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[ CAS No. 766-55-2 ] {[proInfo.proName]}

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Chemical Structure| 766-55-2
Chemical Structure| 766-55-2
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Product Details of [ 766-55-2 ]

CAS No. :766-55-2 MDL No. :MFCD07782103
Formula : C6H5N3 Boiling Point : -
Linear Structure Formula :- InChI Key :VTVRXITWWZGKHV-UHFFFAOYSA-N
M.W : 119.12 Pubchem ID :136599
Synonyms :

Calculated chemistry of [ 766-55-2 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 32.99
TPSA : 30.19 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) : -6.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.35
Log Po/w (XLOGP3) : 0.33
Log Po/w (WLOGP) : 0.73
Log Po/w (MLOGP) : 0.56
Log Po/w (SILICOS-IT) : 0.58
Consensus Log Po/w : 0.71

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.53
Solubility : 3.54 mg/ml ; 0.0298 mol/l
Class : Very soluble
Log S (Ali) : -0.53
Solubility : 35.3 mg/ml ; 0.297 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.66
Solubility : 2.59 mg/ml ; 0.0218 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 766-55-2 ]

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 [ 766-55-2 ]

* 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 [ 766-55-2 ]
  • Downstream synthetic route of [ 766-55-2 ]

[ 766-55-2 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 6775-78-6 ]
  • [ 766-55-2 ]
YieldReaction ConditionsOperation in experiment
87% With palladium on activated charcoal; hydrogen; triethylamine In tetrahydrofuran; methanol for 16 h; To a stirred solution of 6-chloroimidazo[1,2-bjpyridazine (800 mg, 5.21 mmol) in methanol (20 mL) and tetrahydrofuran (20 mL) was added triethylamine (0.8 mL, 5.74mmol) followed by Pd/C (100 mg, 0.094 mmol). The mixture was stirred under hydrogen atmosphere for 16h. The reaction mixture was filtered through celite and the celite bed was washed with methanol. The combined filtrate was concentrated then suspended in water and extracted with ethyl acetate (3x). The organic layer was dried over Na2SO4 and filtered to give the imidazo[1,2-bjpyridazine (550 mg, 87percent) as off white solid. LCMS[m/z 120 (M+H)j; ‘H NMR (300 MHz, DMSO-d6) ö 8.51 (dd, J4.53, 1.51 Hz, 1H) 8.29(d,J0.76Hz, 1 H) 8.05-8.19(m, 1 H)7.79(d,J1.13 Hz, 1 H) 7.22 (dd,J=9.44,4.53 Hz, 1 H).
Reference: [1] Patent: WO2016/210036, 2016, A1, . Location in patent: Page/Page column 106; 107
  • 2
  • [ 5469-70-5 ]
  • [ 107-20-0 ]
  • [ 766-55-2 ]
Reference: [1] Patent: CN105218551, 2016, A, . Location in patent: Paragraph 0024
[2] Patent: CN105218550, 2016, A, . Location in patent: Paragraph 0025
  • 3
  • [ 6653-91-4 ]
  • [ 766-55-2 ]
Reference: [1] Synlett, 2008, # 9, p. 1279 - 1282
  • 4
  • [ 1044276-48-3 ]
  • [ 766-55-2 ]
Reference: [1] Synlett, 2008, # 9, p. 1279 - 1282
  • 5
  • [ 766-55-2 ]
  • [ 18087-73-5 ]
YieldReaction ConditionsOperation in experiment
75% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chloroform for 2 h; Reflux The imidazo [1,2-b] pyridazine (6.0g, 50 . 4mmol), NBS (6.0g, 75 . 6mmol) and a catalytic amount of AIBN is added to the 50 ml chloroform, heating to reflux the reaction 2 hours, TLC detection of the reaction process, the raw materials of the reaction after cooling to room temperature stirring under the conditions of the ice bath, a precipitate out, filtered and the filtrate concentrated to get the pure product.The pure product as a pale yellow solid, yield: 75percent
75% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chloroform for 2 h; Reflux The imidazo [1,2-b] pyridazine (6.0 g, 50.4 mmol), NBS (6.0 g, 75.6 mmol) and a catalytic amount of AIBN were added to 50 mL of chloroform and the reaction was heated to reflux for 2 hours, The reaction solution was cooled to room temperature when the raw material disappeared with the TLC detection of the reaction process, and a precipitate precipitated after the solution stirred in an ice bath. After filtering, the filtrate concentrated under reduced pressure to give the pure product. A pale yellow solid, yield: 75percent. 1H NMR (CDCl3, 400 MHz, δ ppm): 8.50 (d, J = 3.6 Hz, 1H), 8.01-7.98 (m, 1H), 7.84 (s, 1H), 7.15-7.12 (m, 1H). ESI-MS m/z : 200.1 [M+H]+.
74% With N-Bromosuccinimide In chloroform for 0.5 h; Reflux Example 15 -4 Synthesis of 3-bromo-imidazo[1,2-b]pyridazine
To imidazo[1,2-b]pyridazine 1*b (10 g) stirring in chloroform (250 ml) was added N-bromosuccinimide (15.7 g) at 5 °C.
The cooling bath was removed and the reaction was heated to reflux which was maintained for 30 minutes.
After leaving to cool overnight the reaction mixture was concentrated under reduced pressure.
The residue was redissolved in ethyl acetate (500 ml), washed with potassium carbonate solution (3 x 200 ml) then brine (100 ml).
The organic extract was dried with magnesium sulphate and concentrated in vacuo to give 3-bromo-imidazo[1,2-b]pyridazine 2*b, 12.3 g (74percent).
1H-NMR (400MHz, DMSO-D6) : δ = 8.68 (1 H, d, 4.4 Hz, ArH), 8.20 (1 H, d, 9.2 Hz, ArH), 7.95 (1 H, s, ArH), 7.33 (1 H, q, 3.4 Hz, ArH).
36% at 0 - 20℃; for 1 h; To a stirred solution of imidazo[1,2-bjpyridazine (200 mg, 1.679 mmol) in acetic acid (10 mL) was added bromine (0.2 mL, 3.88 mmol) at 0 °C. The reaction mixture was allowed to warm to room temperature and stir for 1 hr. The reaction mixture was neutralized with iN sodium hydroxide, poured into EtOAc (20 mL) and 10percent NaHCO3 solution. The layers were separated and the aqueous layer extracted with EtOAC (3x20ml). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated to give 3-bromoimidazo[1,2-bjpyridazine (120 mg, 36percent) as light brown solid. ‘H NMR (400 MHz, DMSO-d6) ö 8.68 (dd, J=4.52, 1.51 Hz, 1 H) 8.19 (dd, J=9.54, 1.51 Hz, 1 H) 7.94 (s, 1 H) 7.28-7.39 (m, 1 H).
9.9 g With N-Bromosuccinimide In chloroform for 0.5 h; Reflux theImidazo [1,2-b] pyridazin(50mmol) dissolved in Chloroform (50 ml), Bromosuccinimide(55 mmoles) was slowly added into the reaction . at reflux System was stirredfor 30 minutes. After cooling to room temperature, the pH was adjusted to 8-9 usingsaturated aqueous sodium carbonatesolution and extracted with ethyl acetate. The extract was washed with water andsaturated brine. After dried overanhydrous sodium sulfate and concentrated to give 9.9 g of the title compound.
9.9 g With N-Bromosuccinimide In chloroform for 0.5 h; Reflux The imidazo [l, 2_b] pyridazine ¢ .0 g, 50 mmol) was dissolved in chloroform (50 ml), N- bromobutyrate ni imide (NBS) (9.8 g, 55 mmol mol) was slowly added thereto.Was refluxed for 30 minutes.After cooling to room temperature, the PH value was adjusted to 8-9 with saturated sodium carbonate solution, extracted with ethyl acetate.The extract was washed with water, brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound 9.9 g.

Reference: [1] Patent: CN105418615, 2016, A, . Location in patent: Paragraph 0079 ; 0080 ; 0081; 0082; 0083; 0084
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 23, p. 5830 - 5835
[3] Patent: EP2818471, 2014, A1, . Location in patent: Paragraph 0122; 0123
[4] Synthesis, 1981, # 12, p. 987 - 989
[5] Patent: WO2016/210036, 2016, A1, . Location in patent: Page/Page column 107
[6] Patent: WO2010/83145, 2010, A1, . Location in patent: Page/Page column 38-39
[7] Patent: US2014/343282, 2014, A1, . Location in patent: Paragraph 0074; 0086
[8] Patent: CN103130792, 2016, B, . Location in patent: Paragraph 0326-0328
[9] Patent: CN103130791, 2016, B, . Location in patent: Paragraph 0288-0290
[10] Patent: CN105218551, 2016, A, . Location in patent: Paragraph 0024
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