ethyl 3,5-diaMino-1H-pyrazole-4-carboxylate Chemical Properties

Melting point:

189-190℃

Boiling point:

419.4±40.0 °C(Predicted)

Density 

1.418±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

14.26±0.50(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C6H10N4O2/c1-2-12-6(11)3-4(7)9-10-5(3)8/h2H2,1H3,(H5,7,8,9,10)

InChIKey

HRAWNPOJGRIJSB-UHFFFAOYSA-N

SMILES

N1C(N)=C(C(OCC)=O)C(N)=N1

ethyl 3,5-diaMino-1H-pyrazole-4-carboxylate Usage And Synthesis

Uses

Ethyl 3,5-diaMino-1H-pyrazole-4-carboxylate belongs to carboxylic acid ester derivatives, which can be used as pharmaceutical intermediates and used in medical experimental research.

Synthesis

General procedure for the synthesis of ethyl 3,5-diamino-1H-pyrazole-4-carboxylate from ethyl (Z)-3-amino-4,4,4-trichloro-2-cyano-but-2-enoate: hydrazine (2.19 mL, 70 mmol) was added to ethyl (Z)-3-amino-4,4,4-trichloro-2-cyano-but-2-enoate (15.0 g, 58 mmol) in DMF (50 mL) solution. The reaction mixture was heated to 100 °C and kept for 1 h, followed by cooling to room temperature. The DMF was removed under vacuum and the residue was slurried in a 95:5 (v/v) mixture of DCM and 2 M methanol ammonia solution. The resulting precipitate was collected by filtration, washed with a 95:5 mixture of DCM:MeOH and dried under vacuum to afford 5.72 g (58% yield) of ethyl 3,5-diamino-1H-pyrazole-4-carboxylate as a white solid.1H NMR (400 MHz, DMSO) δ 10.53 (s, 1H), 5.28 (br, 4H), 4.14 (q, J = 7.1 Hz, 2H), 1.33-1.15 (t, J = 7.1 Hz, 3H).

References

[1] Patent: WO2015/73267, 2015, A1. Location in patent: Paragraph 317; 367
[2] Patent: CN104650092, 2017, B. Location in patent: Paragraph 0463-0464; 0469-0470
[3] Patent: CN108003161, 2018, A. Location in patent: Paragraph 0849; 0855-0857
[4] Patent: WO2011/3065, 2011, A2. Location in patent: Page/Page column 110

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