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[ CAS No. 4023-02-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 4023-02-3
Chemical Structure| 4023-02-3
Structure of 4023-02-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4023-02-3 ]

CAS No. :4023-02-3 MDL No. :MFCD00210087
Formula : C4H7ClN4 Boiling Point : -
Linear Structure Formula :- InChI Key :RBZRMBCLZMEYEH-UHFFFAOYSA-N
M.W : 146.58 Pubchem ID :2734672
Synonyms :
1H-Pyrazole-1-carboximidamide hydrochloride

Calculated chemistry of [ 4023-02-3 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 36.75
TPSA : 67.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.43
Log Po/w (WLOGP) : 0.43
Log Po/w (MLOGP) : 0.01
Log Po/w (SILICOS-IT) : -0.72
Consensus Log Po/w : 0.03

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.36
Solubility : 6.33 mg/ml ; 0.0432 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 5.59 mg/ml ; 0.0381 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.08
Solubility : 122.0 mg/ml ; 0.83 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 4023-02-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4023-02-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 4023-02-3 ]
  • Downstream synthetic route of [ 4023-02-3 ]

[ 4023-02-3 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 288-13-1 ]
  • [ 420-04-2 ]
  • [ 4023-02-3 ]
YieldReaction ConditionsOperation in experiment
43% With hydrogenchloride In 1,4-dioxane for 1 h; Reflux Pyrazole (1.634 g, 24 mmol) and cyanamide (1 g, 24 mmol) were dissolved in 1,4-dioxane (24 mL), and 4M-HCl (6 mL) dissolved in 1,4- dioxane then stirred under reflux for 1 hour. After completion of the reaction, the reaction product was recrystallized in an ice water bath under the condition of diethyl ether. Yield 43percent
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 8, p. 2497 - 2502
[2] Organic Letters, 2004, vol. 6, # 26, p. 4925 - 4927
[3] Patent: KR101808950, 2017, B1, . Location in patent: Paragraph 0233-0236
[4] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 24, p. 2771 - 2774
[5] Journal of Medicinal Chemistry, 2005, vol. 48, # 3, p. 812 - 820
  • 2
  • [ 102-52-3 ]
  • [ 2582-30-1 ]
  • [ 4023-02-3 ]
Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 32, p. 11223 - 11233
  • 3
  • [ 420-04-2 ]
  • [ 35877-22-6 ]
  • [ 4023-02-3 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 51, p. 9423 - 9426
  • 4
  • [ 102-52-3 ]
  • [ 1937-19-5 ]
  • [ 4023-02-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 8168 - 8172
  • 5
  • [ 24424-99-5 ]
  • [ 4023-02-3 ]
  • [ 152120-61-1 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In water; acetone at 20℃; To a solution of di-tert-butyldicarbonate (13.4 g, 61.5 mmol) in acetone (45 mL) were added lH-pyrazole-l-carboxamidine hydrochloride (9.0 g, 61.5 mmol, 1.0 equiv.) and 9.0 mL of water. K2CO3 (4.24 g, 30.6 mmol, 0.5 equiv.) in H20 (12.0 mL) was added dropwise for 30 min at room temperature. After 2 h, another portion of di-tert- butyldicarbonate (1.35 g, 6 mmol, 0.1 equiv.) was added and the solution was stirred overnight. The acetone was removed under reduced pressure and the resulting white solid was dissolved in 30.0 mL of water, and allowed to stir at 0 °C for 30 min. The precipitated tert-butyl (imino(lH-pyrazol-l-yl)methyl)carbamate was collected by filtration, washed with water, washed with hexane, and dried in vacuo to provide the title compound as a colorless solid (11.37 g, 88percent yield). FontWeight="Bold" FontSize="10" H NMR (CDCI3, 400 MHz): δ 9.06 (brs, 1H), 8.45 (d, J= 3.2 Hz, 1H), 7.67 (d, J= 0.8 Hz, 1H), 7.59 (brs, 1H), 6.39 (dd, J = 2.8, 1.6 Hz, 1H), 1.54 (s, 9H).
74.8% With dmap; triethylamine In tetrahydrofuran at 20℃; for 20 h; Step 1:
Preparation of tert-butyl (1H-pyrazol-1-ylcarbonoimidoyl)carbamate
To a solution of (Boc)2O (61 g, 0.28 mol) in THF (1 L) was added DMAP (17 g, 0.14 mol) and Et3N (42 g, 0.42 mol).
After stirring for 30 min, 1H-pyrazole-1-carboximidamide hydrochloride (20 g, 0.14 mol) was added and the mixture was stirred at 20° C. for 20 hrs.
The reaction was then concentrated in vacuo and the residue was dissolved in EtOAc (500 mL).
The solution was washed with aq. NH4Cl (250 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo.
The residue was recrystallized from EtOAc (200 mL) to afford the title compound (22 g, 74.8percent yield) as white solid that was used as-is in the next step.
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 13, p. 2357 - 2359
[2] Organic and Biomolecular Chemistry, 2013, vol. 11, # 24, p. 3943 - 3948
[3] Patent: WO2015/147950, 2015, A2, . Location in patent: Page/Page column 38
[4] Patent: US2013/79324, 2013, A1, . Location in patent: Paragraph 0827; 0828
[5] Tetrahedron Letters, 1993, vol. 34, # 21, p. 3389 - 3392
[6] Tetrahedron, 2007, vol. 63, # 38, p. 9502 - 9513
[7] Patent: EP945138, 1999, A1,
  • 6
  • [ 501-53-1 ]
  • [ 4023-02-3 ]
  • [ 152120-62-2 ]
Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 21, p. 3389 - 3392
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 8168 - 8172
  • 7
  • [ 24424-99-5 ]
  • [ 4023-02-3 ]
  • [ 152120-61-1 ]
  • [ 152120-54-2 ]
YieldReaction ConditionsOperation in experiment
83.9% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2.66667 h; (Example 8)Synthesis of tert-butyl (tert-butoxycarbonyliminopyrazol- 1-yl-methyl)carbamate [compound (H)]Step F-I: N,N-dimethylformamide (350 ml) and N. N- diisopropyl ethylamine (125 ml) were added to tert- butyl( iminopyrazol-1-yl-methyl)carbamate lH-pyrazole-1- <n="80"/>carboxamidine hydrochloride (100 g) , and then a N.N- dimethylformamide (50 ml) solution of ditert-butyl dicarbonate (152 g) was added over 40 minutes at room temperature. After the mixture was stirred for 2 hours at the same temperature, water (500 ml) was added, the mixture was extracted with toluene (500 ml), and organic layer 1 and aqueous layer 1 were separated. Organic layer 1 was further washed twice with water (300 ml), and organic layer 2 was separated. Aqueous layer 1 was extracted with toluene (500 ml), and organic layer 3 was separated. Organic layer 2 and organic layer 3 were combined, and the solvent was distilled off under reduced pressure until the amount of the solution became approximately 300 ml. Hexane (500 ml) was added to the resulting solution at room temperature, the mixture was stirred for 30 minutes, followed by stirring for 30 minutes under ice-cooling, and then crystals were filtered. The crystals were washed with hexane (100 ml), and then dried under reduced pressure to give the title compound (120.3 g. 83.9percent yield) .
Reference: [1] Patent: WO2008/126943, 2008, A2, . Location in patent: Page/Page column 78-79
  • 8
  • [ 24424-99-5 ]
  • [ 4023-02-3 ]
  • [ 152120-54-2 ]
Reference: [1] Synthesis, 1994, # 6, p. 579 - 582
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