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[ CAS No. 864076-05-1 ] {[proInfo.proName]}

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Chemical Structure| 864076-05-1
Chemical Structure| 864076-05-1
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Product Details of [ 864076-05-1 ]

CAS No. :864076-05-1 MDL No. :MFCD13189816
Formula : C6H7BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :ROEZBNMDDJUDSC-UHFFFAOYSA-N
M.W : 219.04 Pubchem ID :53302209
Synonyms :

Calculated chemistry of [ 864076-05-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.33
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.47
TPSA : 44.12 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) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 1.22
Log Po/w (WLOGP) : 0.97
Log Po/w (MLOGP) : 0.36
Log Po/w (SILICOS-IT) : 0.87
Consensus Log Po/w : 1.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.17
Solubility : 1.48 mg/ml ; 0.00675 mol/l
Class : Soluble
Log S (Ali) : -1.74
Solubility : 3.95 mg/ml ; 0.018 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.73
Solubility : 4.05 mg/ml ; 0.0185 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 864076-05-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 864076-05-1 ]

* 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 [ 864076-05-1 ]
  • Downstream synthetic route of [ 864076-05-1 ]

[ 864076-05-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 1313196-09-6 ]
  • [ 124-41-4 ]
  • [ 864076-05-1 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: at 20℃; Reflux
Stage #2: at 20℃; for 3 h;
A suspension of 1-(4-bromo-l-methyl-1H-imidazol-2-yl)-2,2,2-trichloroethanone (0.266 g, 868 μιηο, Eq: 1) in methanol (1.11 g, 1.41 ml, 34.7 mmol, Eq: 40) was heated to reflux for 3 hours then at room temperature overnight. To the reaction mixture, sodium methoxide (15.6 mg, 16.1 μ, 86.8 μιηο, Eq: 0.1) was added and stirring was continued at room temperature for 3 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the desired product as a light brown solid (155 mg, 81 percent). MS (m/z) = 219.1, 221.1 [(M+H)+].
68% at 25℃; for 0.333333 h; To the solution of 1.18 g of 1-(-4-bromo-1-methyl-1H-imidazol-2-yl)-2,2,2-trichloroethanone in 10 mL of methanol was added 42 mg of sodium methoxide and the resulting mixture was stirred at 25° C. for 20 min. TLC showed completion of the reaction. The solution was evaporated, redissolved in 30 mL of DCM, washed with water (15 mL.x.2) and brine (15 mL). The solution was dried over anhydrous sodium sulfate and filtered. The residue was purified by silica gel column (DCM/MeOH=60/1) to give 4-bromo-1-methyl-1H-imidazole-2-carboxylic acid methyl ester (0.575 g, yield 68percent). 1H NMR (300 MHz, CDCl3) δ 7.02 (s, 1H), 4.00 (s, 3H). 3.93 (s, 3H). LC-MS calcd for C6H7BrN2O2 (m/e) 217.97, obsd 219 and 221 [M+1]+
Reference: [1] Patent: WO2017/76852, 2017, A1, . Location in patent: Page/Page column 53
[2] Patent: US2012/295885, 2012, A1, . Location in patent: Page/Page column 32
  • 2
  • [ 67-56-1 ]
  • [ 1313196-09-6 ]
  • [ 864076-05-1 ]
YieldReaction ConditionsOperation in experiment
96% at 20℃; for 0.5 h; A solution of SI-2 (1.91 g, 6.24 mmol) and DMAP (305 mg, 2.50 mmol) in MeOH (31 mL) was stirred for 30min at room temperature. The reaction mixture was evaporated and the obtained residue was purified by silica gel column chromatography (SiO2, EtOAc) to give the desired product 6a (1.32 g, 96percent yield) as white solid.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 10, p. 2197 - 2200
  • 3
  • [ 67-56-1 ]
  • [ 30148-23-3 ]
  • [ 864076-05-1 ]
YieldReaction ConditionsOperation in experiment
15.6%
Stage #1: With N-Bromosuccinimide In tetrahydrofuran at -10 - 20℃; for 14 h;
Stage #2: at 75℃; for 1 h;
Step 2To a stirred solution of 2,2,2-trichloro-l-(l-methyl-lH-imidazol-2-yl)ethanone (12.42 g, 54.6 mmol) in THF (40 mL) at -10 0C was added n-bromosuccinimide (6.95 ml, 81.9 mmol). The reaction mixturewas kept at -10 0C for 2 h, warmed to RT with stirring for 12 h and concentrated. The residue was purified with ISCO using straight DCM. The solid obtained was dissolved in MeOH (40 mL), 60percent NaH (80 mg) was added and the reaction mixture heated to 75 0C for 1 h. The reaction mixturewas concentrated and the residue purified with ISCO using 0-10percent EtOAc in DCM to give methyl 4-bromo-l-methyl-lH-imidazole-2- carboxylate (1.86 g, 15.6percent yield).
Reference: [1] Patent: WO2009/75874, 2009, A1, . Location in patent: Page/Page column 132
  • 4
  • [ 30148-23-3 ]
  • [ 864076-05-1 ]
Reference: [1] Patent: US2012/295885, 2012, A1,
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 10, p. 2197 - 2200
[3] Patent: WO2017/76852, 2017, A1,
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