMR: (400 MHz, DMSO-d6) delta 8.12-8.06(m, 2H), 7.80(d, J = 5.2 Hz, 1H), 7.62-7.61(br, 1H), 7.52-7.48(br, 1H), 7.43(d, J = 5.2 Hz, 1H), 2.84(d, J = 5.2 Hz, 3H).
88%	With ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25℃; for 24.0h;	3-(Methylamino)isonicotinic acid (4.00 g, 26.3 mmol), 1-hydroxybenzotriazole (10.7 g, 78.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (15.1 g, 78.9 mmol) and ammonium chloride (5.63 g, 105 mmol) were dissolved in N,N-dimethylformamide (5 mL). The reaction solution was stirred at 25 C. for 24 hours. The reaction was quenched by adding water (100 mL). The mixture was extracted with isopropanol/chloroform (1:3) (50 mL*2). The organic phases were combined, concentrated under reduced pressure. Methylene chloride/methanol (10:1, 30 mL) was added into the residue and then stirred for 10 minutes, followed by filtration. The filter cake was dried to give 3-(methylamino)isonicotinamide (3.50 g, yellow solid) with a yield of 88%. 1H NMR: (400 MHz, DMSO-d6) delta8.09 (s, 2H), 7.80 (d, J=5.2 Hz, 1H), 7.62-7.61 (m, 1H), 7.52-7.48 (m, 1H), 7.43 (d, J=5.2 Hz, 1H), 2.84 (d, J=5.2 Hz, 3H).

References: [1]Patent: EP3299371,2018,A1 .Location in patent: Paragraph 0543; 0545.
[2]Patent: US2018/148451,2018,A1 .Location in patent: Paragraph 0282; 0284.

7
[ 1461602-59-4 ]
1-methyl-3-(3-(3-methylisoxazol-5-yl)propyl)pyrido[3,4-d]pyrimidine-2,4-dione [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

8
[ 1461602-59-4 ]
3-(4-(benzofuran-3-yl)butyl)-1-methylpyrido[3,4-d]pyrimidine-2,4-dione [ No CAS ]

References: [1]Patent: EP3299371,2018,A1 .

9
[ 1461602-59-4 ]
3-((3-ethyloxetan-3-yl)methyl)-1-methylpyrido[3,4-d]pyrimidin-2,4-dione [ No CAS ]

References: [1]Patent: US2018/148451,2018,A1 .

10
[ 1461602-59-4 ]
1-methyl-3-((tetrahydrofuran-3-yl)methyl)pyrido[3,4-d]pyrimidin-2,4-dione [ No CAS ]

References: [1]Patent: US2018/148451,2018,A1 .

11
[ 1461602-59-4 ]
1-methyl-3-((tetrahydropyran-4-yl)methyl)pyrido[3,4-d]pyrimidin-2,4-dione [ No CAS ]

References: [1]Patent: US2018/148451,2018,A1 .

12
[ 1461602-59-4 ]
1-methyl-3-(2-(tetrahydropyran-4-yl)ethyl)pyrido[3,4-d]pyrimidin-2,4-dione [ No CAS ]

References: [1]Patent: US2018/148451,2018,A1 .

13
[ 1461602-59-4 ]
3-((4-methoxycyclohexyl)methyl)-1-methylpyrido[3,4-d]pyrimidin-2,4-dione [ No CAS ]

References: [1]Patent: US2018/148451,2018,A1 .

14
[ 1461602-59-4 ]
C₁₃H₁₅N₃O₃ [ No CAS ]

References: [1]Patent: US2018/148451,2018,A1 .

15
[ 1461602-59-4 ]
methyl 3-(N-methylacetamido)pyridine-4-carboxylate [ No CAS ]