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[ CAS No. 915720-71-7 ]

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2D
Chemical Structure| 915720-71-7
Chemical Structure| 915720-71-7
Structure of 915720-71-7 *Storage: {[proInfo.prStorage]}

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Product Details of [ 915720-71-7 ]

CAS No. :915720-71-7MDL No. :MFCD29036411
Formula : C12H17BrN2O2 Boiling Point : 381.8±32.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :301.18Pubchem ID :90451672
Synonyms :

Computed Properties of [ 915720-71-7 ]

TPSA : 51.2 H-Bond Acceptor Count : 3
XLogP3 : 2.5 H-Bond Donor Count : 1
SP3 : 0.50 Rotatable Bond Count : 4

Safety of [ 915720-71-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 915720-71-7 ]

  • Upstream synthesis route of [ 915720-71-7 ]
  • Downstream synthetic route of [ 915720-71-7 ]

[ 915720-71-7 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
68.5% With triethylamine In dichloromethane at 20℃; for 16.00 h; Intermediate 61: (5)-tert-butyl (1 -(5-bromopyridi n-2-yl)ethyl)carbamate To a solution of (S)-1-(5-bromopyridin-2-yl)ethanamine (300 mg, 1.49 mmol) in DCM (7.5 mL)was added di-tert-butyl dicarbonate (358 mg, 1.64 mmol) and triethylamine (0.31 mL, 2.24mmol). The solution was stirred for 16 h at room temperature then washed with water andbrine. The organic layer was dried over Na2SO4, filtered and concentrated. Silica gel columnchromatography (EtOAc/heptane 0 to 80percent) provided a white solid (308 mg, 68.5percent yield).1H NMR (400 MHz, CDCI3) O 8.59 (d, J= 2.2 Hz, 1H), 7.76 (dd, J= 8.3, 2.4 Hz, 1H), 7.16 (d, J= 8.3 Hz, 1H), 5.57- 5.42 (m, 1H), 4.86- 4.73 (m, 1H), 1.43 (t, J= 3.4 Hz, 12H); MS m/z 303.4(M+H).
68.5% With triethylamine In dichloromethane at 20℃; for 16.00 h; To a solution of (S)-1-(5-bromopyridin-2-yl)ethanamine (300 mg, 1.49 mmol) in DCM (7.5 mL) was added di-tert-butyl dicarbonate (358 mg, 1.64 mmol) and triethylamine (0.31 mL, 2.24 mmol). The solution was stirred for 16 h at room temperature then washed with water and brine. The organic layer was dried over Na2504, filtered and concentrated. Silica gel column chromatography (EtOAc/heptane 0 to 80percent) provided a white solid (308 mg, 68.5percent yield).1H NMR (400 MHz, CDCI3) O 8.59 (d, J= 2.2 Hz, 1H), 7.76 (dd, J= 8.3, 2.4 Hz, 1H), 7.16 (d, J = 8.3 Hz, 1H), 5.57- 5.42 (m, 1H), 4.86- 4.73 (m, 1H), 1.43 (t, J= 3.4 Hz, 12H); MS m/z 303.4 (M+H).
Reference: [1] Patent: WO2014/141153, 2014, A1. Location in patent: Page/Page column 69; 70
[2] Patent: WO2014/141104, 2014, A1. Location in patent: Page/Page column 85
[3] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 10, p. 1116 - 1121
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YieldReaction ConditionsOperation in experiment
93%
Stage #1: With dmap In tetrahydrofuran at 50℃; for 20.00 h;
Stage #2: With lithium hydroxide; water In tetrahydrofuran at 20℃; for 20.00 h;
A solution of (S)-N-(l-(5-bromopyridin-2-yl)ethyl)acetamide (Method 28; 16.0 g, 65.82 mmol), DMAP (1.61 g, 13.16 mmol), and di-tert-butyl dicarbonate (28.73 g, 131.6 mmol) in THF (100 ml) was stirred at 50 °C for 20 hours. After cooled to room temperature, lithium hydroxide monohydrate (3.31 g, 78.98 mmol) and water (100 ml) were added. The reaction was stirred at room temperature for 20 hours and then diluted with ether (200 ml). The organic layer was separated, washed with brine (100 ml), and dried over sodium sulfate. After removal of solvent, the resulted residue was purified by column chromatography(hexane-EtOAc = 5:1) to give the title compound as a pale yellow oil (18.4 g, 93percent). 1H NMR (400 MHz) δ 8.60 (d, J= 2.0 Hz, IH), 8.01 (dd, J= 1.6 and 8.4 Hz, IH), 7.40 (d, J= 7.2 Hz , IH), 7.31 (d, J= 8.4 Hz, IH), 4.62 (m, IH), 1.37 (s, 9H), 1.31 (d, J= 7.2 Hz, 3H). MS: Calcd.: 300; Found: [M+H]+ 301.
Reference: [1] Patent: WO2006/123113, 2006, A2. Location in patent: Page/Page column 58
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Reference: [1] Patent: WO2006/123113, 2006, A2
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Reference: [1] Patent: WO2006/123113, 2006, A2
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