ChemicalBook Product Catalog Organic Chemistry Heterocyclic Compounds (S)-1-Boc-3-methylpiperazine

(S)-1-Boc-3-methylpiperazine

Product Name(S)-1-Boc-3-methylpiperazine
CAS147081-29-6
MFC10H20N2O2
MW200.28
EINECS206-459-5
MOL File147081-29-6.mol

Chemical Properties

Melting point	40-45 °C
alpha	-16 º (c=1 in dioxane)
Boiling point	268.7±15.0 °C(Predicted)
Density	0.997±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,2-8°C
form	Crystalline Powder
pka	8.52±0.40(Predicted)
color	White to yellow
optical activity	[α]/D -16±2°, c = 1 in dioxane
Sensitive	Air Sensitive
InChI	InChI=1S/C10H20N2O2/c1-8-7-12(6-5-11-8)9(13)14-10(2,3)4/h8,11H,5-7H2,1-4H3/t8-/m0/s1
InChIKey	FMLPQHJYUZTHQS-QMMMGPOBSA-N
SMILES	N1(C(OC(C)(C)C)=O)CCN[C@@H](C)C1
CAS DataBase Reference	147081-29-6(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	37/38-41-34
Safety Statements	26-39-45-36/37/39
RIDADR	3259
WGK Germany	3
F	10-34
HS Code	29335990
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Dam. 1 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

(S)-1-Boc-3-methylpiperazine is a hydrophobic compound that is structurally modified from the tetracyclic family of drugs. It has been shown to inhibit tumor cell growth by binding to the oncogene, KRASG12C, and downregulating its expression. This compound also inhibits cancer cell growth through the inhibition of the PI3K/AKT signaling pathway. The pharmacological effects of (S)-1-Boc-3-methylpiperazine are dependent on its ability to bind with high affinity to KRASG12C and inhibit its activity.

Chemical Properties

colorless to yellow liquid

Uses

Reactant involved in the synthesis of biologically activy molecules including:

CCR5 antagonists with anti-HIV-1 activity
Opioid receptor antagonists
Human growth hormone secretagogue receptor antagonists for treatment of obesity
Fatty acid oxidation inhibitors

Uses

(S)-4-Boc-2-methylpiperazine ((S)-1-Boc-3-methylpiperazine) is a reagent used in the synthesis of benzamide peptidomimetic as non-ATP competitive inihbitors.

Uses

Laboratory chemicals, Manufacture of substances.

Synthesis

24424-99-5

74879-18-8

147081-29-6

At 0 °C, (S)-2-methylpiperazine (400 mg) was dissolved in dichloromethane (20 mL) and di-tert-butyl dicarbonate (871 mg) was slowly added. The reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the reaction was quenched with deionized water (20 mL) followed by extraction with dichloromethane (2 x 40 mL). The organic phases were combined, washed with saturated sodium chloride solution (40 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford (S)-4-N-tert-butoxycarbonyl-2-methylpiperazine as a white solid (669 mg, 84% yield).

References

[1] Organic Process Research and Development, 2018, vol. 22, # 8, p. 978 - 990
[2] Patent: US2008/76758, 2008, A1. Location in patent: Page/Page column 88
[3] Patent: WO2008/70740, 2008, A1. Location in patent: Page/Page column 184
[4] Patent: US2005/261310, 2005, A1. Location in patent: Page/Page column 19
[5] Patent: WO2018/109050, 2018, A1. Location in patent: Paragraph 0226-0230; 0234-0236; 0240-0241

(S)-1-Boc-3-methylpiperazine

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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