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[ CAS No. 883984-95-0 ]

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2D
Chemical Structure| 883984-95-0
Chemical Structure| 883984-95-0
Structure of 883984-95-0 *Storage: {[proInfo.prStorage]}

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Product Details of [ 883984-95-0 ]

CAS No. :883984-95-0MDL No. :MFCD19703288
Formula : C19H18ClN3O4 Boiling Point : 526.5±50.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :387.82Pubchem ID :59165781
Synonyms :

Computed Properties of [ 883984-95-0 ]

TPSA : 80.8 H-Bond Acceptor Count : 5
XLogP3 : 3 H-Bond Donor Count : 1
SP3 : 0.32 Rotatable Bond Count : 3

Safety of [ 883984-95-0 ]

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

Application In Synthesis of [ 883984-95-0 ]

  • Upstream synthesis route of [ 883984-95-0 ]
  • Downstream synthetic route of [ 883984-95-0 ]

[ 883984-95-0 ] Synthesis Path-Upstream   1~3

  • 1
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YieldReaction ConditionsOperation in experiment
54%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 2.83 h; Inert atmosphere
Stage #2: at -78 - 40℃; Inert atmosphere
Stage #3: With water; sodium hydrogencarbonate In tetrahydrofuran
Step 2:
benzyl 7'-chloro-2'-oxo-1',2'-dihydrospiro[piperidine-4,4'-pyrido[2,3d][1,3]-oxazin]-1-carboxylate
Under a nitrogen atmosphere 26 mL (1734 mmol) N,N,N,N-tetramethylenethylenediamine in 180 mL THF were cooled to -20° C. and 70 mL (175 mmol) of a 2.5 molar butyllithium solution were added within 10 min.
After 30 minutes' stirring the reaction mixture was cooled to -78° C. and at this temperature 17.8 g (78.0 mmol) tert-butyl (6-chloro-pyridin-2-yl)-carbamate in 120 mL THF were added dropwise within 20 min.
The reaction mixture was stirred for 2.5 h at -78° C. and then 27.2 g (116.7 mmol) benzyl 4-oxo-piperidine-1-carboxylate in 60 mL THF were added within 10 min.
After another hour's stirring at -78° C. the reaction mixture was first of all heated to RT and then stirred for 18 h at 40° C.
Then the reaction mixture was decomposed by the dropwise addition of 150 mL saturated sodium hydrogen carbonate solution.
Then the reaction mixture was extracted several times with DCM.
The combined organic phases were washed with water, dried and evaporated down.
The residue was triturated with PE/EtOAc 1/1, the precipitate formed was suction filtered, washed with PE/ETOAc 1/1 and dried.
Yield: 16.4 g (54percent of theoretical)
ESI-MS: m/z=388 (M+H)+
Rt(HPLC): 1.57 min (method C)
54%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 2.50 h; Inert atmosphere
Stage #2: at -78 - 40℃; for 19.00 h;
Step 2: benzyl-7'-chloro-2'-oxo-1',2'-dihydrospiro[piperidin-4,4'-pyrido[2,3d][1,3]oxazin]-1-carboxylate; Under a nitrogen atmosphere 26.0 mL (173 mmol) N,N,N,N-tetramethylene-ethylenediamine in 180 mL THF were cooled to -20° C. and combined with 70.0 mL (175 mmol) 2.5 M butyllithium solution. After 30 minutes' stirring the reaction mixture was cooled to -78° C., and at this temperature 17.8 g (78.0 mmol) tert-butyl (6-chloro-pyridin-2-yl)-carbamate in 120 mL THF were slowly added dropwise. The reaction mixture was stirred for 2.5 h at -78° C. and then combined with 27.2 g (117 mmol) Cbz-protected piperidone in 60 mL of THF. After one hour at -78° C. the mixture was heated to RT and then stirred for 18 h at 40° C. The reaction mixture was decomposed by the dropwise addition of 150 mL saturated sodium hydrogen carbonate solution. Then it was extracted with DCM. The combined organic phases were washed with water, dried and evaporated down. The residue was triturated with PE/EtOAc (1/1), the precipitate formed was suction filtered, washed with PE/EtOAc (1/1) and dried.Yield: 16.4 g (54percent of theoretical)ESI-MS: m/z=388 (M+H)+ Rt(HPLC): 1.57 min (method B)
54% With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78 - 40℃; Inert atmosphere Step 2: benzyl 7'-chloro-2'-oxo-1',2'-dihydrospiro[piperidine-4,4'-pyrido[2,3d]-[1,3]oxazine]-1-carboxylate Under a nitrogen atmosphere 26 mL (173.39 mmol) N,N,N,N-tetramethylenethylene-diamine in 180 mL THF were cooled to -20° C. and within 10 min 70 mL (175 mmol) of a 2.5 molar butyllithium solution were added. After 30 minutes' stirring the reaction mixture was cooled to -78° C. and at this temperature 17.84 g (78.00 mmol) tert-butyl (6-chloro-pyridin-2-yl)-carbamate in 120 mL THF were added dropwise within 20 min. The reaction mixture was stirred for 2.5 h at -78° C. and then combined with 27.22 g (116.70 mmol) Z-piperidone in 60 mL THF within 10 min. After a further hour's stirring at -78° C. the reaction mixture was first of all heated to RT and then stirred for 18 h at 40° C. Then the reaction mixture was decomposed by the dropwise addition of 150 mL saturated sodium hydrogen carbonate solution. Then the reaction mixture was extracted several times extracted with DCM. The combined organic phases were washed with water, dried and evaporated down. The residue was triturated with PE/EtOAc 1/1, the precipitate formed was suction filtered, washed with PE/ETOAc 1/1 and dried.Yield: 16.40 g (54percent of theoretical)ESI-MS: m/z=388 (M+H)+ Rt(HPLC): 1.57 min (method C)
Reference: [1] Patent: US2011/21500, 2011, A1. Location in patent: Page/Page column 45-46
[2] Patent: US2011/172218, 2011, A1. Location in patent: Page/Page column 29-30
[3] Patent: US2012/149698, 2012, A1. Location in patent: Page/Page column 26
[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 22, p. 6368 - 6372
[5] Patent: WO2006/41830, 2006, A2. Location in patent: Page/Page column 55
[6] Patent: WO2006/44504, 2006, A1. Location in patent: Page/Page column 79
[7] Patent: WO2006/99268, 2006, A2. Location in patent: Page/Page column 65-66
[8] Patent: US2018/50992, 2018, A1. Location in patent: Paragraph 1392
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Reference: [1] Patent: WO2007/16087, 2007, A2. Location in patent: Page/Page column 49; 66
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Reference: [1] Patent: US2011/172218, 2011, A1
[2] Patent: US2012/149698, 2012, A1
[3] Patent: US2018/50992, 2018, A1
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