210366-15-7|1-(Benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxylic acid| Ambeed

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Quality Control of [ 210366-15-7 ] Purity: 96% SDS Specification

COA

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NMR

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Product Details of [ 210366-15-7 ]

CAS No. :	210366-15-7
Formula :	C₁₃H₁₁NO₄
M.W :	245.23
SMILES Code :	O=C(C1=CC=CC(N1OCC2=CC=CC=C2)=O)O
MDL No. :	MFCD20270106
InChI Key :	CIUDQXNWTGQYIC-UHFFFAOYSA-N
Pubchem ID :	15450555

Safety of [ 210366-15-7 ]

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

Computational Chemistry of [ 210366-15-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	12
Fraction Csp3	0.08
Num. rotatable bonds	4
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	64.59
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	68.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.7
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	1.67
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.02
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.	2.01
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	1.33
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.55

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.64
Solubility	0.559 mg/ml ; 0.00228 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.	-2.72
Solubility	0.464 mg/ml ; 0.00189 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	-3.15
Solubility	0.174 mg/ml ; 0.00071 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.	-6.61 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.	0.56

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)	2.54

Application In Synthesis of [ 210366-15-7 ]

* 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 [ 210366-15-7 ]

[ 210366-15-7 ] Synthesis Path-Downstream 1~35

1
[ 210366-13-5 ]
[ 210366-15-7 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. 13 - 19.

2
[ 210366-15-7 ]
[ 210366-17-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With oxalyl dichloride;N,N-dimethyl-formamide; at 40℃; for 4 - 6h;	1,2-HOPOBn acid chloride; To a suspension of 1 ,2-HOPOBn acid (5 0 g, 20 mmol) in toluene or benzene (50-70 mL), excess of oxalyl chloride (2 0 g) was added with stirring A lot of gas bubbles evolved and the suspension turned to be clear upon the addition of a drop of DMF as catalyst The mixture was then warmed to 40 C (oil bath temperature) for 4-6 hr, and the solvent was moved on a rotovap to leave pale yellow oil The residual solvent and oxallyl chloride were removed in a vacuum line (0 1 mm Hg) when the oil solidified as pale yellow crystalline <n="60"/>solid, raw yield 5.O g (95%). It is generally used directly for next step reaction without further purification.[0222] 1 H NMR(SOOMHZ5 CDCI3)^ 5.32(S, 2H), 6.88(d, l H), 6.94(d, I H), 7.3-7.4(m,4H), 7.49(m, 2H). 1 3C NMR(75 MHz, CDCl3): delta 78.5, 1 12.3, 128.4, 128.6, 129.4, 130.3, 132.7, 136.4, 140.2, 158.1 , 1 58.8.
95%	With oxalyl dichloride;N,N-dimethyl-formamide; In toluene; at 60℃; for 4 - 6h;	To a suspension of bezyloxyl,2-HOPO carboxylic acid (5.0 g, 20 mmol) in toluene or benzene (50-70 mL), excess oxalyl chloride (5.0 g) was added while stirring. Gas was evolved and the suspension became clear upon the addition of a drop of DMF as a catalyst. The mixture was then warmed to 60 C. (oil bath) for 4-6 h. The solvent was removed by rotary evaporation, leaving a pale brown oil. After co-evaporation twice with toluene (5 mL), the residue was dissolved in dry THF, passed though a flash silica gel plug and eluted with dry THF. The 1,2-HOPOBn acid chloride so obtained after the solvent was removed under reduced pressure, was a thick, pale yellow oil: crude yield 5.0 g (95%). The crude product was used directly for reaction without further purification. 1H NMR (300 MHz, CDCl3): delta5.32 (s, 2H, CH2), 6.88(d, J=7.0 Hz, 1 H), 6.726(d, J=9.0 Hz, 1 H), 7.32-7.51(m, 6 H). 13C NMR (125 MHz, DMSO-d6): delta 78.5, 112.2, 128.5, 128.6, 129.4, 130.3, 132.7, 136.4, 140.1, 158.1, 158.8.
95%	With oxalyl dichloride; N,N-dimethyl-formamide; at 60℃; for 4 - 6h;	(4) Synthesis of 1 ,2-HOPOBn acid chloride 37A[0371] To a suspension of bezyloxyl,2-HOPO carboxylic acid (5.0 g, 20 mmol) in toluene or benzene (50-70 mL), excess oxalyl chloride (5.0 g) was added while stirring. Gas was evolved and the suspension became clear upon the addition of a drop of DMF as a catalyst. The mixture was then warmed to 60 0C (oil bath) for 4-6 h. The solvent was removed by rotary evaporation, leaving a pale brown oil. After co-evaporation twice with toluene (5 mL), the residue was dissolved in dry THF, passed though a flash silica gel plug and eluted with dry THF. The 1 , 2-HOPOBn acid chloride so obtained after the solvent was removed under reduced pressure, was a thick, pale yellow oil: crude yield 5.0 g (95%). The crude product was used directly for reaction without further purification. 1H NMR (300MHz, CDCl3): 55.32 (s, 2H, CH2), 6.88(d, J = 7.0 Hz, 1 H), 6.726(d, J = 9.0 Hz, 1 H), 7.32-7.51(m, 6 H). 13C NMR (125MHz, DMSO-d6): delta 78.5, 1 12.2, 128.5, 128.6, 129.4, 130.3, 132.7, 136.4, 140.1 , 158.1, 158.8.

	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;	0.9 mL of oxalyl chloride (10 mmol) was added dropwise to a solution of 1.79 g of 5 (7.3 mmol) in CH2Cl2 (15 mL). After adding a drop of DMF, the mixture was stirred until the end of HCl release.
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 3h;	Oxalyl chloride (1.1 g, 8.7 mmol) was added to a suspension of 7 (1.11 g, 4.52 mmol) in dichloromethane (40 mL), followed by 1 drop of dry DMF. The solution became homogenous within 30 mm, and the reaction was stirred at room temperature for 3 hours total. The solvent was then removed under vacuum overnight. The residue was dissolved into dichloromethane (20 mL) and added dropwise to a solution of 6 (1.13 mmol) dissolved in dichloromethane (20 mL) and 40% aqueous K2C03 (20 mL) at 0 C with vigorous stirring. The reaction was stirred with warming to room temperature overnight. The dichloromethane layer was loaded directly onto a 4 inch tall x 1 inch wide silica gel column. Following a methanol/dichloromethane gradient elution, the desired product was collected using 4% methanol in dichloromethane. The solvent was removed under vacuum to yield the desired product as a hardened glass of 7. Yield: 520 mg, 36% over two steps. ?H NMR (600 MI-Tz, CDC13) oe 9.60 - 8.98 (m, 2H), 8.43 - 7.83 (m, 4H), 7.80 - 7.05 (m, 20H), 7.05 - 5.54 (m, 8H), 5.49 - 4.98 (m, 6H), 4.98 - 4.69 (m, 2H), 4.28 - 3.98 (m, 2H), 3.93 - 2.75 (m, 14H), 2.05 - 1.16 (m, 1OH). HRMS-ESI (m/z, [M+Hj) Calcd for C68H69N,00,5: 1265.4938, Found:1265.4901.

References: [1]Patent: WO2008/8797,2008,A2 .Location in patent: Page/Page column 58-59.
[2]Patent: US2005/8570,2005,A1 .Location in patent: Page/Page column 45.
[3]Patent: WO2007/121453,2007,A2 .Location in patent: Page/Page column 109.
[4]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. 13 - 19.
[5]Journal of Medicinal Chemistry,2002,vol. 45,p. 3963 - 3971.
[6]Tetrahedron,2008,vol. 64,p. 11319 - 11324.
[7]Australian Journal of Chemistry,2009,vol. 62,p. 1300 - 1307.
[8]Journal of the American Chemical Society,2011,vol. 133,p. 7942 - 7956.
[9]Tetrahedron Letters,2011,vol. 52,p. 3973 - 3977.
[10]Journal of Medicinal Chemistry,2014,vol. 57,p. 4849 - 4860.
[11]Journal of the American Chemical Society,2015,vol. 137,p. 2816 - 2819.
[12]Patent: WO2018/45385,2018,A1 .Location in patent: Paragraph 00194; 00200.
[13]Chemical Science,2019,vol. 10,p. 6834 - 6843.

3
[ 100-44-7 ]
[ 94781-89-2 ]
[ 210366-15-7 ]

Yield	Reaction Conditions	Operation in experiment
91%		l-Benzyloxy-6-carboxy-2(lJ/)-pyridinone (1,2-HOPOBn acid); l -Hydroxy-6-carboxy-2(l H)-py?dinone (15 5 g, 0 1 mol) and anhydrous potassium carbonate (27 6 g, 0 2 mol) were mixed with benzyl chloride (15 2 g, 0 12 mol) in methanol (250 mL) The mixture was refluxed for 16 h, filtered, and the filtrate evaporated to dryness The residue was dissolved in water (50 ml ) and acidified with 6 N HCl to pH 2 The white precipitate was isolated by filtration, washed with cold water, and dried in vacuum to yield 22 3 g (91 %) of l -Benzyloxy-6-carboxy-2( l //)-py?dinone, mp 176- 177 0C[0220] 1 H NMR(300MHz, CDCI3) delta 5 269(s, 2H), 6 546(dd, J=I 6 Hz, J= 6 7 Hz, I H),6 726(dd, J=I 6Hz, J=9 2 Hz, I H), 7 39-7 51 (m, 6H) 1 3C NMR(75 MHz, DMSO-*) delta 77 9, 106 0, 124 1 , 128 5, 129 1 , 129 6, 133 8, 138 7, 140 5, 157 7, 161 7 Anal Calcd (Found) for C13H1 1NO4 C, 63 66 (63 75), H, 4 53 (4 55), N, 5 71 (5 52)
91%		(3) Synthesis of l-Benzyloxy-6-carboxy-2(lH)-pyridinone 36A[0370] 35A (15.5 g, 0.1 mol) and anhydrous potassium carbonate (27.6 g, 0.2 mol) was mixed with benzyl chloride (15.2 g, 0.12 mol) in methanol (250 mL). The mixture was refluxed for 16 h, filtered, and the filtrate was evaporated to dryness. The residue was dissolved in water (50 mL) and acidified with 6 N HCl to pH 2. The resulting white precipitate was isolated by filtration, washed with cold water, and dried in vacuum to yield 22.3 g (91 %) of 36A, mp 176-177 0C. Anal. Calc'd. (Found) for C13H1 1NO4: C, 63.66 (63.75); H, 4.53 (4.55), N, 5.71 (5.52). 1H NMR (500MHz, DMSO-d6): delta 5.26 (s, 2H, CH2), 6.54 (dd, J = 6.7, 1.1 Hz, 1 H), 6.73 (dd, J = 9.2, 1.6Hz, 1 H), 7.39-7.51 (m, 6 H). 13C NMR (125MHz, DMSO-dbeta): delta 77.9, 106.0. 124.1. 128.5, 129.1 , 129.6, 133.8, 138.7, 140.4, 157.6, 161.7.

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 4849 - 4860.
[2]Journal of Medicinal Chemistry,2002,vol. 45,p. 3963 - 3971.
[3]Patent: WO2008/8797,2008,A2 .Location in patent: Page/Page column 58.
[4]Patent: WO2007/121453,2007,A2 .Location in patent: Page/Page column 108.
[5]Patent: WO2017/105565,2017,A2 .Location in patent: Paragraph 0109.
[6]Dalton Transactions,2019,vol. 48,p. 3459 - 3466.

4
[ 530-62-1 ]
[ 210366-15-7 ]
1-benzyloxy-6-(imidazole-1-carbonyl)-1<i>H</i>-pyridin-2-one [ No CAS ]

References: [1]Environmental Science and Technology,2005,vol. 39,p. 1332 - 1337.

5
[ 96-53-7 ]
[ 210366-15-7 ]
[ 770738-07-3 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 10648 - 10649.

6
[ 210366-15-7 ]
[ 910106-58-0 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 10648 - 10649.

7
[ 210366-15-7 ]
[ 910106-57-9 ]

References: [1]Journal of the American Chemical Society,2006,vol. 128,p. 10648 - 10649.

8
[ 210366-15-7 ]
C₁₉H₂₆N₂O₆Si [ No CAS ]

References: [1]Environmental Science and Technology,2005,vol. 39,p. 1332 - 1337.

9
[ 19621-92-2 ]
[ 210366-15-7 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3963 - 3971.
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4849 - 4860.
[3]Patent: WO2017/105565,2017,A2 .
[4]Patent: WO2007/121453,2007,A2 .

10
[ 210366-15-7 ]
[ 110874-36-7 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3963 - 3971.
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4849 - 4860.
[3]Journal of the American Chemical Society,2015,vol. 137,p. 2816 - 2819.
[4]Patent: WO2007/121453,2007,A2 .

11
[ 210366-15-7 ]
3,4,3-LI-(1,2-Me-3,2-HOPO) [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3963 - 3971.

12
[ 210366-15-7 ]
[ 460986-08-7 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3963 - 3971.
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 4849 - 4860.
[3]Patent: WO2007/121453,2007,A2 .

13
[ 210366-15-7 ]
[ 460986-10-1 ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3963 - 3971.
[2]Patent: WO2007/121453,2007,A2 .

14
[ 94781-89-2 ]
[ 210366-15-7 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. 13 - 19.

15
[ 210366-10-2 ]
[ 210366-15-7 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2001,vol. 44,p. 13 - 19.

16
[ 1094194-45-2 ]
[ 100-44-7 ]
[ 210366-15-7 ]

Yield	Reaction Conditions	Operation in experiment
91%		35A (15.5 g, 0.1 mol) and anhydrous potassium carbonate (27.6 g, 0.2 mol) was mixed with benzyl chloride (15.2 g, 0.12 mol) in methanol (250 mL). The mixture was refluxed for 16 h, filtered, and the filtrate was evaporated to dryness. The residue was dissolved in water (50 mL) and acidified with 6 N HCl to pH 2. The resulting white precipitate was isolated by filtration, washed with cold water, and dried in vacuum to yield 22.3 g (91%) of 36A, mp 176-177 C. Anal. Calc'd. (Found) for C13H11NO4: C, 63.66 (63.75); H, 4.53 (4.55), N, 5.71 (5.52). 1H NMR (500 MHz, DMSO-d6): delta 5.26 (s, 2H, CH2), 6.54 (dd, J=6.7, 1.1 Hz, 1 H), 6.73 (dd, J=9.2, 1.6Hz, 1 H), 7.39-7.51 (m, 6 H). 13C NMR (125 MHz, DMSO-d6): delta 77.9, 106.0, 124.1, 128.5, 129.1, 129.6, 133.8, 138.7, 140.4, 157.6, 161.7.

References: [1]Patent: US2005/8570,2005,A1 .Location in patent: Page/Page column 44-45.

17
[ 140-75-0 ]
[ 210366-15-7 ]
C₂₀H₁₇FN₂O₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1063 - 1074.

18
[ 210366-15-7 ]
[ 1297532-40-1 ]

References: [1]Journal of the American Chemical Society,2011,vol. 133,p. 7942 - 7956.

19
[ 210366-15-7 ]
C₂₇H₃₃N₃O₈ [ No CAS ]

References: [1]Journal of the American Chemical Society,2011,vol. 133,p. 7942 - 7956.

20
[ 210366-15-7 ]
[ 1297532-42-3 ]

References: [1]Journal of the American Chemical Society,2011,vol. 133,p. 7942 - 7956.

21
[ 210366-15-7 ]
[ 1325717-74-5 ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 3973 - 3977.

22
[ 94781-88-1 ]
[ 210366-15-7 ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 2816 - 2819.

23
[ 21190-87-4 ]
[ 210366-15-7 ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 2816 - 2819.

24
[ 100-39-0 ]
[ 94781-89-2 ]
[ 210366-15-7 ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 2816 - 2819.

25
C₄₂H₅₂N₆O₆ [ No CAS ]
[ 210366-15-7 ]
C₆₈H₇₀N₈O₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With dmap; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 30h;	3,4,3-LI-IAMBn (7) (362 mg, 491 mumol), 1,2-HOPOBn (9) [16](289 mg, 1.18 mmol), DMAP (5.4 mg, 44 mumol), TBTU (379 mg,1.18 mmol) were suspended in 20 mL DCM. DIPEA (254 mg,1.96 mmol, 343 muL, rho 0.74 g/cm3) was added to start the reaction andit was stirred at roomtemperature for 30 h until TLC showed no furtherconversion. After the removal of the solvent under reduced pressure,the crude product was subjected to column chromatography (SiO2,gradient from 0% to 10% MeOH in DCM) to afford a white solid. Yield:394 mg (67%). ESI MS, LC-ESI MS data as well as TLC experiments indicatedpartial cleavage of benzyl protecting groups during the purificationstep. Thus the crude (8) was used directly in the next step. p-ESIHRMS (MeOH): 1191.5160 (calc. 1191.5186, [C68H71N8O12]+);1213.4967 (calc. 1213.5005, [C68H70N8NaO12]+); 1229.4748 (calc.1229.4745, [C68H70N8KO12]+).

References: [1]Journal of Inorganic Biochemistry,2016,vol. 162,p. 263 - 273.

26
[ 6066-82-6 ]
[ 210366-15-7 ]
2,5-dioxopyrrolidin-1-yl1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxylate [ No CAS ]

References: [1]Dalton Transactions,2017,vol. 46,p. 4749 - 4758.

27
[ 79-37-8 ]
[ 210366-15-7 ]
[ 210366-17-9 ]

References: [1]Patent: WO2017/105565,2017,A2 .Location in patent: Paragraph 0109.

28
[ 210366-15-7 ]
1-benzyloxy-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid methylamide [ No CAS ]

References: [1]Dalton Transactions,2017,vol. 46,p. 4749 - 4758.

29
[ 210366-15-7 ]
C₇H₈N₂O₃ [ No CAS ]

References: [1]Dalton Transactions,2017,vol. 46,p. 4749 - 4758.

30
C₅₀H₆₆N₁₀O₁₂ [ No CAS ]
[ 210366-15-7 ]
C₇₆H₈₄N₁₂O₁₈ [ No CAS ]

References: [1]Patent: WO2018/45385,2018,A1 .Location in patent: Paragraph 00238.
[2]Patent: WO2019/173639,2019,A1 .Location in patent: Paragraph 00322.
[3]Patent: WO2019/246311,2019,A1 .Location in patent: Paragraph 00396.

31
[ 19621-92-2 ]
[ 210366-15-7 ]