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Chemical Structure| 331765-71-0
Chemical Structure| 331765-71-0
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Product Details of [ 331765-71-0 ]

CAS No. :331765-71-0 MDL No. :MFCD04035649
Formula : C7H3F2NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZBEWIPTYUHHZIS-UHFFFAOYSA-N
M.W : 203.10 Pubchem ID :2783365
Synonyms :

Calculated chemistry of [ 331765-71-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.14
TPSA : 83.12 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) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.63
Log Po/w (XLOGP3) : 1.48
Log Po/w (WLOGP) : 2.41
Log Po/w (MLOGP) : 1.38
Log Po/w (SILICOS-IT) : -0.02
Consensus Log Po/w : 1.18

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.22
Solubility : 1.23 mg/ml ; 0.00607 mol/l
Class : Soluble
Log S (Ali) : -2.83
Solubility : 0.299 mg/ml ; 0.00147 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.72
Solubility : 3.91 mg/ml ; 0.0192 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 331765-71-0 ]

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 [ 331765-71-0 ]

* 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 [ 331765-71-0 ]
  • Downstream synthetic route of [ 331765-71-0 ]

[ 331765-71-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 331765-71-0 ]
  • [ 126674-78-0 ]
YieldReaction ConditionsOperation in experiment
99% With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 4 h; Step 2: Compound 273 (80 g, 394 mmol) and palladium on carbon (9 g, 10percent wt) in EtOAc (900 ml) were stirred at room temperature under an atmosphere of H2 (50 bar) for 4 hours. The reaction mixture was filtered on a pad of silica and celite and the solvent removed in vacuo to give compound 274 as a pale yellow solid (67.39 g, 99percent yield, -95percent purity-NMR). This material was taken into the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.39 (ddd, J= 1 1.5, 8.4, 3.0Hz, 1 H), 7.3 (ddd, J=9.6, 3.0, 1 .8 Hz, 1 H)
54%
Stage #1: With ammonium acetate; ammonia; zinc In water for 1 h; Heating / reflux
Stage #2: at 0℃;
The product of Step 4 (435 mg), NH4OAc (100 mg) and conc. NH4OH (10 ml) were mixed together and Zn (1.0 g) was added in portions. (Caution: exotherm was detected after addition of Zn to the mixture.) After several minutes, the resulting mixture was heated at reflux for 1 h. The solution was cooled, filtered and concentrated to provide a beige solid. The solid was triturated with hot water, collected and dried by co-evaporation with toluene (3 x 10 ml) to give the desired product (200 mg) as a white solid in 54percent yield which was used directly in the next step
Reference: [1] Patent: WO2013/132376, 2013, A1, . Location in patent: Page/Page column 234-235
[2] Patent: EP1214299, 2004, B1, . Location in patent: Page 18
  • 2
  • [ 455-40-3 ]
  • [ 331765-71-0 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: at 20℃; for 1 h;
Stage #2: at 20 - 45℃;
Step 1 : 3,5-difluorobenzoic acid (80 g, 506 mmol) and sulfuric acid ( 250 ml) were stirred at room temperature for one hour. Then nitric acid (90 ml) was added, keeping the internal temperature below 45C with a water bath. The mixture was left at room temperature overnight. The reaction was poured slowly into ice and the resulting solid was filtered and washed with cold water to give compound 273 as a white solid (93.0 g, 91 percent yield). This material was taken into the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 8.01 (ddd, J=10.9, 8.5, 2.8 Hz, 1 H), 7.71 ( dt, J= 8.4, 2.2 Hz, 1 H).
34%
Stage #1: at 20℃; for 20 h;
Stage #2: at 0℃;
To 3,5-difluorobenzoic acid (1.0 g) was added HNO3 (90percent fuming; 3 ml). The homogeneous solution was stirred at RT for 20 h, then poured into ice water (150 ml). The solution was extracted with CH2Cl2, and the combined CH2Cl2 layers were dried over Na2SO4. Filtration and concentration gave the desired intermediate (435 mg) as a white solid in 34percent yield and was used directly in the next step.
Reference: [1] Patent: WO2013/132376, 2013, A1, . Location in patent: Page/Page column 234
[2] Patent: EP1214299, 2004, B1, . Location in patent: Page 18
[3] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 7, p. 2733 - 2743
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