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[ CAS No. 6994-25-8 ] {[proInfo.proName]}

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Chemical Structure| 6994-25-8
Chemical Structure| 6994-25-8
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Product Details of [ 6994-25-8 ]

CAS No. :6994-25-8 MDL No. :MFCD00005238
Formula : C6H9N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :YPXGHKWOJXQLQU-UHFFFAOYSA-N
M.W : 155.15 Pubchem ID :81472
Synonyms :
3-Amino-4-ethoxycarbonylpyrazole

Calculated chemistry of [ 6994-25-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 39.08
TPSA : 81.0 ?2

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) : -6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.96
Log Po/w (XLOGP3) : 0.64
Log Po/w (WLOGP) : 0.18
Log Po/w (MLOGP) : -0.18
Log Po/w (SILICOS-IT) : 0.39
Consensus Log Po/w : 0.4

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.34
Solubility : 7.03 mg/ml ; 0.0453 mol/l
Class : Very soluble
Log S (Ali) : -1.92
Solubility : 1.88 mg/ml ; 0.0121 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.34
Solubility : 7.04 mg/ml ; 0.0454 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.71

Safety of [ 6994-25-8 ]

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 [ 6994-25-8 ]

* 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 [ 6994-25-8 ]
  • Downstream synthetic route of [ 6994-25-8 ]

[ 6994-25-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 6994-25-8 ]
  • [ 1353100-91-0 ]
YieldReaction ConditionsOperation in experiment
100% With copper(ll) bromide; isopentyl nitrite In acetonitrile at 50℃; To a 0° C. solution of ethyl 3-amino-1H-pyrazole-4-carboxylate (5.0 g, 32 mmol) and copper (II) bromide (7.2 g, 32 mmol) in acetonitrile (65 mL) was slowly added isoamyl nitrite (12 mL, 86 mmol). The reaction was heated to 50° C. and stirred overnight. The reaction was cooled to room temperature and quenched with 1 N aqueous hydrochloric acid (150 mL). The mixture was extracted with ethyl acetate (3.x.100 mL). The combined organics were washed with water, dried over sodium sulfate, filtered, and concentrated to give the title compound as a brown oil that partially solidified under vacuum overnight (7.1 g, 100percent). 1H NMR (400 MHz, CDCl3, δ): 9.78 (br. s., 1H), 8.10 (br. s., 1H), 4.33 (q, J=7.22 Hz, 2H), 1.36 (m, 3H).
81% With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 20 - 70℃; for 3 h; Inert atmosphere To a solution of terf-BuONO (156 mmol, 16.5 g) in acetonitrile (300 mL) was added CuBr2 (156 mmol, 34.8 g). After the mixture was stirred at rt for 1 h under nitrogen, ethyl 3-amino-lH-pyrazole-4-carboxylate ( 129 mmol, 20.0 g) was added portionwise over 30 min. The reaction mixture was stirred at rt for 30 min and then was allowed to warm up to 70°C and was stirred for another 2 h. After cooling to rt, the solvent was removed under reduced pressure. The residue was diluted with EtOAc ( 1 L) and was washed with brine (200 mL x 3). The organic layer was dried over MgS04, filtered, and concentrated to afford ethyl 3-bromo-lH-pyrazole- 4-carboxylate (106 mmol, 23.2 g, 81 percent) and was used without any purification.LC-MS: m/z ES+= 219, 221.
Reference: [1] Patent: US2012/108619, 2012, A1, . Location in patent: Page/Page column 26
[2] Patent: WO2012/9009, 2012, A2, . Location in patent: Page/Page column 56
[3] Patent: WO2012/8999, 2012, A2, . Location in patent: Page/Page column 75
[4] Journal of Organic Chemistry, 2012, vol. 77, # 22, p. 10050 - 10057
[5] Patent: WO2014/188211, 2014, A1, . Location in patent: Page/Page column 78
[6] Patent: WO2018/64119, 2018, A1, . Location in patent: Paragraph 0499; 0505; 0935
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