257937-08-9|tert-Butyl (3-bromopyridin-4-yl)carbamate| Ambeed

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Quality Control of [ 257937-08-9 ] Purity: 97% SDS Specification

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Product Details of [ 257937-08-9 ]

CAS No. :	257937-08-9
Formula :	C₁₀H₁₃BrN₂O₂
M.W :	273.13
SMILES Code :	C(C)(C)(C)OC(NC1=C(C=NC=C1)Br)=O
MDL No. :	MFCD01860257
InChI Key :	RPPLNTUECLIOOI-UHFFFAOYSA-N
Pubchem ID :	10707388

Safety of [ 257937-08-9 ]

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

Computational Chemistry of [ 257937-08-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.4
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	62.18
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	51.22 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.57
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	2.11
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.0
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.	1.54
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	1.82
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.21

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.89
Solubility	0.348 mg/ml ; 0.00127 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.	-2.82
Solubility	0.417 mg/ml ; 0.00153 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	-3.83
Solubility	0.0406 mg/ml ; 0.000149 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	Yes
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.	-6.47 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	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<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)	2.14

Application In Synthesis of [ 257937-08-9 ]

* 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 [ 257937-08-9 ]

[ 257937-08-9 ] Synthesis Path-Downstream 1~35

1
[ 98400-69-2 ]
[ 257937-08-9 ]

Yield	Reaction Conditions	Operation in experiment
52%		tert-Butyl (3-bromopyridin-4-yl)carbamate (3f) (52%) was prepared from pyridine 2f (2.70 g, 13.9 mmol) [34]. White solid; mp 91-92 C. 1H NMR (400 MHz, CDCl3) delta 8.58 (s, 1H), 8.37 (d, J=5.6 Hz, 1H), 8.15 (d, J=5.6 Hz, 1H), 7.18 (s, 1H), 1.55 (s, 9H); 13C NMR (101 MHz, CDCl3) delta 151.6, 151.4, 149.4, 143.1, 113.1, 109.6, 82.4, 28.1 (3C).

References: [1]Journal of Organic Chemistry,1999,vol. 64,p. 9430 - 9443.
[2]European Journal of Medicinal Chemistry,2015,vol. 102,p. 403 - 412.

2
[ 504-24-5 ]
6-(2,6-dichlorophenyl)-2-methanesulfinyl(or sulfonyl)-8-methyl-8H-pyrido<2,3-d>pyrimidin-7-one [ No CAS ]
[ 257937-08-9 ]

References: [1]Journal of Organic Chemistry,1999,vol. 64,p. 9430 - 9443.

3
[ 24424-99-5 ]
pentacarbonyl<1-<<(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl>oxy>-(E)-3-phenyl-2-propenylidene>chromium [ No CAS ]
[ 257937-08-9 ]

References: [1]Journal of Organic Chemistry,1999,vol. 64,p. 9430 - 9443.

4
[ 13534-98-0 ]
[ 24424-99-5 ]
[ 257937-08-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 48h;	tert-Butyl 3-bromopyridin-4-ylcarbamate To a solution of 4-amino-3-bromopyridine (1.0 g, 5.78 mmol) in THF (10 mL), DIPEA (1.1 mL, 6.36 mmol) and (Boc)20 (1.39 g, 6.36 mmol) were added. The reaction mixture was stirred at rt. for two days. It was then quenched with 1N HCl solution and extracted with ethyl acetate (2*50 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated to give tert-butyl 3-bromopyridin-4-ylcarbamate as a yellowish thick oil, (1.1 g, 70% yield). MS m/z 273,275(MH+); 1H NMR (300 MHz, CDCl3)delta ppm 1.51 (s, 9 H) 7.14 (s, 1 H) 8.12 (d, J=5.49 Hz, 1 H) 8.34 (d, J=5.86 Hz, 1 H) 8.55 (s, 1 H).
37 g	With triethylamine; In tetrahydrofuran; for 2h;	To stirred a solution of 4-amino 3-bromo pyridine (10.0 g, 57.803 mmol) in THF (500 ml) were added triethylamine (8.8 g, 86.705 mmol) and Boc anhydride (37.89 g, 173.410 mmol). The reaction mixture was stirred for 2 h, before pouring into water (700 ml) and extracted with EtOAc (500 ml x 2), yielding ie/f-butyl (3- bromopyridin-4-yl)carbamate (37.0 g, 136.029 mmol). MS: 274.95 (M+2).

References: [1]ChemCatChem,2019,vol. 11,p. 4154 - 4160.
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 11859 - 11862.
Angew. Chem.,2016,vol. 128,p. 12038 - 12041,4.
[3]Patent: US2006/46983,2006,A1 .Location in patent: Page/Page column 186.
[4]Patent: WO2018/69468,2018,A1 .Location in patent: Page/Page column 76.

5
[ 863579-14-0 ]
[ 257937-08-9 ]
[ 877281-08-8 ]

Yield	Reaction Conditions	Operation in experiment
38%	With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃;	Methyl 2-(4-(tert-butoxycarbonyl)pyridin-3-yl)-3-cyclohexyl-1H-indole-6-carboxylate To a mixture of methyl 3-cyclohexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-6-carboxylate (383 mg, 1.0 mmol), <strong>[257937-08-9]tert-butyl 3-bromopyridin-4-ylcarbamate</strong> (328 mg, 1.2 mmol) and LiCl (84.8 mg, 2.0 mmol), in ethanol (3 mL) and toluene (3 mL) was added, 2M aqueous Na2CO3 (1.25 mL, 2.5 mmol) solution. The mixture was then degassed by the application of vacuum followed by flushing with N2.Pd(PPh3)4 (58 mg, 0.05 mmol) was then added and the reaction was heated at 80 C. overnight. The resultant mixture was then filtered and concentrated under vacuum, and the product residue was purified by Prep. reverse phase HPLC to afford the title compound as an off-white solid, (170 mg, 38% yield). MS m/z 450(MH+); 1H NMR (300 MHz, CDCl3) delta ppm 1.15-1.33 (m, 13 H) 1.63-1.98 (m, 6 H) 2.45 (m, 1 H) 3.92 (s, 3 H) 6.94 (s, 1 H) 7.75-7.89 (m, 2 H) 8.17 (s, 1 H) 8.21 (d, J=5.86 Hz, 1 H) 8.37 (s, 1 H) 8.45 (d, J=5.86 Hz, 1 H) 9.45 (s, 1 H).

References: [1]Patent: US2006/46983,2006,A1 .Location in patent: Page/Page column 186-187.

6
[ 2917-46-6 ]
[ 257937-08-9 ]
[ 1622406-75-0 ]

References: [1]Chemistry - A European Journal,2014,vol. 20,p. 10131 - 10139.

7
[ 2917-46-6 ]
[ 257937-08-9 ]
[ 1622406-56-7 ]

References: [1]Chemistry - A European Journal,2014,vol. 20,p. 10131 - 10139.

8
[ 257937-08-9 ]
[ 1622406-69-2 ]

References: [1]Chemistry - A European Journal,2014,vol. 20,p. 10131 - 10139.
[2]Chemistry - A European Journal,2014,vol. 20,p. 10131 - 10139.

9
[ 257937-08-9 ]
[ 1622407-04-8 ]

References: [1]Chemistry - A European Journal,2014,vol. 20,p. 10131 - 10139.

10
[ 21581-91-9 ]
[ 257937-08-9 ]
[ 1622406-94-3 ]

References: [1]Chemistry - A European Journal,2014,vol. 20,p. 10131 - 10139.

11
[ 106-96-7 ]
[ 257937-08-9 ]
tert-butyl (3-bromopyridin-4-yl)(prop-2-yn-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium hydride; In N,N-dimethyl-formamide;	tert-Butyl (3-bromopyridin-4-yl)(prop-2-yn-1-yl)carbamate (4f) (69%) was prepared by alkylation of carbamate 3f (1.90 g, 6.95 mmol) with propargyl bromide [34] . It was obtained as a brown oil after chromatography on SiO2 (eluent, 1:1 petroleum ether/diethyl ether). 1H NMR (400 MHz, CDCl3) delta 8.80 (s, 1H), 8.55 (d, J = 5.1 Hz, 1H), 7.36 (bs, 1H), 4.71 (bs, 1H), 4.08 (bs, 1H), 2.25 (s, 1H), 1.43 (s, 9H); 13C NMR (101 MHz, CDCl3) delta 153.2, 152.6, 149.5, 147.8, 125.2, 121.7, 82.3, 78.5, 73.1, 37.8, 28.2 (3C).

References: [1]European Journal of Medicinal Chemistry,2015,vol. 102,p. 403 - 412.

12
[ 257937-08-9 ]
C₁₃H₁₆N₂O₂ [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 102,p. 403 - 412.

13
[ 257937-08-9 ]
tetraethyl (3-(pyrrolo[3,2-c]pyridin-3-yl)propane-1,1-diyl)bis(phosphonate) [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 102,p. 403 - 412.

14
[ 257937-08-9 ]
1-(tert-butoxycarbonyl)-3-[3,3-bis(diethoxyphosphoryl)propyl]-pyrrolo[3,2-c]pyridine [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 102,p. 403 - 412.

15
[ 536-74-3 ]
[ 257937-08-9 ]
(3-Phenylethynyl-pyridin-4-yl)-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11859 - 11862.
Angew. Chem.,2016,vol. 128,p. 12038 - 12041,4.

16
[ 257937-08-9 ]
[ 74-99-7 ]
[ 211029-71-9 ]

References: [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11859 - 11862.
Angew. Chem.,2016,vol. 128,p. 12038 - 12041,4.

17
[ 257937-08-9 ]
[ 211029-77-5 ]

References: [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11859 - 11862.
Angew. Chem.,2016,vol. 128,p. 12038 - 12041,4.

18
[ 257937-08-9 ]
2-phenylpyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11859 - 11862.
Angew. Chem.,2016,vol. 128,p. 12038 - 12041,4.

19
[ 257937-08-9 ]
(-)-tert-butyl 2-methyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11859 - 11862.
Angew. Chem.,2016,vol. 128,p. 12038 - 12041,4.

20
[ 257937-08-9 ]
(-)-tert-butyl 2-phenyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate [ No CAS ]
(+)-tert-butyl 2-phenyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11859 - 11862.
Angew. Chem.,2016,vol. 128,p. 12038 - 12041,4.

21
[ 2942-14-5 ]
[ 257937-08-9 ]
tert-butyl (3-(5-methoxybenzo[d]thiazol-2-yl)pyridin-4-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.5 g	With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; copper(I) bromide; In toluene; at 110℃; for 16h;	To a stirred solution of 5-methoxybenzo[d]thiazole (5 g, 30.299 mmol) and tert- butyl(3-bromopyridine-4-yl)carbamate (24.7 g, 90.802 mmol) in toluene was added K2C03. Cu(l)Br (1 .7 g, 1 1.846 mmol), Pd(OAc)2 (0.8 g, 3.563 mmol) and xantphose (3.5 g, 6.049 mmol) were added to the reaction mixture before heating to 1 10 C for 16 h. The resulting reaction mixture was poured in to water (500 ml) and extracted with EtOAc (500 ml). The resulting crude material was purified by column chromatography (20% EtOAc in Hexane) yielding ie f-butyl (3-(5- methoxybenzo[d]thiazole-2-yl) pyridine-4-yl) carbamate (PST-148) (2.5 g, 7.002 mmol). MS: ES+ 358 (M+1 ); 1 H NMR (400 MHz, DMSO-d6) delta ppm: 1 1 .68 (s, 1 H), 9.03 (s, 1 H), 8.54 (d, J = 5.6 Hz, 1 H), 8.30 (d, J = 5.6 Hz, 1 H), 8.10 (d, J = 9.2 Hz, 1 H), 7.50 (d, J = 2.4 Hz, 1 H), 7.20 (dd, J = 8.8, 2.4 Hz, 1 H), 3.90 (s, 3H), 1 .55 (s, 9H).

References: [1]Patent: WO2018/69468,2018,A1 .Location in patent: Page/Page column 76-77.

22
[ 257937-08-9 ]
3-(5-methoxybenzo[d]thiazol-2-yl)pyridin-4-amine [ No CAS ]

References: [1]Patent: WO2018/69468,2018,A1 .

23
[ 257937-08-9 ]
tert-butyl (2-((3-(5-methoxybenzo[d]thiazol-2-yl)pyridin-4-yl)amino)-2-oxoethyl)carbamate [ No CAS ]

References: [1]Patent: WO2018/69468,2018,A1 .

24
[ 257937-08-9 ]
N-(3-(5-methoxybenzo[d]thiazol-2-yl)pyridin-4-yl)methanesulfonamide [ No CAS ]

References: [1]Patent: WO2018/69468,2018,A1 .

25
[ 108-22-5 ]
[ 257937-08-9 ]
1-(4-((tert-butoxycarbonyl)amino)pyridin-3-yl)propan-2-yl acetate [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 15525 - 15534.

26
[ 257937-08-9 ]
C₁₉H₃₂N₂O₂Si₂ [ No CAS ]