Methyl 3-amino-6-bromopyrazine-2-carboxylate Chemical Properties

Melting point:

164-166?C

Boiling point:

322.4±37.0 °C(Predicted)

Density 

1.754±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Chloroform, Ethyl Acetate, Methanol

pka

-1.74±0.10(Predicted)

form 

Solid

color 

Off-white to yellow

InChI

InChI=1S/C6H6BrN3O2/c1-12-6(11)4-5(8)9-2-3(7)10-4/h2H,1H3,(H2,8,9)

InChIKey

CNXSIRHOIFRMOB-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC(Br)=CN=C1N

CAS DataBase Reference

6966-01-4

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

37

HS Code 

2933998090

Methyl 3-amino-6-bromopyrazine-2-carboxylate Usage And Synthesis

Chemical Properties

Orange Solid

Uses

Pyrazine derivatives as Axl and C-Met receptor enzyme inhibitors.

Synthesis

General Steps: Example 1; Synthesis of 3-methyl-6-(4-(methylsulfonyl)phenyl)-N-phenylpiperazine-2-carboxamide (Compound IV-1) Method A: Step 1: Preparation of methyl 3-amino-6-bromopyrazine-2-carboxylate[A Methyl 3-aminopyrazine-2-carboxylate (8.35 g, 54.53 mmol) was mixed with N-bromosuccinimide (9.705 g, 54.53 mmol) in acetonitrile (100 mL), and the reaction was stirred for 16 hours at room temperature. After completion of the reaction, the precipitate was collected by filtration, washed with acetonitrile and dried to afford the target product methyl 3-amino-6-bromopyrazine-2-carboxylate as a yellow solid (11.68 g, 92% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 3.85 (s, 3H), 7.55 (br s, 2H), 8.42 (s, 1H) ppm; MS (ES+) m/z 233.

References

[1] Patent: WO2007/61360, 2007, A2. Location in patent: Page/Page column 71
[2] Heterocycles, 2005, vol. 65, # 10, p. 2321 - 2327
[3] Patent: WO2004/92177, 2004, A1. Location in patent: Page 35-36
[4] Patent: US2011/59118, 2011, A1. Location in patent: Page/Page column 84-85
[5] Patent: WO2010/54398, 2010, A1. Location in patent: Page/Page column 90

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