Alternatived Products of [ 5175-26-8 ]
Product Details of [ 5175-26-8 ]
CAS No. : 5175-26-8
MDL No. : MFCD06797225
Formula :
C6 H4 N2 O3
Boiling Point : -
Linear Structure Formula : -
InChI Key : XOVNMCWPVHPBED-UHFFFAOYSA-N
M.W : 152.11 Pubchem ID : 53424747
Synonyms :
Calculated chemistry of [ 5175-26-8 ]
Physicochemical Properties
Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.45
TPSA : 75.78 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) : 0.47
Log Po/w (XLOGP3) : 0.48
Log Po/w (WLOGP) : 0.8
Log Po/w (MLOGP) : -0.51
Log Po/w (SILICOS-IT) : -0.64
Consensus Log Po/w : 0.12
Druglikeness
Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55
Water Solubility
Log S (ESOL) : -1.36
Solubility : 6.68 mg/ml ; 0.0439 mol/l
Class : Very soluble
Log S (Ali) : -1.64
Solubility : 3.48 mg/ml ; 0.0229 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.34
Solubility : 6.98 mg/ml ; 0.0459 mol/l
Class : Soluble
Medicinal Chemistry
PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79
Application In Synthesis of [ 5175-26-8 ]
* 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 [ 5175-26-8 ] Downstream synthetic route of [ 5175-26-8 ]
1
[ 5175-26-8 ]
[ 14205-39-1 ]
[ 177857-61-3 ]
cis-6-Methyl-2,4-bis-(2-nitro-3-pyridyl)-1,2,3,4-tetrahydropyrimidin-5-carbonsaeuremethylester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 11%
2: 12%
In ethanol; acetic acid for 24h; Ambient temperature;
2
[ 5175-26-8 ]
[ 105-45-3 ]
[ 177857-53-3 ]
Yield Reaction Conditions Operation in experiment
36%
With ammonium hydroxide In ethanol for 2h; Heating;
3
[ 5175-26-8 ]
[ 105-45-3 ]
cis-6-Methyl-2,4-bis-(2-nitro-3-pyridyl)-1,2,3,4-tetrahydropyrimidin-5-carbonsaeuremethylester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
29%
With ammonium hydroxide In ethanol for 24h; Ambient temperature;
Yield Reaction Conditions Operation in experiment
3-Dibrommethyl-2-nitro-pyridin, AgNO3, in sd. wss. A.;
5
[ 5175-26-8 ]
6,8-Dimethyl-9-oxo-9,10-dihydro-1,5,10-triazaphenanthren-7-carbonsaeuremethylester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 12 percent / ethanol; acetic acid / 24 h / Ambient temperature
2: 33 percent / methanol / 3 h / Irradiation
3: 45 percent / PCl3 / CH2 Cl2 / Heating
Multi-step reaction with 3 steps
1: 12 percent / ethanol; acetic acid / 24 h / Ambient temperature
2: 41 percent / methanol / 3 h / Irradiation
3: 62 percent / conc. HCl, SnCl2 / Heating
Multi-step reaction with 4 steps
1: 12 percent / ethanol; acetic acid / 24 h / Ambient temperature
2: 41 percent / methanol / 3 h / Irradiation
3: 58 percent / Zn, NH4 Cl / ethanol; H2 O
4: 45 percent / PCl3 / CH2 Cl2 / Heating
Multi-step reaction with 3 steps
1: 12 percent / ethanol; acetic acid / 24 h / Ambient temperature
2: 72 percent / aq. (NH4 )2Ce(NO3 )6 / acetone
3: 62 percent / conc. HCl, SnCl2 / Heating
Multi-step reaction with 4 steps
1: 12 percent / ethanol; acetic acid / 24 h / Ambient temperature
2: 72 percent / aq. (NH4 )2Ce(NO3 )6 / acetone
3: 58 percent / Zn, NH4 Cl / ethanol; H2 O
4: 45 percent / PCl3 / CH2 Cl2 / Heating
Reference：
[1]Goerlitzer; Ewert
[Pharmazie, 1996, vol. 51, # 4, p. 207 - 212]
[2]Goerlitzer; Ewert
[Pharmazie, 1996, vol. 51, # 4, p. 207 - 212]
[3]Goerlitzer; Ewert
[Pharmazie, 1996, vol. 51, # 4, p. 207 - 212]
[4]Goerlitzer; Ewert
[Pharmazie, 1996, vol. 51, # 4, p. 207 - 212]
[5]Goerlitzer; Ewert
[Pharmazie, 1996, vol. 51, # 4, p. 207 - 212]
6
[ 5175-26-8 ]
6,8-Dimethyl-9-oxo-9,10-dihydro-1,7,10-triazaphenanthren-5-carbonsaeuremethylester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 36 percent / 25percent NH3 / ethanol / 2 h / Heating
2: 80 percent / aq. (NH4 )2Ce(NO3 )6 / acetone / 0.17 h
3: 67 percent / conc. HCl, SnCl2 / 0.5 h / Heating
Multi-step reaction with 4 steps
1: 36 percent / 25percent NH3 / ethanol / 2 h / Heating
2: 80 percent / aq. (NH4 )2Ce(NO3 )6 / acetone / 0.17 h
3: 35 percent / Zn, NH4 Cl / ethanol; H2 O / 60 °C
4: 38 percent / PCl3 / CHCl3 / 0.5 h / Heating
7
[ 5175-26-8 ]
[ 177857-55-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 36 percent / 25percent NH3 / ethanol / 2 h / Heating
2: 80 percent / aq. (NH4 )2Ce(NO3 )6 / acetone / 0.17 h
3: 35 percent / Zn, NH4 Cl / ethanol; H2 O / 60 °C
8
[ 5175-26-8 ]
[ 177857-63-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 12 percent / ethanol; acetic acid / 24 h / Ambient temperature
2: 33 percent / methanol / 3 h / Irradiation
Multi-step reaction with 3 steps
1: 12 percent / ethanol; acetic acid / 24 h / Ambient temperature
2: 41 percent / methanol / 3 h / Irradiation
3: 58 percent / Zn, NH4 Cl / ethanol; H2 O
Multi-step reaction with 3 steps
1: 12 percent / ethanol; acetic acid / 24 h / Ambient temperature
2: 72 percent / aq. (NH4 )2Ce(NO3 )6 / acetone
3: 58 percent / Zn, NH4 Cl / ethanol; H2 O
Reference：
[1]Goerlitzer; Ewert
[Pharmazie, 1996, vol. 51, # 4, p. 207 - 212]
[2]Goerlitzer; Ewert
[Pharmazie, 1996, vol. 51, # 4, p. 207 - 212]
[3]Goerlitzer; Ewert
[Pharmazie, 1996, vol. 51, # 4, p. 207 - 212]
9
[ 5175-26-8 ]
3-Chlor-6,8-dimethyl-9-oxo-9,10-dihydro-1,7,10-triazaphenanthren-5-carbonsaeuremethylester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: 36 percent / 25percent NH3 / ethanol / 2 h / Heating
2: 63 percent / methanol / Irradiation
3: 63 percent / conc. HCl / 1 h / Ambient temperature
4: 53 percent / PCl3 / CH2 Cl2 / Heating
10
[ 5175-26-8 ]
[ 1026753-83-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 36 percent / 25percent NH3 / ethanol / 2 h / Heating
2: 63 percent / methanol / Irradiation
11
[ 5175-26-8 ]
[ 177857-59-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 36 percent / 25percent NH3 / ethanol / 2 h / Heating
2: 63 percent / methanol / Irradiation
3: 63 percent / conc. HCl / 1 h / Ambient temperature
12
[ 5175-26-8 ]
[ 177857-54-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 36 percent / 25percent NH3 / ethanol / 2 h / Heating
2: 80 percent / aq. (NH4 )2Ce(NO3 )6 / acetone / 0.17 h
13
[ 5175-26-8 ]
[ 177857-62-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 12 percent / ethanol; acetic acid / 24 h / Ambient temperature
2: 41 percent / methanol / 3 h / Irradiation
Multi-step reaction with 2 steps
1: 12 percent / ethanol; acetic acid / 24 h / Ambient temperature
2: 72 percent / aq. (NH4 )2Ce(NO3 )6 / acetone
14
[ 5175-26-8 ]
6-Methyl-2,4-bis-(2-nitro-3-pyridyl)-pyrimidin-5-carbonsaeuremethylester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 11 percent / ethanol; acetic acid / 24 h / Ambient temperature
2: 77 percent / aq. (NH4 )2Ce(NO3 )6 / acetone
Multi-step reaction with 2 steps
1: 29 percent / 25percent NH3 / ethanol / 24 h / Ambient temperature
2: 77 percent / aq. (NH4 )2Ce(NO3 )6 / acetone
15
[ 5175-26-8 ]
[ 7521-41-7 ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride
With hydrogenchloride; iron In ethanol; water at 70℃; for 1h; chemoselective reaction;
2.2 Representative procedure for the synthesis of 2-aminoaldehyde (6-Aminopiperonal as example)
General procedure: Step 1 3 mL of concentrated HNO3 was added to piperonal (7) (6.66 mmol; 1g) and mixed in a round-bottom flask under ice bath. The mixture was allowed to vigorous magnetic agitate in r.t. It is observed immediate change of color (colorless to yellow). TLC reveals the end of reaction in 2h. The isolation is performed through ice-bath cooling of reactional medium, observing immediate precipitation, which was vacuum filtered, washed with around 200mL of cold distilled water and recrystallized in ethanol/water. Light yellow solid, 1.171g, 90%. Step 2 The synthesis of 6-aminopiperonalAdd 6-nitropiperonal (780 mg) to a 30 ml solution of EtOH/water (3:1) with eletrolytic iron powder (1600 mg) and concentrated HCl (1 drop). The mixture was heated at 70 °C for 1 h until the completion was detected by TLC. The reaction mixture was allowed to cool to ambient temperature. Then the reaction mass was diluted with ethyl acetate and filtered through a plug of celite. The filtrate was concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel with ethyl acetate/petroleum ether (2:5) as eluent to afford 6-aminopiperonal(430 mg65%).
Reference：
[1]Location in patent: scheme or table
Wang, Kan; Herdtweck, Eberhardt; Doemling, Alexander
[ACS Combinatorial Science, 2012, vol. 14, # 5, p. 316 - 322]
[2]Yuan, Pengtao; Gu, Xiangyu; Ni, Xintong; Qi, Yingxue; Shao, Xusheng; Xu, Xiaoyong; Liu, Jianwen; Qian, Xuhong
[Bioorganic and Medicinal Chemistry Letters, 2021, vol. 51]
16
[ 5175-26-8 ]
[ 1373889-63-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: hydrogenchloride
2: sodium hydroxide / ethanol / 70 °C
Multi-step reaction with 2 steps
1: hydrogenchloride; iron / ethanol; water / 1 h / 70 °C
2: sodium hydroxide / ethanol / 0.5 h / 70 °C
Reference：
[1]Wang, Kan; Herdtweck, Eberhardt; Doemling, Alexander
[ACS Combinatorial Science, 2012, vol. 14, # 5, p. 316 - 322]
[2]Yuan, Pengtao; Gu, Xiangyu; Ni, Xintong; Qi, Yingxue; Shao, Xusheng; Xu, Xiaoyong; Liu, Jianwen; Qian, Xuhong
[Bioorganic and Medicinal Chemistry Letters, 2021, vol. 51]
17
[ 5175-26-8 ]
[ 1373889-37-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: hydrogenchloride
2: sodium hydroxide / ethanol / 70 °C
18
[ 5175-26-8 ]
[ 1373889-64-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: hydrogenchloride
2: N-methylcyclohexylamine / ethanol / Alkaline conditions
19
[ 5175-26-8 ]
[ 1373889-65-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: hydrogenchloride
2: sodium hydroxide / ethanol / 70 °C
20
[ 5175-26-8 ]
[ 1373889-66-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: hydrogenchloride
2: sodium hydroxide / ethanol / 70 °C
21
[ 5175-26-8 ]
[ 1373889-22-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: hydrogenchloride
2: sodium hydroxide / ethanol / 70 °C
22
[ 5175-26-8 ]
[ 1373889-23-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: hydrogenchloride
2: sodium hydroxide / ethanol / 70 °C
23
[ 5175-26-8 ]
[ 1373889-87-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: hydrogenchloride
2: sodium hydroxide / ethanol / 70 °C
3: 110 °C / neat (no solvent)
24
[ 5175-26-8 ]
C16 H12 N4 OS
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: hydrogenchloride
2: sodium hydroxide / ethanol / 70 °C
3: 110 °C / neat (no solvent)
25
[ 5175-26-8 ]
2-amino-N-(pyridin-3-ylmethyl)-1,8-naphthyridine-3-carboxamide
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: hydrogenchloride; iron / ethanol; water / 1 h / 70 °C
2: sodium hydroxide / ethanol / 0.5 h / 70 °C
Reference：
[1]Yuan, Pengtao; Gu, Xiangyu; Ni, Xintong; Qi, Yingxue; Shao, Xusheng; Xu, Xiaoyong; Liu, Jianwen; Qian, Xuhong
[Bioorganic and Medicinal Chemistry Letters, 2021, vol. 51]
26
[ 500-22-1 ]
[ 5175-26-8 ]
Yield Reaction Conditions Operation in experiment
With nitric acid at 0 - 20℃; for 2h; regioselective reaction;
2.2 Representative procedure for the synthesis of 2-aminoaldehyde (6-Aminopiperonal as example)
General procedure: Step 1 3 mL of concentrated HNO3 was added to piperonal (7) (6.66 mmol; 1g) and mixed in a round-bottom flask under ice bath. The mixture was allowed to vigorous magnetic agitate in r.t. It is observed immediate change of color (colorless to yellow). TLC reveals the end of reaction in 2h. The isolation is performed through ice-bath cooling of reactional medium, observing immediate precipitation, which was vacuum filtered, washed with around 200mL of cold distilled water and recrystallized in ethanol/water. Light yellow solid, 1.171g, 90%. Step 2 The synthesis of 6-aminopiperonalAdd 6-nitropiperonal (780 mg) to a 30 ml solution of EtOH/water (3:1) with eletrolytic iron powder (1600 mg) and concentrated HCl (1 drop). The mixture was heated at 70 °C for 1 h until the completion was detected by TLC. The reaction mixture was allowed to cool to ambient temperature. Then the reaction mass was diluted with ethyl acetate and filtered through a plug of celite. The filtrate was concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel with ethyl acetate/petroleum ether (2:5) as eluent to afford 6-aminopiperonal(430 mg65%).
Reference：
[1]Yuan, Pengtao; Gu, Xiangyu; Ni, Xintong; Qi, Yingxue; Shao, Xusheng; Xu, Xiaoyong; Liu, Jianwen; Qian, Xuhong
[Bioorganic and Medicinal Chemistry Letters, 2021, vol. 51]
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