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[ CAS No. 2033-29-6 ] {[proInfo.proName]}

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Chemical Structure| 2033-29-6
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Product Details of [ 2033-29-6 ]

CAS No. :2033-29-6 MDL No. :MFCD12963764
Formula : C7H4Cl2N2O Boiling Point : -
Linear Structure Formula :- InChI Key :HQBYAESCKCDTDJ-UHFFFAOYSA-N
M.W : 203.03 Pubchem ID :9899148
Synonyms :

Calculated chemistry of [ 2033-29-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 48.94
TPSA : 48.65 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.44
Log Po/w (XLOGP3) : 1.82
Log Po/w (WLOGP) : 2.16
Log Po/w (MLOGP) : 2.02
Log Po/w (SILICOS-IT) : 3.43
Consensus Log Po/w : 2.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.8
Solubility : 0.322 mg/ml ; 0.00158 mol/l
Class : Soluble
Log S (Ali) : -2.46
Solubility : 0.702 mg/ml ; 0.00346 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.06
Solubility : 0.0178 mg/ml ; 0.0000879 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 2033-29-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2033-29-6 ]

* 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 [ 2033-29-6 ]
  • Downstream synthetic route of [ 2033-29-6 ]

[ 2033-29-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 2033-29-6 ]
  • [ 16865-11-5 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: for 3 h; Reflux
Stage #2: With sodium hydroxide In water at 20℃;
Thoroughly dried 5,6-dichloro- 1 ,3-dihydro-benzoimidazol-2-one (28.4 g, 0.14 mol) was suspended in POCI3 (75 ml_). The reaction solution was heated to reflux temperature for 3 hours and cooled to room temperature. The solution was poured into crushed ice/water (1.5 L) slowly with sufficient stirring. The solution was neutralized to pH = 7.0 with NaOH. The precipitated solid was collected by filtration, washed with water, and dried to afford the title compound (27.9 g, 90percent). The crude product was used in the following reaction without further purification.
71% at 120℃; for 2 h; a screw-cap pressure tube (b) Preparation of the intermediary compound 2,5,6-trichloro-l -benzo[d]imidazole:To 5,6-dichloro-lH-benzo[d]imidazol-2(3H)-one (1.0 g, 4.5 mmol) was added phosphoryl trichloride (4 mL) and the reaction mixture was heated in a screw-cap pressure tube at 12O0C for 2 hours. The reaction mixture was concentrated in vacuo, the residue was diluted with water (30 mL) and the resulting off-white solid was filtered off. The precipitate was washed with water (3x20 mL) and dried under high vacuum to afford 0.77 g (71 percent yield) of 2,5,6-trichloro-lH- benzo[d]imidazole.
71% at 120℃; for 2 h; To 5,6-dichloro-lH-benzo[d]imidazol-2(3H)-one (1.0 g, 4.5 mmol) was added phosphoryl trichloride (4 mL) and the reaction mixture was heated in a screw-cap pressure tube at 120°C for 2 hours. The reaction mixture was concentrated in vacuo, the residue was diluted with water (30 mL) and the resulting off-white solid was filtered off. The precipitate was washed with water (3 x20 mL) and dried under high vacuum to afford 0.77 g (71 percent yield) of 2,5,6-trichloro-lH- benzo[d]imidazole.
Reference: [1] Patent: WO2009/134750, 2009, A1, . Location in patent: Page/Page column 60
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 15, p. 7188 - 7211
[3] Patent: WO2011/23812, 2011, A1, . Location in patent: Page/Page column 69
[4] Patent: WO2012/117062, 2012, A1, . Location in patent: Page/Page column 29
[5] Journal of Medicinal Chemistry, 1997, vol. 40, # 4, p. 586 - 593
[6] Patent: EP1698635, 2006, A1, . Location in patent: Page/Page column 28
[7] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 5010 - 5014
[8] European Journal of Medicinal Chemistry, 2009, vol. 44, # 3, p. 1024 - 1033
[9] Patent: WO2013/63221, 2013, A1, . Location in patent: Page/Page column 29
[10] Patent: WO2008/129007, 2008, A1, . Location in patent: Page/Page column 35-36
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