N,N'-BIS-BOC-1-GUANYLPYRAZOLE Chemical Properties

Melting point:

86-90 °C(lit.)

Density 

1.16±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slghtly), Methanol (Slightly)

form 

Solid

pka

6.92±0.46(Predicted)

color 

White to Off-White

Water Solubility 

Slightly soluble in water. Soluble in methanol, and chloroform.

InChI

InChI=1S/C14H22N4O4/c1-13(2,3)21-11(19)16-10(18-9-7-8-15-18)17-12(20)22-14(4,5)6/h7-9H,1-6H3,(H,16,17,19,20)

InChIKey

QFNFDHNZVTWZED-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)/N=C(/NC(OC(C)(C)C)=O)\N1C=CC=N1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29331990

N,N'-BIS-BOC-1-GUANYLPYRAZOLE Usage And Synthesis

Uses

N,N'-Di-Boc-1H-pyrazole-1-carboxamidine is used in the stereoselective synthesis of the bicyclic guanidine alkaloid (+)-monanchorin.N,N'-Di-Boc-1H-pyrazole-1-carboxamidine (also known as Bis-Boc-pyrazolocarboxamidine,Pyrazol(BOC)2) is typically used as a guanidinylating reagent in organic synthesis.

Chemical Properties

White solid

Uses

N,N'-Di-Boc-1H-pyrazole-1-carboxamidine is used in the stereoselective synthesis of the bicyclic guanidine alkaloid (+)-monanchorin.

Synthesis

Step F-2: Synthesis of tert-butyl (tert-butoxycarbonyliminopyrazol-1-yl - methyl) carbamate [Compound (H) N-Boc-1H-pyrazole-1-carboxamidine (50 g) prepared in step BI was dissolved in tetrahydrofuran (100 ml) and slowly added to a suspension of 60% sodium hydride (9.99 g) in tetrahydrofuran (100 ml) over a period of 1 h. The temperature of the reaction was maintained at -5°C to 0°C. After 30 minutes of continuous stirring at this temperature, a solution of tetrahydrofuran (100 ml) of di-tert-butyl dicarbonate (57.1 g) was added dropwise, keeping the temperature constant. Subsequently tetrahydrofuran (250 ml) was added and the reaction mixture was heated and stirred at reflux for 2 hours. After completion of the reaction, it was cooled to room temperature, the reaction was quenched by the addition of acetic acid (20.4 ml) and concentrated under reduced pressure to about 150 ml. 5% aqueous sodium bicarbonate solution (500 ml) was added to the concentrate and extracted with ethyl acetate (500 ml). The organic layer was washed with water (150 ml) and concentrated under reduced pressure to about 75 ml. Hexane (200 ml) was added to the residue and inoculated with crystals, which were stirred under cooling in an ice bath for 40 min. The crystals were collected by filtration, washed with hexane (50 ml) and dried under reduced pressure to give N,N'-di-BOC-1H-1 -guanidinopyrazole (54.47 g, 73.8% yield). 1H NMR (CDCl3, 500MHz): δ 1.49 (9H, s), 1.55 (9H, s), 6.41 (1H, dd, J = 1.5, 2.7Hz), 7.62 (1H, dd, J = 0.7, 1.5Hz), 8.30 (1H, dd, J = 0.7, 2.7Hz), 8.93 (1H, brs). 13C NMR (CDCl3, 125MHz): δ 28.1, 28.2, 81.4, 83.4, 109.8, 129.0, 139.2, 142.8, 149.4, 157.4.

References

[1] Patent: WO2008/126943, 2008, A2. Location in patent: Page/Page column 79-80
[2] Synthesis, 2004, # 10, p. 1655 - 1663
[3] Tetrahedron Letters, 1993, vol. 34, # 21, p. 3389 - 3392
[4] Synthetic Communications, 1993, vol. 23, # 21, p. 3055 - 3060

N,N'-BIS-BOC-1-GUANYLPYRAZOLE(152120-54-2)Related Product Information

• Aminoguanidine Sulfate
• tert-butyl ((1R,2R)-2-(hydroxymethyl)cyclopentyl)carbamate
• (1R,2R)-trans-N-Boc-2-Aminocyclohexanol
• tert-butyl ((1R,2S)-2-(aminomethyl)cyclopentyl)carbamate
• N,N'-BIS(TERT-BUTOXYCARBONYL)-N-BENZYL-1H-PYRAZOLE-1-CARBOXAMIDINE
• N,N'-BIS(TERT-BUTOXYCARBONYL)-N-(3-PICOLYL)-1H-PYRAZOLE-1-CARBOXAMIDINE
• N,N'-BIS-BOC-1-GUANYLPYRAZOLE
• N,N'-BIS(TERT-BUTOXYCARBONYL)-N-TETRAHYDROFURFURYL-1H-PYRAZOLE-1-CARBOXAMIDINE