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[ CAS No. 112029-98-8 ] {[proInfo.proName]}

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Chemical Structure| 112029-98-8
Chemical Structure| 112029-98-8
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Product Details of [ 112029-98-8 ]

CAS No. :112029-98-8 MDL No. :MFCD01822311
Formula : C5H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :QSXREDPBMQKKAY-UHFFFAOYSA-N
M.W : 112.13 Pubchem ID :11961423
Synonyms :

Calculated chemistry of [ 112029-98-8 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 29.62
TPSA : 38.05 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) : -7.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.17
Log Po/w (XLOGP3) : -0.65
Log Po/w (WLOGP) : -0.24
Log Po/w (MLOGP) : -0.53
Log Po/w (SILICOS-IT) : 0.19
Consensus Log Po/w : -0.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.52
Solubility : 33.7 mg/ml ; 0.3 mol/l
Class : Very soluble
Log S (Ali) : 0.32
Solubility : 237.0 mg/ml ; 2.11 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.57
Solubility : 30.4 mg/ml ; 0.271 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.12

Safety of [ 112029-98-8 ]

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

Application In Synthesis of [ 112029-98-8 ]

* 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 [ 112029-98-8 ]
  • Downstream synthetic route of [ 112029-98-8 ]

[ 112029-98-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 25016-11-9 ]
  • [ 112029-98-8 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: With sodium tetrahydroborate In methanol at 20℃; for 3 h;
Stage #2: With hydrogenchloride; methanol In water at 0 - 20℃;
The compound of formula IX (3.48 g, 31.6 mmol) was dissolved in methanol (25 ml_) and sodium borohydride (2.50 g, 66.1 mmol, 2.09 equiv.) was added portion-wise with vigorous gas evolution. After stirring for 3 hours at room temperature, the reaction was cooled to 0 0C and slowly acidified to pH ~ 1 with 4N aqueous hydrochloric acid (20 ml_) over 55 minutes. A thick white slurry formed and this was stirred one hour at room temperature. The reaction was then basified by the gradual addition of saturated aqueous potassium carbonate solution (53.4 wtpercent K2CU3, 6.04 M; 10 ml_). This resulted in a clear, colorless solution (pH = 1.1), which was diluted with additional saturated potassium carbonate solution (200 ml_) and was extracted with ethyl acetate (2 x 200 ml_). The ethyl acetate extracts were combined, dried over sodium sulfate, filtered and concentrated to yield the compound of formula X as a light yellow oil (3.44 g, 97percent yield).
60.5% at 0 - 20℃; for 1 h; Step A
(1-methyl-1,1-pyrazol-4-yl)methanol
To a solution of 1-methyl-1H-pyrazole-4-carbaldehyde (0.500 g, 4.54 mmol) in methanol (10 mL, 200 mmol) at 0° C. was added sodium tetrahydroboride (0.515 g, 13.6 mmol).
The reaction was stirred at room temperature for 1 h, and then quenched with brine, and extracted with ethyl acetate (EtOAc) (3*).
The combined organic phases were washed with water, brine, dried over Na2SO4, and concentrated to give 0.308 g (60.5percent yield) of the final product as colorless oil, which was used directly for the next step without further purification. LC/MS found: 113.1 (M+1)+.
400 mg With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2 h; Cooling with ice Intermediate 69 (600mg, 1 eq.) was dissolved in tetrahydrofuran, and lithium aluminum hydride (210 mg, 1 eq.) was added under ice bath and the mixture was reacted at room temperature for 2 h. After completion of the reaction, 210 µl of water, 210 µl of 10percent aqueous sodium hydroxide solution, and 630 µl of water were successively added, followed by addition of anhydrous magnesium sulfate. The mixture was stirred for a while, filtered and evaporated to dryness to give 400 mg of an oil. MS (ESI): 113(M+H)
Reference: [1] Patent: WO2008/153870, 2008, A1, . Location in patent: Page/Page column 30
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 13, p. 3777 - 3787
[3] Russian Journal of General Chemistry, 2010, vol. 80, # 5, p. 1001 - 1003
[4] Patent: US2013/96144, 2013, A1, . Location in patent: Paragraph 0174
[5] Patent: EP3239135, 2017, A1, . Location in patent: Paragraph 0132; 0133
  • 2
  • [ 85290-80-8 ]
  • [ 112029-98-8 ]
YieldReaction ConditionsOperation in experiment
93% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 60℃; A solution of ethyl 1 -methyl- lH-pyrazole-4-carboxylate (1.16 g, 7.52 mmol) in THF (13.3 mL) was added into a solution of lithium aluminiumhydride (1.0 M in THF, 15.05 mL, 15.05 mmol) in THF (53 mL) dropwise at 0 °C. The resulting mixture was allowed to heat at 60 °C for lh. After lh, the reaction was allowed to cool to rt. Sodium sulfate decahydrate (4.0 g) was added portion wise and the resulting mixture was stirred for lh at rt. EtOAc (150mL) was added and the resulting mixture was stirred overnight. The mixture was filtered through a pad of celite and the residual solid was washed with EtOAc several times. The filtrate was concentrated in vacuo to afford the title compound as colorless oil (790 mg, 93percent).1H NMR (400 MHz, CDC13) δ 7.49 (s, 1H), 7.39 (s, 1H), 4.59 (s, 2H), 3.90 (s, 3H).
62% With lithium aluminium tetrahydride In tetrahydrofuran at 25 - 30℃; for 3 h; Inert atmosphere; Cooling Lithium aluminium hydride (320 mL, 0.32 mole, 1M in THF) was added to acooled solution of ethyl 1-methyl-1H-pyrazole-4-carboxylate (32.34 g, 0.21 mole) inTHF (300 mL) under stirring in N2 atmosphere. The reaction mixture was warmed toRT and stirred further for 3 hours. The reaction mixture was cooled to 0 °C, dilutedwith ethyl acetate and treated with water (25 mL). The mixture was filtered throughcelite bed and concentrated under vacuum to obtain the crude compound which was further purified by flash chromatography (ethyl acetate: methanol (98:2)) to afford (1- methyl- 1H-pyrazol-4-yl)-methanol.Yield: 14.66 g (62 percent); ‘H - NMR (CDC13, 400 MHz) ö ppm: 1.98 (bs, 1H), 3.88 (s,3H), 4.56 (s, 2H), 7.36 (s, 1H), 7.45 (s, 1H); Mass (mlz): 113.1 (M+H).
Reference: [1] Patent: WO2018/89786, 2018, A1, . Location in patent: Paragraph 00395
[2] Patent: WO2017/42643, 2017, A1, . Location in patent: Page/Page column 23
  • 3
  • [ 100852-80-0 ]
  • [ 112029-98-8 ]
Reference: [1] Patent: US2008/125467, 2008, A1, . Location in patent: Page/Page column 20
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