6265-73-2|N-(2-Hydroxyethyl)nicotinamide| Ambeed

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Quality Control of [ 6265-73-2 ] Purity: 95% SDS Specification

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Product Details of [ 6265-73-2 ]

CAS No. :	6265-73-2
Formula :	C₈H₁₀N₂O₂
M.W :	166.18
SMILES Code :	C1=CC=NC=C1C(NCCO)=O
MDL No. :	MFCD00547113
InChI Key :	SJZLOWYUGKIWAK-UHFFFAOYSA-N
Pubchem ID :	72663

Safety of [ 6265-73-2 ]

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

Computational Chemistry of [ 6265-73-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	2.0
Molar Refractivity	43.2
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.	1.08
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	-0.11
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.2
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.	-0.6
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	0.59
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.15

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.91
Solubility	20.6 mg/ml ; 0.124 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.	-0.74
Solubility	30.0 mg/ml ; 0.18 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	-2.25
Solubility	0.93 mg/ml ; 0.0056 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.	-7.39 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)	1.26

Application In Synthesis of [ 6265-73-2 ]

* 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 [ 6265-73-2 ]

[ 6265-73-2 ] Synthesis Path-Downstream 1~35

1
[ 56-23-5 ]
[ 72676-16-5 ]
[ 6265-73-2 ]

References: [1]Journal of the American Chemical Society,1947,vol. 69,p. 200,203.

2
[ 93-60-7 ]
[ 141-43-5 ]
[ 6265-73-2 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1998,vol. 41,p. 605 - 614.
[2]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1579 - 1589.
[3]Chemische Berichte,1954,vol. 87,p. 1632.
[4]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 1041 - 1058.
[5]Patent: WO2007/38772,2007,A1 .Location in patent: Example 2; 3.

3
[ 6265-73-2 ]
[ 107-07-3 ]
1-(2-hydroxy-ethyl)-3-(2-hydroxy-ethylcarbamoyl)-pyridinium; chloride [ No CAS ]

References: [1]Chemische Berichte,1954,vol. 87,p. 1632.

4
[ 6265-73-2 ]
[ 72676-16-5 ]

References: [1]Journal of the American Chemical Society,1947,vol. 69,p. 200,203.

5
[ 6265-73-2 ]
[ 38953-47-8 ]
[ 130558-63-3 ]

References: [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 333 - 341.

6
[ 6265-73-2 ]
[ 5538-51-2 ]
[ 88354-02-3 ]
[ 88353-97-3 ]

References: [1]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1983,vol. 37,p. 351 - 359.

7
[ 6265-73-2 ]
[ 153-61-7 ]
2-<(3-pyridinylcarbonyl)amino>ethyl 7-(2-thienylacetamido)cephalosporante Δ² [ No CAS ]
[ 154777-98-7 ]

References: [1]Heterocycles,1994,vol. 37,p. 477 - 486.

8
[ 6265-73-2 ]
[ 61-33-6 ]
[ 122048-13-9 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 1774 - 1781.

9
[ 88598-33-8 ]
[ 59-67-6 ]
[ 6265-73-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 1063 - 1070.

10
[ 674-82-8 ]
[ 6265-73-2 ]
[ 129904-65-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1579 - 1589.

11
[ 6265-73-2 ]
[ 39262-24-3 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1998,vol. 41,p. 605 - 614.
[2]Archiv der Pharmazie,2003,vol. 336,p. 445 - 455.
[3]Archiv der Pharmazie,2003,vol. 336,p. 445 - 455.

13
[ 6265-73-2 ]
[ 112-29-8 ]
1-decyl-3-(2-hydroxy-ethylcarbamoyl)-pyridinium; bromide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 1041 - 1058.

14
[ 6265-73-2 ]
[ 76016-68-7 ]
N-[2-(4-phenyl-furazan-3-yloxy)-ethyl]-nicotinamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 1727 - 1732.

15
[ 6265-73-2 ]
[ 66074-00-8 ]
N-[2-(4-benzenesulfonyl-5-oxy-furazan-3-yloxy)-ethyl]-nicotinamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 1727 - 1732.

16
[ 6265-73-2 ]
[ 98384-57-7 ]
N-[2-(4-benzenesulfonyl-furazan-3-yloxy)-ethyl]-nicotinamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 1727 - 1732.

17
[ 6265-73-2 ]
[ 49558-03-4 ]
N-[2-(5-oxy-4-phenyl-furazan-3-yloxy)-ethyl]-nicotinamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 1727 - 1732.

18
[ 614-18-6 ]
[ 141-43-5 ]
[ 6265-73-2 ]

Yield	Reaction Conditions	Operation in experiment
96.6%		(A) A mixture of 1.6 kg of ethyl nicotinate,Ethanolamine 1.1kg into the reactor.The reaction was heated to 125 C for 4 hours.After completion of the reaction,Cooled to 100 C,Vacuum distillation,Vacuum distillation vacuum-0.091MPa distillation temperature rose to 130 ~ 135 when the end of distillation, the reaction solution;(B) The reaction solution can be rapidly cooled to 80 C with brine under stirring,And then slowly cooled to 65 ;(C) 1.6 kg of acetone was added dropwise at 60 C,After the dropwise addition was continued, the temperature was gradually lowered to 45 C,Crystal precipitation,And the mixture was stirred at 45 C for 1 hour.(D) continue to cool to 30 C,Stir for 1.5 hours,And then continue to cool to 10-15 ,Stirred for 1 hour,And then continue to cool to 0 or so,Stirring crystallization after 1 hour out.Centrifugation,The filter cake,The oven was dried at 50-60 & lt; 0 & gt; C,To obtain 1.70 kg of white N- (2-hydroxyethyl) -nicotinamide,The overall yield was 96.6%Mp 89-91 C.
64.5%		EXAMPLE 91 Preparation of N-(2-Hydroxyethyl)-3-pyridinecarboxamide A neat mixture of 2-aminoethanol (6.1 g, 0.10 mol) and ethyl nicotinate (15.1 g, 0.10 mol) was refluxed overnight. As the mixture was cooled to room temperature, the product precipitated as a crystalline solid. It was filtered, washed with ether and then recrystallized from 2-propanol/ether. The final productproduct was collected by vacuum filtration and washed with ether. The dried, white compound weighed 10.7 g, resulting in a 64.5% yield; mp 88.5-89.5 C. (lit. value 92 C.).
64.5%		EXAMPLE 91 Preparation of N-(2-Hydroxyethyl)-3-pyridinecarboxamide A neat mixture of 2-aminoethanol (6.1 g, 0.10 mol) and ethyl nicotinate (15.1 g, 0.10 mol) was refluxed overnight. As the mixture was cooled to room temperature, the product precipitated as a crystalline solid. It was filtered, washed with ether and then recrystallized from 2-propanol/ether. The final productproduct was collected by vacuum filtration and washed with ether. The dried, white compound weighed 10.7 g, resulting in a 64.5% yield; mp 88.5-89.5 C. (lit. value 92 C).

64%	at 20 - 55℃; for 18h;	General procedure: For the synthesis of the hydroxylated precursors, ethanolamine (1.5 mmol) was added slowly to the esters (1 mmol) at 55C and stirred for 3 h. The reaction mixture was stirred at room temperature for 15 h. The residue was purified by silica gel column chromatography (eluent/ethyl acetate/hexane 8:2) or recrystallized from ethyl acetate. The progress of the reaction was monitored by TLC.`
42%	In toluene; at 80℃; for 48h;	Ethyl nicotinate (15.1 g, 100.0 mmol, 1.0 eq.) and Ethanolamine (6.1 g, 100.0 rnrnol, 1.0 eq.) were dissolved in toluene (80 ml_). The reaction mixture was heated to 80 0C and stirred for 48 h. During the reaction the mixture changed into a sticky emulsion. The emulsion was cooled down to room temperature and the lower phase became solid. The upper liquid phase was decanted and the orange solid was crystallised twice, first from ethyl acetate and then from acetone. The crystals were dried under high vacuum at room temperature to give 7.1 g (42 %) of the product as a white, free flowing powder. The 1 H NMR and the 13C NMR corresponds to the literature (Ogawa, T.; Hatayama, K.; Maeda, H.; Kita, Y. Chem. Pharm. Bull. 1994, 42 (8) 1579-1589). 1H NMR (CDCI3) delta = 3.60-3.64 (q, 2H), 3.82-3.85 (t, 2H), 4.00 (s, 1H), 7.33-7.39 (m, 2H), 8.10-8.14 (m, 1H), 8.64-8.67 (q, 1 H)1 8.99-9.00 (t, 1 H). 13C NMR (CDCI3) delta = 42.8, 61.5, 123.6, 130.2, 135.5, 147.8, 152.0, 166.4.
		EXAMPLE 58 Preparation of N-(2-Hydroxyethyl)-3-pyridinecarboxamide A solution of 49.2 g (0.32525 mol) ethyl nicotinate and 72 g (1.17 mol) ethanolamine was heated at 70 C. for 60 hours. The excess ethanolamine was removed under reduced pressure and the resulting viscous cream oil was stirred with ether for 48 hours. The resulting white solid was removed by filtration, affording 46 g (85.1%) of the title compound melting at 75-78 C.
		EXAMPLE 58 Preparation of N-(2-Hydroxyethyl)-3-pyridinecarboxamide A solution of 49.2 g (0.32525 mol) ethyl nicotinate and 72 g (1.17 mol) ethanolamine was heated at 70 C. for 60 hours. The excess ethanolamine was removed under reduced pressure and the resulting viscous cream oil was stirred with ether for 48 hours The resulting white solid was removed by filtration, affording 46 g 15 (85 1%) of the title compound melting at 75-78 C.

References: [1]Patent: CN105218441,2016,A .Location in patent: Paragraph 0069; 0070; 0071; 0072; 0073.
[2]Patent: US4983586,1991,A .
[3]Patent: US5017566,1991,A .
[4]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2783 - 2790.
[5]Patent: WO2007/39059,2007,A1 .Location in patent: Page/Page column 23.
[6]Archiv der Pharmazie,2003,vol. 336,p. 445 - 455.
[7]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 808 - 816.
[8]Patent: US4983586,1991,A .
[9]Patent: US5017566,1991,A .
[10]Organic Letters,2016,vol. 18,p. 3434 - 3437.

19
[ 6265-73-2 ]
[ 50412-70-9 ]
3-methyl-4-[2-(3-pyridineformamido)ethoxycarbonyl]furoxan [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 808 - 816.

20
[ 59-67-6 ]
[ 141-43-5 ]
[ 6265-73-2 ]

Yield	Reaction Conditions	Operation in experiment
86%		Example 4; Preparation of (R)-4-trimethyIammonium-3-(tetradecylcarbamoyl)-amino- butyrate of {2[-(N-methyl-(1 ,4-dihydro-pyridine)-3-yl)carbonyl]-amino}ethyliodide (ST3496); Preparation of the intermediate N-(2-hvdroxy-ethvD-nicotinamide; SOCb (455 mul, 6.26 mmol) ) was added to a suspension of nicotinic acid (0.385 g, 3.13 mmol) in anhydrous toluene (15 ml) and the reaction mixture was refluxed at 1400C for 4 hours. Then the clear solution was cooled and the solvent was removed under vacuum. The solid residue was washed three times with diethyl ether and fresh anhydrous toluene (15 ml) and ethanolamine (756 mul, 12.52 mmol) were added. The mixture was warmed up to 500C overnight. EPO <DP n="18"/>Then the solvent was removed under vacuum and the solid residue was purified by silica gel chromatography using as eluent dichloromethane/methanol 9.2/0.8. The desired product was obtained as a white solid (450 mg, 86% yield), m.p. = 84.5-85.50C; 1H NMR (300MHz, DMSOd6) delta: 9.00 (s, 1H, NH), 8.68, (m, 2H, Ar), 8.17 (d, 1H, Ar), 7.60 (m, 1H1 Ar), 4.74 (m, 1H, OH), 3.51 (m, 2H, CH2), 3.36 (m, 2H1 CH2).
77%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0℃; for 24h;	General procedure: To obtain the alcohol derivatives, an esterification or amidation with the corresponding benzoic acid (1equiv) was carried out in 20mL anhydrous CH2Cl2 at 0C using the corresponding alcohol or amine (1.0equiv), EDC·HCl (1.5equiv), and DMAP or HOBt (0.2equiv). After the reaction was completed (TLC control) a subsequent purification by flash-chromatography was performed to obtain compounds 10q-u
0.76 g	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; for 12h;Inert atmosphere;	A solution of ethanolamine (2.44g, 40mmol) in tetrahydrofuran (200mL) and EDC·HCl(1.84g, 9.6mmol), HOBT(1.08g, 8.0mmol) was stirred at room temperature and to it nicotinic acid (1.0g, 8.0mmol) was added in several portions. Upon completion of the reaction, the solution was washed with distilled water once (100mL). Extraction of the ester was effected with chloroform (×3). The combined chloroform extracts were dried on anhydrous Na2SO4, decanted and evaporated. Purification was obtained by chromatography on flash silica (chloroform/methanol 20/1). Compound A4 (0.76g) was obtained as a yellow oil. Yield: 59%.1 IR (KBr,cm-1): 3330(s), 2924(s), 1541(vs), 1165(m), 1014(m), 736(m). 1H NMR(400MHz, CDCl3-d) delta 9.01(s, 1H), 8.65(s, 1H), 8.14(d, J=6.6Hz, 1H), 7.49(s, 1H), 7.36(s, 1H), 3.92(s, 1H), 3.83(s, 2H), 3.62(s, 2H). 13C NMR(101MHz, CDCl3-d) delta 166.3, 151.8, 147.7, 135.6, 130.2, 123.7, 61.4, 42.8. ESI-HRMS(m/z): Calcd. for C8H10N2O2 [M+H]+: 167.0732; found 167.0821.

References: [1]Patent: WO2006/92204,2006,A1 .Location in patent: Page/Page column 16-17.
[2]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 5134 - 5147.
[3]Archiv der Pharmazie,2003,vol. 336,p. 445 - 455.
[4]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3307 - 3318.

21
[ 6265-73-2 ]
[ 100-11-8 ]
1-(4-nitrobenzyl)-3-[N-(2-hydroxyethyl)carbamoyl]pyridinium bromide [ No CAS ]

References: [1]Archiv der Pharmazie,2003,vol. 336,p. 445 - 455.

22
[ 6265-73-2 ]
[ 33005-95-7 ]
[ 761415-94-5 ]