1152093-60-1|tert-Butyl 4-(6-bromopyridin-2-yl)-1,4-diazepane-1-carboxylate| Ambeed

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Quality Control of [ 1152093-60-1 ] Purity: 95% SDS Specification

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Product Details of [ 1152093-60-1 ]

CAS No. :	1152093-60-1
Formula :	C₁₅H₂₂BrN₃O₂
M.W :	356.26
SMILES Code :	CC(C)(C)OC(=O)N1CCCN(CC1)C1=NC(Br)=CC=C1
MDL No. :	MFCD22373438

Safety of [ 1152093-60-1 ]

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

Application In Synthesis of [ 1152093-60-1 ]

* 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 [ 1152093-60-1 ]

[ 1152093-60-1 ] Synthesis Path-Downstream 1~24

1
[ 1042986-01-5 ]
[ 1152093-60-1 ]
[ 1042986-02-6 ]

Yield	Reaction Conditions	Operation in experiment
87%		Intermediate 10:tert-butyl 4-(6-(2-fluoro-5-methylnicotinoyl)pyridin-2-yl)-l,4-diazepane-l-carboxylate [00369] To a solution of tert-butyl 4-(6-bromopyridin-2-yl)- 1 ,4-diazepane- 1 -carboxylate (898 mg, 2.52 mmol) in tetrahydrofuran (10 ml) at -78C was added a 2.5M solution of "butyllithium in hexanes (1.01 ml, 2.52 mmol) dropwise maintaining the temperature at -78C. After complete addition, the solution was stirred at -78C for a further 20 minutes. A solution of 2-fluoro-N-methoxy-N,5-dimethylnicotinamide (500 mg, 2.52 mmol) in tetrahydrofuran (5 ml)was added dropwise at -78C and the reaction mixture was stirred at -78C for 1 hour. The reaction was quenched with a saturated solution of ammonium chloride. The mixture was stirred at room temperature for 20 minutes and extracted into ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography (ISCO Companion D, 4Og column, 0- 20% EtO Ac/Petrol) to afford the title compound as a sticky green oil (906 mg, 87% yield). <n="174"/>[00370] 1H NMR (DMSO-(I6, 400 MHz) delta 1.18 and 1.27 (9H, 2s, rotamers), 1.58-1.73 (2H, m), 2.35 (3H, s), 3.15-3.63 (8H, m), 7.01 (IH, d), 7.31 (IH, dd), 7.74 (IH, m), 8.00 (IH, dd), 8.24 (IH, s); MS (ES+) 415.

References: [1]Patent: WO2008/94992,2008,A2 .Location in patent: Page/Page column 172-173.

3
[ 1206979-33-0 ]
[ 1152093-60-1 ]
[ 1527525-00-3 ]

Yield	Reaction Conditions	Operation in experiment
57%	With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 100℃; for 3h;	To a mixture of <strong>[1152093-60-1]tert-butyl 4-(6-bromopyridin-2-yl)-1,4-diazepane-1-carboxylate</strong> (2.55 g, 7.16 mmol) and 6-chloro-1H-pyrazolo[4,3-c]pyridine (1.0 g, 6.51 mmol) in 1,4-dioxane (20 mL) was added Cul (494 mg, 2.6 mmol), K2CO3 (3.6 g, 26 mmol), and diamine (460 mg, 5.2 mmol). The mixture was heated at 100 C for 3 hours, which was monitored by LCMS. After completion of the reaction, it was concentrated under reduced pressure. The crude was purified by silica gel chromatography using petroleum ether/EtOAc (2/1) as eluting solvents to afford tert-butyl 4-(6-(6-chloro-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate as a yellow solid (1.6 g, 57%). MS (ESI) m/z: 429 [M+H] +.

References: [1]Patent: WO2014/1377,2014,A1 .Location in patent: Page/Page column 103; 104; 151.

4
[ 144100-07-2 ]
[ 112275-50-0 ]
[ 1152093-60-1 ]

Yield	Reaction Conditions	Operation in experiment
50%	With N-ethyl-N,N-diisopropylamine; In ethanol; at 100℃; for 16h;	A mixture of 2-bromo-6-fluoropyridine (500 mg, 2.8 mmol), tert-butyl 1,4-diazepane-1-carboxylate (568 mg, 2.8 mmol) in DIPEA (1.83 g, 14.2 mmol) in ethanol (10 mL) was heated at 100 C for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue was diluted with EtOAc (100 mL). The solution was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford tert-butyl 4-(6-bromopyridin-2-yl)-1,4-diazepane-1-carboxylate as a colorless oil (500 mg, 50%). MS (ESI) m/z: 356 [M+H] +.

References: [1]Patent: WO2014/1377,2014,A1 .Location in patent: Page/Page column 103.
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 4458 - 4473.

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[ 1152093-60-1 ]
[ 1527523-74-5 ]