912369-42-7|Methyl 3-((tert-butoxycarbonyl)amino)picolinate| Ambeed

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Quality Control of [ 912369-42-7 ] Purity: 96% SDS Specification

COA

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Product Details of [ 912369-42-7 ]

CAS No. :	912369-42-7
Formula :	C₁₂H₁₆N₂O₄
M.W :	252.27
SMILES Code :	O=C(OC)C1=NC=CC=C1NC(OC(C)(C)C)=O
MDL No. :	MFCD12026422
InChI Key :	AWHQAUKVCWXFSV-UHFFFAOYSA-N
Pubchem ID :	49760370

Safety of [ 912369-42-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 912369-42-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	6
Fraction Csp3	0.42
Num. rotatable bonds	6
Num. H-bond acceptors	5.0
Num. H-bond donors	1.0
Molar Refractivity	65.76
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	77.52 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.59
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	2.15
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.02
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.	0.76
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	1.15
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.73

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.61
Solubility	0.62 mg/ml ; 0.00246 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.41
Solubility	0.0981 mg/ml ; 0.000389 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.06
Solubility	0.221 mg/ml ; 0.000875 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	Yes
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.	-6.31 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	0.0
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	1.0 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<0.0
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)	2.63

Application In Synthesis of [ 912369-42-7 ]

* 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 [ 912369-42-7 ]

[ 912369-42-7 ] Synthesis Path-Downstream 1~16

1
[ 24195-07-1 ]
[ 24195-02-6 ]
[ 75-65-0 ]
[ 912369-42-7 ]
[ 873460-09-4 ]

Yield	Reaction Conditions	Operation in experiment
	With diphenyl phosphoryl azide; triethylamine; at 20℃; for 4.08333h;Heating / reflux;	methyl 3- [(fe^-butoxycarbonyl)aminolpyridine-2-carboxylate; To a mixture of 2- (methoxycarbonyi)nicotinic acid and 3-(methoxycarbonyl)pyridine-2-carboxylic acid (10.46 g, 57.7 mmol) is added tert-butanol (100 mL) and TEA (8.85 mL, 63.5 mmol). The reaction is stirred for five minutes at rt and then diphenyl phosphoryl azide (13.1 mL, 60.6 mmol) is added. The reaction is heated to reflux and stirred for approximately four hours. The reaction mixture is cooled to rt, concentrated to dryness, re-dissolved in EtOAc, and washed with water and saturated sodium bicarbonate (2 x 20 mL each). The organic layers are combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The mixture is purified by column chromatography (100% hexanes to 100% EtOAc) to yield the title compound and methyl 2-[(f°rt-butoxycarbonyl)amino]nicotinate (9.24 g, 64% yield). LCMS (ES, M+Na=275).

References: [1]Patent: WO2006/106326,2006,A1 .Location in patent: Page/Page column 129.

2
[ 912369-42-7 ]
[ 873460-09-4 ]
[ 877593-11-8 ]
[ 824429-51-8 ]

Yield	Reaction Conditions	Operation in experiment
		ter f-butyl f2-(hvdroxymethyl)py ridin-3-yll carbamate; To methyl 3-[(tert- butoxycarbonyl)amino]pyridine-2-carboxylate and methyl 2-[(tert- butoxycarbonyl)amino]nicotinate (5.00 g, 19.8 mmol) is added THF/MeOH (30 mL/3 mL) and the reaction is cooled to 0 C whereupon sodiumborohydride (1.49 g, 39.6 mmol) is added. The reaction is warmed to rt and stirred for four hours. The reaction mixture is then EPO <DP n="132"/>dissolved in EtOAc and washed with saturated sodium bicarbonate solution. The organic layers are combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford the title compound and tert-buty [3-(hydroxymethyl)pyridin-2- yljcarbamate which are separated by preparatory HPLC (5-95% MeCN/water/0.1% TFA). The desired isomer is confirmed by ID NOE NMR experiments. 1H NMR delta 8.78 (br s, IH), 8.17 (m, IH), 8.10 (d, IH), 7.27 (dd, IH), 4.64 (s, 2H), 1.46 (s, 9H). LCMS (ES, M+H=225).

References: [1]Patent: WO2006/106326,2006,A1 .Location in patent: Page/Page column 129-130.

3
[ 912369-42-7 ]
[ 36052-27-4 ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 2754 - 2761.

4
[ 24195-07-1 ]
[ 75-65-0 ]
[ 912369-42-7 ]

Yield	Reaction Conditions	Operation in experiment
38.5%		2-(Methoxycarbonyl)pyridine-3-carboxylic acid (3 g, 16.57 mmol) was dissolved in 50 mL of t-ButOH and 4 mL of TEA were added. The solution was stirred for 5 min at room temperature, then diphenylphosphorylazide (3.6 mL, 16.57 mmol) was added and the reaction was refluxed for 3 hours. The mixture was concentrated and the residue purified flash chromatography (silica) eluting with ethyl acetate in cyclohexane from 20 to 50%. The fractions containing the product were collected and concentrated in vacuo to give methyl 3-[(tert- butoxy)carbonyl]amino}pyridine-2-carboxylate (1.6 g, 38.5% yield).

References: [1]Patent: WO2016/196776,2016,A2 .Location in patent: Paragraph 00765.
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 2754 - 2761.

5
[ 912369-42-7 ]
methyl 3-[(tert-butoxy)carbonyl]amino}piperidine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With platinum(IV) oxide; hydrogen; acetic acid; under 3750.38 Torr; for 12h;	Methyl 3-[(tert-butoxy)carbonyl]amino}pyridine-2-carboxylate (1.53 g, 6.06 mmol) was dissolved in AcOH (30 mL). PtO2 (770 mg) was added and the mixture was stirred under H2 atmosphere (5 bar) for 12 hours. The catalyst was filtered off, the solvent was evaporated and the residue taken up with DCM (50mL) and washed with NaHCO3 aqueous saturated solution. The organic phase was concentrated to give methyl 3-[(tert-butoxy)carbonyl]amino}piperidine-2- carboxylate (1.42 g, 91 % yield) as diastereoisomeric mixture.

References: [1]Patent: WO2016/196776,2016,A2 .Location in patent: Paragraph 00766.

6
[ 912369-42-7 ]
methyl 3-[(tert-butoxy)carbonyl]amino}-1-(6-chloro-5-cyanopyrazin-2-yl)piperidine-2-carboxylate [ No CAS ]