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[ CAS No. 1408334-75-7 ] {[proInfo.proName]}

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Chemical Structure| 1408334-75-7
Chemical Structure| 1408334-75-7
Structure of 1408334-75-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1408334-75-7 ]

CAS No. :1408334-75-7 MDL No. :MFCD16619492
Formula : C5H7IN2O Boiling Point : -
Linear Structure Formula :- InChI Key :BQTYRYUORKTCJO-UHFFFAOYSA-N
M.W : 238.03 Pubchem ID :57886737
Synonyms :

Calculated chemistry of [ 1408334-75-7 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.17
TPSA : 38.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : 0.13
Log Po/w (WLOGP) : 0.48
Log Po/w (MLOGP) : 0.46
Log Po/w (SILICOS-IT) : 1.03
Consensus Log Po/w : 0.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.68
Solubility : 5.01 mg/ml ; 0.021 mol/l
Class : Very soluble
Log S (Ali) : -0.49
Solubility : 77.9 mg/ml ; 0.327 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.6
Solubility : 5.97 mg/ml ; 0.0251 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.12

Safety of [ 1408334-75-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1408334-75-7 ]

* 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 [ 1408334-75-7 ]
  • Downstream synthetic route of [ 1408334-75-7 ]

[ 1408334-75-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1408334-75-7 ]
  • [ 879488-19-4 ]
Reference: [1] Patent: WO2014/37750, 2014, A1,
  • 2
  • [ 3469-69-0 ]
  • [ 540-51-2 ]
  • [ 1408334-75-7 ]
YieldReaction ConditionsOperation in experiment
64%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1 h;
Stage #2: at 0 - 65℃; for 72 h;
Preparation 57: 2-(4-iodo-1 H-pyrazol-1 -yl)ethanol A solution of 4-iodo-1 H-pyrazole (4.50 g, 23.20 mmol) in DMF (45 mL) was treated with sodium hydride (60percent w/w, 1 .42 g, 35.5 mmol) at 0°C and stirred at room temperature. After 1 hour the resulting mixture was treated with 2-bromoethanol (2.5 mL, 35.2 mmol) at 0°C. The resulting mixture was heated to 65 °C for 3 days. The reaction quenched with brine/EtOAc and the aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried and concentrated. The residue was purified by silica gel column chromatography eluting with 0 to 50percent EtOAc in cyclohexane to give the title compound (3.55 g, 64percent). 1 H NMR (500 MHz, CDCI3): δ 7.55 (s, 1 H), 7.52 (s, 1 H), 4.32 - 4.22 (m, 2H), 4.04 - 3.95 (m, 2H), 2.79 - 2.68 (br m, 1 H). LCMS (ESI) Rt = 1 .50 minutes MS m/z 238 [M+H]+
Reference: [1] Patent: WO2014/37750, 2014, A1, . Location in patent: Paragraph 00142-00144
  • 3
  • [ 96-49-1 ]
  • [ 3469-69-0 ]
  • [ 1408334-75-7 ]
YieldReaction ConditionsOperation in experiment
53% at 125℃; for 24 h; a.
2-(4-Iodo-pyrazol-1-yl)-ethanol (Intermediate Aa)
A solution of 4-iodopyrazole (14.3 g, 73.9 mmol) and ethylene carbonate (6.83g, 77.6 mmol) in DMF (50 mL) was stirred at 125° C. for 24 h.
The cooled solution was concentrated under vacuum to leave a brown oil.
The residue was purified by FCC using 30-70percent EtOAc in DCM to give the title compound (9.36 g, 53percent). LCMS (Method 3): Rt 2.24 min, m/z 239 [MH+].
53% at 125℃; for 24 h; A solution of 4-iodopyrazole (14.3 g, 73.9 mmol) and ethylene carbonate (6.83g, 77.6 mmol) in DMF (50 mL) was stirred at 125 °C for 24 h. The cooled solution was concentrated under vacuum to leave a brown oil. The residue was purified by FCC, using 30-70percent EtOAc in DCM, to give the title compound (9.36 g, 53percent). LCMS (Method 3): Rt 2.24 min, m/z 239 [MH+].
53% at 125℃; for 24 h; A solution of 4-iodopyrazole (14.3 g, 73.9 mmol) and ethylene carbonate (6.83g, 77.6 mmol) in DMF (50 mL) was stirred at 125°C for 24 h. The cooled solution was concentrated under vacuum to leave a brown oil. The residue was purified by FCC using 30-70percent EtOAc in DCM to give the title compound (9.36 g, 53percent). LCMS (Method 3): Rt 2.24 min, m/z 239 [MH+].
53% at 125℃; for 24 h; A solution of 4-iodopyrazole (14.3 g, 73.9 mmol) and ethylenecarbonate (6.83g, 77.6 mmol) in DMF (50 mL) was stirred at 125 °C for 24 h.The cooled solution was concentrated under vacuum to leave a brown oil. Theresidue was purified by FCC, using 30-70percent EtOAc in DCM, to give the titlecompound (9.36 g, 53percent).

Reference: [1] Patent: US2014/364411, 2014, A1, . Location in patent: Paragraph 0423; 0424
[2] Patent: WO2014/194956, 2014, A1, . Location in patent: Page/Page column 42
[3] Patent: WO2014/195400, 2014, A1, . Location in patent: Page/Page column 92
[4] Patent: KR2016/16973, 2016, A, . Location in patent: Paragraph 0221-0223
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