Name: 945953-41-3|tert-Butyl 4-(2-oxoethyl)piperazine-1-carboxylate|97%
Brand: Ambeed
SKU: A507731
Price: 127.0 USD
Availability: InStock
Rating: 91 (32 reviews)

1
[ 77279-24-4 ]
[ 945953-41-3 ]

Yield	Reaction Conditions	Operation in experiment
		Oxalyl chloride (3.6 mL, 0.0425 mol) was dissolved in DCM (87 mL) at -78 C. Dimethyl sulfoxide (6.58 mL, 0.0927 mol) was added and the solution was held at -78 C for 10 min. To the resultant mixture was added a solution of tert-butyl 4-(2- hydroxyethyl)piperazine- 1 -carboxylate (from Oakwood, 8.90 g, 0.0386 mol) in DCM (44 mL) over 15 min. The reaction was stirred at -78 C for 1 h, then triethylamine (26.9 mL, 0.193 mol) was added. The mixture was warmed to RT over 30 minutes and then stirred at RT for another 30 min. The mixture was diluted with DCM, washed with water (2x), brine (l x), dried over sodium sulfate, and concentrated. The crude product (8.10 g, 91.8%) was used directly in next step without further purification. ChiEta NMR (400 MHz, CDC13): delta 9.70 (1H, s), 3.48 (4H, m), 3.19 (2H, s), 2.47 (4H, m), 1.45 (9H, s) ppm.
		[00107] Benzyloxycarbonyl (Boc) protected pperazne 9 was oxdzed togive aldehyde 10. Compound 12 was obtained by treaUng compound 12 w[thcompound 11 n the presence of sodium tracetoxyborohydrde (STAB) n DCM.
0.216 g		Oxalyl chloride (165 mg, 1.30 mmol) was dissolved in anhydrous methylene chloride (4 mL) Nitrogen was charged and cooled to -78 C. Dimethylsulfoxide (0.20 g, 2.60 mmol) was diluted in methylene chloride (1 mL) and slowly added, followed by stirring for 10 minutes. Compound 6-b (0.2 g, 0.87 mmol) was dissolved in methylene chloride (2 mL) And the mixture was slowly added thereto. The mixture was further stirred for 1 hour, Triethylamine (0.44 g, 4.34 mmol) was slowly added. The temperature was raised to room temperature and stirred for 3 hours. After completion of the reaction, distilled water (30 mL) was added and the mixture was extracted with methylene chloride. The organic layer was washed with distilled water and saturated brine, dried over anhydrous sodium sulfate and concentrated to give the title compound 6-c as a yellow liquid (0.216 g).

371 mg

To a stirred solution of oxalyl chloride (0.380 ml, 4.25 mmol) in anhydrous DCM (10 ml) at -78C was added DMSO (0.538 ml, 7.58 mmol). The RM was stirred for 30 min, followed by the addition of 1 -Boc-4-(2-hydroxyethyl)piperazine (500 mg, 2.106 mmol) in DCM (10 ml). After stirring the RM at -78C for 30 minutes, TEA (2.4 ml, 17.22 mmol) was added and stirring was continued for 1 .5 h while allowing the RM to warm to RT. The RM was quenched by addition of a sat. aq. solution of NaHC03and was then extracted with DCM. The combined organic phases were dried over Na2S04, evaporated to dryness and the residue was purified bychromatography on silica eluting with a mixture of EtOAc and MeOH (4:1) in EtOAc (from 0 to 30%) to afford the title compound as a solid (371 mg).1H NMR (400 MHz, DMSO -cfe) d 9.57 (d, J = 1 .5 Hz, 1 H), 3.31 (dd, J = 10.0, 5.0 Hz, 4H), 3.18 (d, J = 1 .5 Hz, 2H), 2.38 (t, J = 5.1 Hz, 4H), 1 .38 (s, 9H).

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 5826 - 5840
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 3242 - 3255
[3]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 3923 - 3933
[4]Patent: WO2011/28685,2011,A1 .Location in patent: Page/Page column 51
[5]Patent: WO2017/100703,2017,A1 .Location in patent: Paragraph 00106; 00107
[6]ACS Chemical Biology,2017,vol. 12,p. 163 - 173
[7]Patent: KR101798840,2017,B1 .Location in patent: Paragraph 0457-0458; 0467-0468
[8]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 446 - 451
[9]Patent: WO2019/186343,2019,A1 .Location in patent: Page/Page column 117; 118

2
[ 945953-41-3 ]
[ 16806-93-2 ]
1-[β-(4-oxo-4,5,6,7-tetrahydrobenzofuran-5-yliden)ethyl]-4-(tert-butoxycarbonyl)piperazine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3242 - 3255

3
[ 103-76-4 ]
[ 945953-41-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 90 percent / CHCl₃ / 24 h / 20 °C 2: 50 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -60 - 20 °C

Reference： [1]Dezi, Cristina; Brea, José; Alvarado, Mario; Raviña, Enrique; Masaguer, Christian F.; Loza, María Isabel; Sanz, Ferran; Pastor, Manuel [Journal of Medicinal Chemistry, 2007, vol. 50, # 14, p. 3242 - 3255]

4
[ 945953-41-3 ]
[ 945953-43-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: LDA; HMPA / tetrahydrofuran / 3 h / -78 °C 1.2: 49 percent / -78 - 20 °C 2.1: 94 percent / H₂ / Pd/C / tetrahydrofuran / 6 h / 20 °C

Reference： [1]Dezi, Cristina; Brea, José; Alvarado, Mario; Raviña, Enrique; Masaguer, Christian F.; Loza, María Isabel; Sanz, Ferran; Pastor, Manuel [Journal of Medicinal Chemistry, 2007, vol. 50, # 14, p. 3242 - 3255]

5
[ 945953-41-3 ]
[ 945953-44-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: LDA; HMPA / tetrahydrofuran / 3 h / -78 °C 1.2: 49 percent / -78 - 20 °C 2.1: 94 percent / H₂ / Pd/C / tetrahydrofuran / 6 h / 20 °C 3.1: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 5 h / 20 °C

Reference： [1]Dezi, Cristina; Brea, José; Alvarado, Mario; Raviña, Enrique; Masaguer, Christian F.; Loza, María Isabel; Sanz, Ferran; Pastor, Manuel [Journal of Medicinal Chemistry, 2007, vol. 50, # 14, p. 3242 - 3255]

6
[ 945953-41-3 ]
C₂₁H₂₃FN₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: LDA; HMPA / tetrahydrofuran / 3 h / -78 °C 1.2: 49 percent / -78 - 20 °C 2.1: 94 percent / H₂ / Pd/C / tetrahydrofuran / 6 h / 20 °C 3.1: 90 percent / trifluoroacetic acid / CH₂Cl₂ / 5 h / 20 °C 4.1: 78 percent / 1-hydroxybenzotriazole; dicyclohexylcarbodiimide / CH₂Cl₂ / 1 h / 0 - 5 °C

Reference： [1]Dezi, Cristina; Brea, José; Alvarado, Mario; Raviña, Enrique; Masaguer, Christian F.; Loza, María Isabel; Sanz, Ferran; Pastor, Manuel [Journal of Medicinal Chemistry, 2007, vol. 50, # 14, p. 3242 - 3255]

7
[ 24424-99-5 ]
[ 945953-41-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 90 percent / CHCl₃ / 24 h / 20 °C 2: 50 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -60 - 20 °C

Reference： [1]Dezi, Cristina; Brea, José; Alvarado, Mario; Raviña, Enrique; Masaguer, Christian F.; Loza, María Isabel; Sanz, Ferran; Pastor, Manuel [Journal of Medicinal Chemistry, 2007, vol. 50, # 14, p. 3242 - 3255]

8
[ 945953-41-3 ]
[ 101403-24-1 ]
[ 1171909-46-8 ]

Yield	Reaction Conditions	Operation in experiment
1.1 g	Stage #1: 4-(2-oxoethyl)piperazine-1-carboxylic acid tert-butyl ester; (S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride With acetic acid In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: With methanol; sodium cyanoborohydride In dichloromethane at 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Brown, Dennis A.; Mishra, Manoj; Zhang, Suhong; Biswas, Swati; Parrington, Ingrid; Antonio, Tamara; Reith, Maarten E.A.; Dutta, Aloke K. [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 11, p. 3923 - 3933]

9
[ 945953-41-3 ]
[ 2537-48-6 ]
[ 1270981-00-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: diethyl 1-cyanomethylphosphonate With potassium <i>tert</i>-butylate In tetrahydrofuran at 0 - 20℃; Stage #2: 4-(2-oxoethyl)piperazine-1-carboxylic acid tert-butyl ester In tetrahydrofuran at 0 - 20℃;	1.2 To a solution of 1 M of potassium tert-butoxide in THF (45.5 mL, 0.0455 mol) at 0 °C was added drop wise a solution of diethyl cyanomethylphosphonate (7.72 mL, 0.0477 mol) in THF (70 mL). The reaction mixture was warmed up to at RT, cooled to 0 °C again, and a solution of tert-butyl 4-(2-oxoethyl)piperazine-l-carboxylate (9.90 g, 0.0434 mol) in THF (10 mL) was added. The reaction mixture was allowed to warm up to RT and stirred for 2 more hours. After being quenched with water, the mixture was extracted with EtOAc. The organic layers were dried and concentrated. The residue was purified by silica gel column eluting with DCM to give the desired product (7.5 g, 69%).

Reference： [1]Current Patent Assignee: INCYTE CORP - WO2011/28685, 2011, A1 Location in patent: Page/Page column 52

10
[ 945953-41-3 ]
tert-butyl 4-{3-cyano-2-[4-(7-[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propyl}piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0 - 20 °C 1.2: 0 - 20 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: INCYTE CORP - WO2011/28685, 2011, A1

11
[ 945953-41-3 ]
[ 1171908-92-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: dichloromethane / 1 h / Inert atmosphere 1.2: 48 h / 20 °C / Inert atmosphere 2.1: hydrogen bromide / water / 12 h / 125 °C / Inert atmosphere