521980-82-5|Dimethyl 5-bromopyridine-2,3-dicarboxylate| Ambeed

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Quality Control of [ 521980-82-5 ] Purity: 95% SDS Specification

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Product Details of [ 521980-82-5 ]

CAS No. :	521980-82-5
Formula :	C₉H₈BrNO₄
M.W :	274.07
SMILES Code :	COC(=O)C1=CC(Br)=CN=C1C(=O)OC
MDL No. :	MFCD09953248
InChI Key :	JYRYOIMMYLBBNZ-UHFFFAOYSA-N
Pubchem ID :	53423993

Safety of [ 521980-82-5 ]

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

Computational Chemistry of [ 521980-82-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	4
Num. H-bond acceptors	5.0
Num. H-bond donors	0.0
Molar Refractivity	54.5
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	65.49 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.33
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	1.58
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.42
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.	1.01
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	1.81
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.63

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.57
Solubility	0.743 mg/ml ; 0.00271 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.	-2.57
Solubility	0.744 mg/ml ; 0.00272 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	-3.03
Solubility	0.256 mg/ml ; 0.000935 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	Yes
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.	-6.85 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)	2.11

Application In Synthesis of [ 521980-82-5 ]

* 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 [ 521980-82-5 ]

[ 521980-82-5 ] Synthesis Path-Downstream 1~35

1
[ 67-56-1 ]
[ 89-00-9 ]
[ 521980-82-5 ]

Yield	Reaction Conditions	Operation in experiment
63%		To a suspension of pyridine-2,3-dicarboxylic acid (50 g, 300 mmol) in MeOH (500 mL) was added concentrated H2SO4 (10 mL) slowly. The mixture was heated at reflux for 48 h, then cooled to 40 C, followed by the dropwise addition of Br2 (38 mL, 750 mmol) over 2 h. The reaction was heated at 55 C for 48 h, and then concentrated in vacuo. The residue was dissolved in isopropyl acetate (500 mL), and the resulted solution was washed with saturated aqueous a2S203 (200 mL x 4), followed by brine (400 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 5/1) to give the title compound as a yellow solid (52 g, 63%). MS (ESI, pos. ion) m/z: 274.0 [M + H]+; FontWeight="Bold" FontSize="10" H NMR (400 MHz, CDC13) delta (ppm): 8.75-8.76 (d, J= 2.2 Hz, 1H), 8.23-8.24 (d, J= 2.2 Hz, 1H), 3.93 (s, 1H), 3.89 (s, 1H).
63%		A solution of pyridyl 2,3-dicarboxylic acid (50 g, 300 mmol)Suspended in methanol (500 mL)To this was slowly added concentrated sulfuric acid (10 mL).After the mixture was refluxed for 48 hours,Cooled to 40 C, within 2 hours,To this was added bromine (38 mL, 750 mmol).The reaction solution was stirred at 55 C for 48 hours,Concentrated under reduced pressure.The residue was dissolved in isopropyl acetate (500 mL) and the resulting solution was obtainedThe residue was washed with sodium thiosulfate saturated solution (200 mL x 4), brine (400 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure.The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 5/1) to give the title compound as a yellow solid (52 g, 63%)
		Method II:; Step A: Dimethyl 5-bromopyridine-2,3-dicarboxylate; Concentrated sulfuric acid (1 L, 18.7 mol) was added slowly over 10 min to a suspension of pyridine-2,3-dicarboxylic acid (5.00 kg, 29.9 mol) in methanol (50 L), dissolving the suspension. The resulting mixture was heated at reflux for 48 h then cooled to 40 C. Bromine (8.0 kg, 50 mol) was added slowly over 2 h in 1-kg portions, keeping the temperature below 55 C. The reaction mixture was then heated at 55 C. for 24 h, cooled to 50 C. and additional Br2 (4.0 kg, 25 mol) was added slowly over 1 h in 1-kg portions, keeping temperature below 55 C. The reaction mixture was heated at 55 C. for 24 h, concentrated to a minimum volume (internal temp 30 C., solution may occasionally foam), then diluted with isopropyl acetate (50 L) and washed with a saturated aqueous sodium sulfite solution (3×20 L) (final extract is pH 8) followed by water (20 L). The organic layer was concentrated to approximately 15 L then diluted with heptane (40 L). The resulting slurry was stirred for 24 h at 23 C. The solids were filtered, washed with heptane (10 L), and dried to give the title compound.

		INTERMEDIATE 1; 3.-Methyl-2 5,-do o-5J-dhvdros iro cyclo enta 1 yridine-6.4'-imida^olidiacid; Step A: Dimethyl S-bromopyridine-2,3-dicarboxylate; Concentrated sulfuric acid (1 L, 18.7 mol) was added slowly over 10 min to a suspension of pyridine-2,3-dicarboxylic acid (5.00 kg, 29.9 mol) in methanol (50 L), dissolving the suspension. The resulting mixture was heated at reflux for 48 h then cooled to 40 C.Bromine (8.0 kg, 50 mol) was added slowly over 2 h in 1-kg portions, keeping the temperature below 55 C. The reaction mixture was then heated at 55 C for 24 h, cooled to 50 C and additional Br2 (4.0 kg, 25 mol) was added slowly over 1 h in 1-kg portions, keeping temperature below 55 C. The reaction mixture was heated at 55 C for 24 h, concentrated to a minimum volume (internal temp ~30 C, solution may occasionally foam), then diluted with isopropyl acetate (50 L) and washed with a saturated aqueous sodium sulfite solution (3 x 20 L) (final extract is ~ pH 8) followed by water (20 L). The organic layer was concentrated toapproximately 15 L then diluted with heptane (40 L). The resulting slurry was stirred for 24 h at 23 C. The solids were filtered, washed with heptane (10 L)? and dried to give the title compound.
		Step A: Dimethyl 5-bromopyridine-2,3-dicarboxylate Concentrated sulfuric acid (1 L, 18.7 mol) was added slowly over 10 min to a suspension of pyridine-2,3-dicarboxylic acid (5.00 kg, 29.9 mol) in methanol (50 L), dissolving the suspension. The resulting mixture was heated at reflux for 48 h then cooled to 40 C. Bromine (8.0 kg, 50 mol) was added slowly over 2 h in 1-kg portions, keeping the temperature below 55 C. The reaction mixture was then heated at 55 C for 24 h, cooled to 50 C and additional Br2 (4.0 kg, 25 mol) was added slowly over 1 h in 1-kg portions, keeping temperature below 55 C. The reaction mixture was heated at 55 C for 24 h, concentrated to a minimum volume (internal temp ~30 C, solution may occasionally foam), then diluted with isopropyl acetate (50 L) and washed with a saturated aqueous sodium sulfite solution (3 x 20 L) (final extract is ~pH 8) followed by water (20 L). The organic layer was concentrated to approximately 15 L then diluted with heptane (40 L). The resulting slurry was stirred for 24 h at 23 C. The solids were filtered, washed with heptane (10 L), and dried to give the title compound.
		Step A: Dimethyl 5-bromopyridine-2,3-dicarboxylate Concentrated sulfuric acid (1 L, 18.7 mol) was added slowly over 10 min to a suspension of pyridine-2,3-dicarboxylic acid (5.00 kg, 29.9 mol) in MeOH (50 L), dissolving the suspension. The resulting mixture was heated at reflux for 48 h then cooled to 40 C. Bromine(8.0 kg, 50 mol) was added slowly over 2 h in 1-kg portions, keeping the temperature below 55 C. The reaction mixture was then heated at 55 C for 24 h, cooled to 50 C and additional B (4.0 kg, 25 mol) was added slowly over 1 h in 1-kg portions, keeping temperature below 55 C. The reaction mixture was heated at 55 C for 24 h, concentrated under reduced pressure to a minimum volume (internal temp ~30 C, solution may occasionally foam), then diluted with isopropyl acetate (50 L) and washed with a saturated aqueous sodium sulfite solution (3 x 20 L) (final extract is pH ~ 8) followed by water (20 L). The organic layer was concentrated in vacuo to approximately 15 L then diluted with heptane (40 L). The resulting slurry was stirred for 24 h at ambient temperature. The solids were filtered, washed with heptane (10 L), and dried to give the title compound.

References: [1]Patent: WO2014/89324,2014,A1 .Location in patent: Paragraph 0284.
[2]Patent: CN104016979,2017,B .Location in patent: Paragraph 0800; 0801; 0802; 0803.
[3]Patent: US2012/122899,2012,A1 .Location in patent: Page/Page column 18.
[4]Patent: WO2012/129013,2012,A1 .Location in patent: Page/Page column 29-30.
[5]Patent: WO2013/169563,2013,A1 .Location in patent: Page/Page column 69; 70.
[6]Patent: WO2013/169574,2013,A2 .Location in patent: Page/Page column 65; 66.

2
[ 521980-82-5 ]
[ 1375541-21-1 ]

References: [1]Patent: US2012/122899,2012,A1 .
[2]Patent: WO2013/169563,2013,A1 .

3
[ 521980-82-5 ]
[ 1374248-79-9 ]

References: [1]Patent: US2012/122899,2012,A1 .

4
[ 521980-82-5 ]
[ 1374248-80-2 ]

References: [1]Patent: US2012/122899,2012,A1 .

5
[ 521980-82-5 ]
(6S)-N-[(3S,5S,6R)-6-Methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-3-carboxamide dihydrochloride [ No CAS ]

References: [1]Patent: US2012/122899,2012,A1 .

6
[ 521980-82-5 ]
(6S)-N-[(3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl]-2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-3-carboxamide [ No CAS ]

References: [1]Patent: US2012/122899,2012,A1 .

7
[ 521980-82-5 ]
[ 1356108-96-7 ]

Yield	Reaction Conditions	Operation in experiment
		Step B: (5-Bromopyridine-2,3-diyl)dimethanol; Sodium borohydride (15.9 g, 420 mmol) was added portionwise over 30 min to a solution of <strong>[521980-82-5]dimethyl 5-bromopyridine-2,3-dicarboxylate</strong> (20 g, 73 mmol) in ethanol (460 mL) precooled to 0 C. A solution of calcium chloride (23.3 g, 209 mmol) in 150 mL was added slowly at 0 C., and the reaction mixture was warmed to 23 C. and stirred overnight. Excess sodium borohydride was quenched by slow addition of aqueous 2 N HCl solution (230 mL, 460 mmol), followed by a stirring at 23 C. for 2 h. The mixture was concentrated to dryness. Saturated aqueous sodium bicarbonate solution was added to the residue until a pH of approximately 7 was reached. The aqueous mixture was extracted with 2-methyltetrahydrofuran (4×200 mL). The combined organic layers were dried over sodium sulfate then treated with a solution of 4 N HCl in dioxane (25 mL, 100 mmol). The resulting solid was filtered, washed with 2-methyltetrahydrofuran, and dried to give the title compound as a hydrochloride salt. MS: m/z=218.1 (M+1).
		Step B: (5-Bromopyridine-2,3-diyl)dimethanol; Sodium borohydride (15.9 g, 420 mmol) was added portionwise over 30 minutes to a solution of <strong>[521980-82-5]dimethyl 5-bromopyridine-2,3-dicarboxylate</strong> (20 g, 73 mmol) in ethanol (460 mL) precooled to 0 C. A solution of calcium chloride (23.3 g, 209 mmol) in ethanol (150 mL) was added slowly at 0 C, and the reaction mixture was warmed to 23 C and stirred overnight. Excess sodium borohydride was quenched by slow addition of aqueous 2 N HC1 solution (230 mL, 460 mmol), followed by a stirring at 23 C for 2 h. The mixture was concentrated to dryness. Saturated aqueous sodium bicarbonate solution was added to the residue until a pH of approximately 7 was reached. The aqueous mixture was extracted with 2-methyltetrahydrofuran (4 x 200 mL). The combined organic layers were dried over sodium sulfate then treated with a solution of 4 N HC1 in dioxane (25 mL, 100 mmol). The resulting solid was filtered, washed with 2-methyltetrahydrofuran, and dried to give the title compound as a hydrochloride salt. MS: mfz = 218.1 (M + 1).
		Step B: (5-Bromopyridine-2,3-diyl)dimethanol Sodium borohydride (15.9g, 420 mmol) was added portionwise over 30 min to a solution of <strong>[521980-82-5]dimethyl 5-bromopyridine-2,3-dicarboxylate</strong> (20 g, 73 mmol) in ethanol (460 mL) precooled to 0 C. A solution of calcium chloride (23.3 g, 209 mmol) in 150 mL was added slowly at 0 C, and the reaction mixture was warmed to 23 C and stirred overnight. Excess sodium borohydride was quenched by slow addition of aqueous 2 N HC1 solution (230 mL, 460 mmol), followed by a stirring at 23 C for 2 h. The mixture was concentrated to dryness. Saturated aqueous sodium bicarbonate solution was added to the residue until a pH of approximately 7 was reached. The aqueous mixture was extracted with 2-methyltetrahydrofuran (4 x 200 mL). The combined organic layers were dried over sodium sulfate then treated with a solution of 4 N HC1 in dioxane (25 mL, 100 mmol). The resulting solid was filtered, washed with 2-methyltetrahydrofuran, and dried to give the title compound as a hydrochloride salt. MS: mlz = 218.1 (M + 1).

Step B: (5-Bromopyridine-2,3-diyl)dimethanol Sodium borohydride (15.9 g, 420 mmol) was added portionwise over 30 min to a solution of <strong>[521980-82-5]dimethyl 5-bromopyridine-2,3-dicarboxylate</strong> (20 g, 73 mmol) in EtOH (460 mL) precooled to 0 C. A solution of calcium chloride (23.3 g, 209 mmol) in 150 mL was added slowly at 0 C, and the reaction mixture was warmed to ambient temperature and stirred for 18 h. Excess sodium borohydride was quenched by slow addition of aqueous 2 N HC1 solution (230 mL, 460 mmol), followed by a stirring at ambient temperature for 2 h. The mixture was concentrated to dryness in vacuo. Saturated aqueous sodium bicarbonate solution was added to the residue until a pH of approximately 7 was reached. The aqueous mixture was extracted with 2-methyltetrahydrofuran (4 x 200 mL). The combined organic layers were dried over sodium sulfate then treated with a solution of 4 N HC1 in dioxane (25 mL, 100 mmol). The resulting solid was filtered, washed with 2-methyltetrahydrofuran, and dried to give the title compound as a hydrochloride salt. MS: mlz = 218.1 (M + 1).

References: [1]Patent: US2012/122899,2012,A1 .Location in patent: Page/Page column 18.
[2]Patent: WO2012/129013,2012,A1 .Location in patent: Page/Page column 30.
[3]Patent: WO2013/169563,2013,A1 .Location in patent: Page/Page column 70.
[4]Patent: WO2013/169574,2013,A2 .Location in patent: Page/Page column 66.
[5]Drugs of the Future,2019,vol. 44,p. 869 - 879.

8
[ 521980-82-5 ]
[ 1375541-27-7 ]

References: [1]Patent: US2012/122899,2012,A1 .
[2]Patent: WO2013/169563,2013,A1 .
[3]Patent: WO2013/169574,2013,A2 .
[4]Drugs of the Future,2019,vol. 44,p. 869 - 879.

9
[ 521980-82-5 ]
[ 1318253-26-7 ]

References: [1]Patent: US2012/122899,2012,A1 .
[2]Patent: WO2013/169563,2013,A1 .
[3]Patent: WO2013/169574,2013,A2 .
[4]Drugs of the Future,2019,vol. 44,p. 869 - 879.

10
[ 521980-82-5 ]
[ 1375541-30-2 ]

References: [1]Patent: US2012/122899,2012,A1 .
[2]Patent: WO2013/169563,2013,A1 .
[3]Patent: WO2013/169574,2013,A2 .
[4]Drugs of the Future,2019,vol. 44,p. 869 - 879.

11
[ 521980-82-5 ]
methyl (6R)-2'-oxo-1'-[2-(trimethylsilyl)ethoxy]methyl}-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-3-carboxylate [ No CAS ]
[ 1375542-65-6 ]

References: [1]Patent: US2012/122899,2012,A1 .

12
[ 521980-82-5 ]
[ 1375541-45-9 ]

References: [1]Patent: US2012/122899,2012,A1 .
[2]Patent: WO2013/169563,2013,A1 .

13
[ 521980-82-5 ]
[ 1375541-47-1 ]

References: [1]Patent: US2012/122899,2012,A1 .
[2]Patent: WO2013/169563,2013,A1 .

14
[ 521980-82-5 ]
ethyl (6S)-5'-bromo-2’-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-3-carboxylate [ No CAS ]