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[ CAS No. 1018446-95-1 ] {[proInfo.proName]}

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Chemical Structure| 1018446-95-1
Chemical Structure| 1018446-95-1
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Product Details of [ 1018446-95-1 ]

CAS No. :1018446-95-1 MDL No. :MFCD20697038
Formula : C8H13N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FIBAJOZIOKKYHC-UHFFFAOYSA-N
M.W : 183.21 Pubchem ID :59587648
Synonyms :

Calculated chemistry of [ 1018446-95-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.5
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.83
TPSA : 70.14 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) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 0.82
Log Po/w (WLOGP) : 1.26
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : -0.33
Consensus Log Po/w : 0.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.58
Solubility : 4.83 mg/ml ; 0.0264 mol/l
Class : Very soluble
Log S (Ali) : -1.88
Solubility : 2.44 mg/ml ; 0.0133 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.95
Solubility : 20.5 mg/ml ; 0.112 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.52

Safety of [ 1018446-95-1 ]

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 [ 1018446-95-1 ]

* 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 [ 1018446-95-1 ]
  • Downstream synthetic route of [ 1018446-95-1 ]

[ 1018446-95-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1018446-96-2 ]
  • [ 1018446-95-1 ]
YieldReaction ConditionsOperation in experiment
97% With palladium 10% on activated carbon; hydrogen In ethanol; water at 20℃; for 20 h; c) tert-Butyl 4-amino- 1H-pyrazole- 1 -carboxylate (A55) A suspension of ferf-butyl 4-nitro-1 --pyrazole-1 -carboxylate A54 (3.70 g, 17.4 mmol) and 10percent Pd/C wetted with ca. 53percent water (0.300 g) in EtOH (150 mL) were stirred under hydrogen (1 atm) at room temperature for 20 hours. The reaction mixture was then filtered through celite, the plug was washed with EtOAc (ca. 100 mL) and the filtrate concentrated under reduced pressure to give the title compound (3.09 g, 97percent) as a pale brown solid. H NMR (400 MHz, CDCI3) δ 7.54 (d, J = 0.6 Hz, 1 H), 7.40 (d, J = 0.8 Hz, 1 H), 3.10 (s, 2H), 1.62 (s, 9H). LCMS-A rt 3.75 min; no product ions detected.
95% With hydrogen In methanol at 60℃; A solution of terf-butyl 4-nitro-1 H-pyrazole-1-carboxylate (1.Og, 4.7mmol) in MeOH (120ml) was passed through the H-Cube with full hydrogen mode at 6O0C and 1 bar with a 10percent Pd/C cartridge using 1ml/min flow rate. The solution was then passed through the H-Cube for a second time using identical conditions and the solvent removed in vacuo to afford tert-butyl 4-amino-1 H-pyrazole-1-carboxylate (0.82g, 4.5mmol, 95percent). 1H NMR (DMSO) δ 1.54 (9H, s), 4.42 (2H, s), 7.33 (1H1 s), 7.35 (1H, s). LCMS (2) Rt: 1.45min; m/z (ES+) 206 M+Na+.
89% at 20℃; for 16 h; [0211j A mixture of tert-butyl 4-nitro-1H-pyrazole-1-carboxylate (3.00 g, 14.08 mmol)and palladium on charcoal (300 mg, 10percentwt) in ethanol (30 mL) was stirred at rt under H2atmosphere (balloon pressure) for 16 h. The catalyst was filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc = 1/1 with 0.0 1percent TEA) to give product tert-butyl 4-amino-1H-pyrazole-1- carboxylate as a white solid (2.30 g, yield: 89percent). ESI-MS (M+H) : 129.0. ‘H NMR (400 MHz, CDC13) (5: 7.59 (s, 1H), 7.43 (s, 1H), 1.63 (s, 9H).
72% With palladium 10% on activated carbon; hydrogen In methanol A round bottom flask was charged with tert-butyl 4-nitro-1H-pyrazole-1- carboxylate 57 (9.2g, 43.17 mmol) and methanol (400 mL) followed by addition of Pd-C (10percent w/w, 3.0 g). The flask was evacuated under vacuum and then purged with hydrogen. The reaction was stirred under hydrogen atmosphere (30 psi). The reaction was monitored by TLC. It was then filtered through sintered funnel with a pad of celite, washed with methanol and concentrated under reduced pressure to afford precursor-3 1 as a brown solid (5.7 g, 72percent yield) that was taken as such for the next step without any further purification. 1H NMR (400 MHz, DMSO-d6): 8 7.32-7.34 (m, 1H), 6.98 (s, 1H), 4.40 (s, 2H), 1.53 (s, 9H).
70% With hydrogen In methanol at 20℃; for 48 h; (1a)
tert-butyl 4-amino-1H-pyrazole-1-carboxylate
4-Nitro-1H-pyrazole (20 g), triethylamine (27 mL) and di-tert-butyl dicarbonate (42.4 g) were dissolved in acetonitrile (200 mL) solution, and the mixture was stirred at room temperature for 3 days.
The solvent was evaporated under reduced pressure, and the residue was washed with water and hexane to give tert-butyl 4-nitro-1H-pyrazole-1-carboxylate as a yellow solid (32.76 g).
The compound was dissolved in methanol (250 mL), palladium carbon (6.6 g) was added, and the mixture was stirred at room temperature for 2 days under a hydrogen atmosphere.
The catalyst was filtered through celite, and the filtrate was concentrated to give tert-butyl 4-amino-1H-pyrazole-1-carboxylate (19.5 g, 70percent).
1H NMR (300 MHz, DMSO-d6) δ ppm 1.53 (s, 9H) 4.39 (s, 2H) 7.34 (d, J=4.92 Hz, 2H)
62% With hydrogen In methanol at 60℃; for 15 h; To a 500 niL flask were added ieri-butyl-4-nitro-lH-pyrazole-l-carboxylate (1.15 g, 5.00 mmol), 10percent Pd/C (300 mg) followed by addition of MeOH (150 niL). The resulting mixture was stirred at 60 °C under H2 balloon for 15 hours. The mixture was filtered with Celite and the filtrate was concentrated by vacuum. The residue was purified by column chromatography on silica gel with EtOAc/petroleum ether (1/6) to afford the desired product as a yellow solid (0.6 g, 62percent yield). 3/4 NMR (DMSO- , 500 MHz): δ 7.34 (s, 1H), 7.32 (s, 1H), 4.40 (s, 2H), 1.53 (s, 9H).
680 mg With palladium on activated charcoal; hydrogen In ethanol Tert-butyl 4-nitro-1H-pyrazole-1-carboxylate was dissolved in 40 mL of EtOH, then 200 mg of Pd/C was added and the mixture was stirred under H2 at ambient pressure overnight. The catalyst was filtered off and the solvent was evaporated to afford tert-butyl 4-amino-1H-pyrazole-1-carboxylate (680 mg, 92percent yield) as a pale pink solid. MS found for C8H13N3O2 as (M+H)+ 184.0.

Reference: [1] Patent: WO2014/128465, 2014, A1, . Location in patent: Page/Page column 79
[2] Patent: WO2008/139161, 2008, A1, . Location in patent: Page/Page column 197
[3] Patent: WO2015/89337, 2015, A1, . Location in patent: Paragraph 0211
[4] Patent: WO2015/25197, 2015, A1, . Location in patent: Paragraph 000128
[5] Patent: US2009/325956, 2009, A1, . Location in patent: Page/Page column 38
[6] Patent: WO2011/113802, 2011, A2, . Location in patent: Page/Page column 110
[7] Advanced Synthesis and Catalysis, 2014, vol. 356, # 8, p. 1719 - 1724
[8] Patent: WO2016/196776, 2016, A2, . Location in patent: Paragraph 001217
  • 2
  • [ 24424-99-5 ]
  • [ 1018446-95-1 ]
Reference: [1] Patent: WO2011/113802, 2011, A2,
[2] Patent: WO2014/128465, 2014, A1,
[3] Patent: WO2015/25197, 2015, A1,
[4] Patent: WO2015/89337, 2015, A1,
[5] Patent: WO2016/196776, 2016, A2,
[6] Patent: WO2008/139161, 2008, A1,
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