Home Cart 0 Sign in  
X

[ CAS No. 42027-81-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 42027-81-6
Chemical Structure| 42027-81-6
Chemical Structure| 42027-81-6
Structure of 42027-81-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 42027-81-6 ]

Related Doc. of [ 42027-81-6 ]

Alternatived Products of [ 42027-81-6 ]

Product Details of [ 42027-81-6 ]

CAS No. :42027-81-6 MDL No. :MFCD06740528
Formula : C5H7N3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :WHPWNPMESFLXQT-UHFFFAOYSA-N
M.W : 157.13 Pubchem ID :162055
Synonyms :

Calculated chemistry of [ 42027-81-6 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.28
TPSA : 83.87 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) : -7.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.87
Log Po/w (XLOGP3) : -0.69
Log Po/w (WLOGP) : -0.22
Log Po/w (MLOGP) : -1.57
Log Po/w (SILICOS-IT) : -2.02
Consensus Log Po/w : -0.72

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 : 47.7 mg/ml ; 0.303 mol/l
Class : Very soluble
Log S (Ali) : -0.6
Solubility : 39.8 mg/ml ; 0.253 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.01
Solubility : 153.0 mg/ml ; 0.973 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.04

Safety of [ 42027-81-6 ]

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 [ 42027-81-6 ]

* 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 [ 42027-81-6 ]
  • Downstream synthetic route of [ 42027-81-6 ]

[ 42027-81-6 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 2075-46-9 ]
  • [ 540-51-2 ]
  • [ 42027-81-6 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In ethyl bromide; acetonitrile for 16 h; Reflux [0214j A mixture of 2-bromoethanol (3.75 g, 30.00 mmol), 4-nitropyrazzole (3.39 g, 30.00 mmol) and K2C03 (4.97 g, 36.00 mmol) in acetonitrile (30 mL) was refluxed for 16 h. Then the mixture was filtered and the filtrate was concentrated to dryness to give crude product 2-(4-nitro-1H-pyrazol-1-yl)ethanol as a white solid (4.70 g, yield: 100percent), which was used directly in the next step. ESI-MS (M+H) : 158.0.
94% With potassium carbonate In acetonitrile at 60℃; for 6 h; A solution of 2b (0.8g, 7.08mmol), 2-bromoethan-l-ol (0.97g, 7.76mmol) and K2CO3 (1.46g, 10.56mmol) in acetonitrile (15mL) was heated at 600C for 6h, then the solvent was evaporated and the residue was added water (15mL), extracted with ethyl acetate (10mLx3), dried with MgSO4 and concentrated to give 9a (1.05g, 94percent) as white solid.
61% With potassium carbonate In acetonitrile at 80℃; for 18 h; A solution of 4-nitropyrazole (300 rro, 0.27 mmol, I eq.), 2-bromoethanol (206 4,0.29 mmol, 1.1 eq.) and K2C03 (549 mg, 0.40 mmol, 1.5 eq.) in CH3CN (5mL) was heated to 80 °C for 18 h. The mixiure was allowed to cool and parlitioned between EtOAc (3 x 30 mL) and water (20 mL). The organic layers were dried over MgSO4, evaporated, and the residue purified by MPLC on SiC2 with gradient elution from 30-60percent EtOAc/petrolto give 2-(4-Nitro-IH-pyrazol-1- y[)ethanol as a white solid (256 mg, 61percent).
50% With potassium carbonate In acetonitrile at 95℃; Into a 250 mL round-bottom flask, was placed a solution of compound 28.1 (5 g, 44.22 mmol, 1.00 equiv) in CH3CN (100 mL), 2-bromoethan-1- ol (11 g, 88.02 mmol, 2.00 equiv) and potassium carbonate (18.5 g, 133.85 mmol, 3.00 equiv). The resulting solution was stirred overnight at 95°C in an oil bath. The reaction was then quenched by the addition of water and extracted with 3 x 100 mL of ethyl acetate. Organic layers were combined and concentrated under vacuum. The product crude was purified using flash column chromatography to furnish 3.5 g (50percent) of intermediate 28.2 as yellow oil.
49.5% With potassium carbonate In acetonitrile at 60℃; for 16 h; 2-Bromoethanol (1.9 g, 15.57 mmol) and potassium carbonate (2.9 g, 21.12 mmol) were added to a solution of 4-nitropyrazole (1.6 g, 14.16 mmol) in acetonitrile (20 mL) in sequence, the mixture was heated to 60° C. and stirred for 16 hours. After cooled to room temperature, the mixture was filtrated, the filtrate was concentrated under reduced pressure to give compound 51-b (1.1 g, yield: 49.5percent), which was used directly for the next step without purification.
43% With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 6 h; A stirred solution of 4-nitro-1H-pyrazole 12 (10.0 g, , 88.4 mmol), 2-bromo ethanol (12.0 g, 97.3 mmol) and cesium carbonate (43.0 g, 132.6 mmol) in DMF (130 mL) was heated to 100°C for 6h. After the completion of reaction (TLC monitoring), the reaction mixture was cooled to RT, diluted with water (200 mL) and extracted with EtOAc (2 x 200 mL). The combined organic phase washed with water, dried over Na2SO4, concentrated to give 2-(4-nitro-1H-pyrazol-1-yl)ethanol 17 (6.0 g, 43percent yield). ‘I-INMR (400 MHz, DMSO-d6): ö 8.81 (s, 1H), 8.26 (s, 1H), 4.99 (t, 1H), 4.22 (t, 2H) 3.76-3.78 (m, 2H).

Reference: [1] Patent: WO2015/89337, 2015, A1, . Location in patent: Paragraph 0214
[2] Patent: WO2009/154769, 2009, A1, . Location in patent: Page/Page column 41
[3] Patent: WO2016/42341, 2016, A1, . Location in patent: Page/Page column 183; 184
[4] Patent: WO2015/48281, 2015, A1, . Location in patent: Paragraph 00413; 00414
[5] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0342; 0343
[6] Patent: WO2015/25197, 2015, A1, . Location in patent: Paragraph 00080
[7] Patent: WO2007/99326, 2007, A1, . Location in patent: Page/Page column 112
[8] Patent: WO2012/110986, 2012, A1, . Location in patent: Page/Page column 43
[9] Patent: WO2013/17479, 2013, A1, . Location in patent: Page/Page column 48
[10] Patent: US2018/208604, 2018, A1, . Location in patent: Paragraph 0301-0302
  • 2
  • [ 1346672-86-3 ]
  • [ 42027-81-6 ]
Reference: [1] Patent: WO2013/164323, 2013, A1, . Location in patent: Page/Page column 55; 56
  • 3
  • [ 42027-81-6 ]
  • [ 948570-74-9 ]
Reference: [1] Patent: WO2015/48281, 2015, A1,
  • 4
  • [ 42027-81-6 ]
  • [ 948571-47-9 ]
YieldReaction ConditionsOperation in experiment
87% With palladium on activated charcoal; hydrogen In methanol at 20℃; for 1 h; Synthesis of compound 22.2. A 50-mL round-bottom flask, was charged with compound 21.1 (100 mg, 0.64 mmol, 1.00 equiv), methanol (5 mL) and palladium on carbon (20 mg). Resulting solution was stirred under H2 gas atmosphere for 1 h at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum to furnish 70 mg (87percent) of compound 22.2 as off-white oil.
83% With palladium 10% on activated carbon; hydrogen In ethanol at 25℃; for 12 h; Under hydrogen (1 atm), to a solution of compound 51-b (1.1 g, 7 mmol) in ethanol (20 mL) was added 10percent Pd—C (0.2 g). The mixture was stirred at 25° C. for 12 hours, and then filtrated, the filtrate was concentrated under reduced pressure to give compound 51-a (740 mg, yield: 83percent)), which was used directly for the next step without purification. LC-MS (ESI): m/z=128 [M+H]+.
81% With hydrogen; palladium(II) hydroxide In ethanol for 14 h; To a stirred solution of 2-(4-nitro-1H-pyrazol-1-yl)ethanol 17 (2.0 g, 1.23 mmol) in EtOH (25 mL), 0.40 g of Pd(OH)2 added and then stirred reaction under H2 gas atm for 1 4h. After the completion of reaction (TLC monitoring) the reaction mixture was filtered through celite bed, washed with MeOH, concentrated the solvent and the crude compound was purified by triturating with ether and pentane to give 2-(4-amino-1H- pyrazol-1-yl)ethanol precursor-07 as brown solid (1.30 g, 81percent yield). MS: 128.07 (M+H).
Reference: [1] Patent: WO2016/42341, 2016, A1, . Location in patent: Page/Page column 184
[2] Patent: WO2015/164374, 2015, A1, . Location in patent: Paragraph 00338; 00339
[3] Patent: US2015/336982, 2015, A1, . Location in patent: Paragraph 0342; 0344
[4] Patent: WO2015/25197, 2015, A1, . Location in patent: Paragraph 00081
[5] Patent: WO2007/99326, 2007, A1, . Location in patent: Page/Page column 113
[6] Patent: WO2012/110986, 2012, A1, . Location in patent: Page/Page column 56
[7] Patent: WO2013/17479, 2013, A1, . Location in patent: Page/Page column 48
[8] Patent: WO2015/48281, 2015, A1, . Location in patent: Paragraph 00413; 00415
[9] Patent: US2018/208604, 2018, A1, . Location in patent: Paragraph 0303-0304
  • 5
  • [ 42027-81-6 ]
  • [ 74-88-4 ]
  • [ 948570-75-0 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With sodium hydride In N,N-dimethyl-formamide for 0.5 h; Inert atmosphere
Stage #2: at 20℃; for 16 h; Inert atmosphere
Into a 100 mL round-bottom flask purged and maintained under inert atmosphere of nitrogen, were placed compound 33.1 (500 mg, 3.18 mmol, 1.00 equiv) in 10 mL of distilled DMF. This was followed by the addition of sodium hydride (191 mg, 7.96 mmol, 1.50 equiv) in portions. After stirring for 30 mm, Mel (2.26 g, 15.92 mmol, 5.00 equiv) was added dropwise via syringe and the resulting solution was stirred for 16 h at room temperature. The reaction was then quenched with 50 mL of water, extracted with 3 x 60 mL of ethyl acetate. The organic layers were combined and washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified using flash column chromatography to furnish 420 mg (77percent) of intermediate 33.2 as a yellow solid.
Reference: [1] Patent: WO2015/48281, 2015, A1, . Location in patent: Paragraph 00426; 00427
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 42027-81-6 ]

Alcohols

Chemical Structure| 1479085-67-0

[ 1479085-67-0 ]

(4-Nitro-1H-pyrazol-5-yl)methanol

Similarity: 0.78

Chemical Structure| 948571-47-9

[ 948571-47-9 ]

2-(4-Amino-1H-pyrazol-1-yl)ethanol

Similarity: 0.77

Chemical Structure| 6314-23-4

[ 6314-23-4 ]

2-(1-Pyrazolyl)ethanol

Similarity: 0.66

Chemical Structure| 98484-49-2

[ 98484-49-2 ]

3-(1H-Pyrazol-1-yl)propane-1,2-diol

Similarity: 0.62

Chemical Structure| 84547-61-5

[ 84547-61-5 ]

(1-Methyl-1H-pyrazol-5-yl)methanol

Similarity: 0.59

Nitroes

Chemical Structure| 948570-75-0

[ 948570-75-0 ]

1-(2-Methoxyethyl)-4-nitro-1H-pyrazole

Similarity: 0.95

Chemical Structure| 6645-69-8

[ 6645-69-8 ]

2-(4-Nitro-1H-pyrazol-1-yl)acetic acid

Similarity: 0.91

Chemical Structure| 3994-50-1

[ 3994-50-1 ]

1-Methyl-4-nitro-1H-pyrazole

Similarity: 0.85

Chemical Structure| 1479085-67-0

[ 1479085-67-0 ]

(4-Nitro-1H-pyrazol-5-yl)methanol

Similarity: 0.78

Chemical Structure| 92534-69-5

[ 92534-69-5 ]

1-Methyl-4-nitro-1H-pyrazole-5-carboxylic acid

Similarity: 0.77

Related Parent Nucleus of
[ 42027-81-6 ]

Pyrazoles

Chemical Structure| 948570-75-0

[ 948570-75-0 ]

1-(2-Methoxyethyl)-4-nitro-1H-pyrazole

Similarity: 0.95

Chemical Structure| 6645-69-8

[ 6645-69-8 ]

2-(4-Nitro-1H-pyrazol-1-yl)acetic acid

Similarity: 0.91

Chemical Structure| 3994-50-1

[ 3994-50-1 ]

1-Methyl-4-nitro-1H-pyrazole

Similarity: 0.85

Chemical Structure| 1479085-67-0

[ 1479085-67-0 ]

(4-Nitro-1H-pyrazol-5-yl)methanol

Similarity: 0.78

Chemical Structure| 948571-47-9

[ 948571-47-9 ]

2-(4-Amino-1H-pyrazol-1-yl)ethanol

Similarity: 0.77