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CAS No. : | 947248-52-4 | MDL No. : | MFCD09864902 |
Formula : | C7H6BrN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LAUJNLOJYLUKCP-UHFFFAOYSA-N |
M.W : | 212.05 | Pubchem ID : | 44119296 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.3 |
TPSA : | 43.32 Ų |
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) : | -6.1 cm/s |
Log Po/w (iLOGP) : | 1.65 |
Log Po/w (XLOGP3) : | 2.11 |
Log Po/w (WLOGP) : | 1.69 |
Log Po/w (MLOGP) : | 1.27 |
Log Po/w (SILICOS-IT) : | 0.9 |
Consensus Log Po/w : | 1.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.09 |
Solubility : | 0.173 mg/ml ; 0.000814 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.65 |
Solubility : | 0.474 mg/ml ; 0.00224 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.58 |
Solubility : | 0.551 mg/ml ; 0.0026 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.88 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H312-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With water; lithium hydroxide In tetrahydrofuran at 20℃; for 24 h; | Intermediate 6: 6-bromoimidazo[1 ,2-a]pyridin-2 -amine A solution of Λ/-(6-bromoimidazo[1 ,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide (5.5 g, 18.2 mmol) and lithium hydroxide (1.2 g, 27.3 mmol) in THF/Water (5OmL, 7:3) was stirred at room temperature for 24h. THF was then removed under reduced pressure and the aqueous layer was extracted with DCM. Combined organic layers were then washed with brine, dried over sodium sulphate and concentrated under reduced pressure to give the titled compound as a pale brown solid (2.9 g, 77percent). HPLC (X-Terra), Rt: 3.07 min (purity: 97.0percent). LC/MS (Atlantis), M+(ESI): 214.1.1H-NMR (DMSO-d6, 400 MHz) δ 8.58-8.59 (1 H, s), 7.11-7.13 (1 H, d), 7.05-7.07 (1 H, d), 6.98 (1 H1 S), 5.19 (2H, s). |
42% | With methanol; water; potassium carbonate In tetrahydrofuran at 60℃; for 16 h; | Step 4. 6-bromoimidazo[1,2-a]pyridin-2-amine To a 250 mL round-bottomed flask was added N-(6-bromoH-imidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide (3.50 g, 11 mmol), THF (15 mL), methanol (15 mL), water (15 mL) and potassium carbonate (16 g, 114 mmol). The mixture was stirred at 60° C. for 16 h. After cooling to rt, the mixture was poured into water (100 mL) and extracted with CH2Cl2 (4*75 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (0.5 to 5.0percent MeOH/CH2Cl2) afforded the title compound (1.01 g, 42percent). MS (ESI, positive ion) m/z: 212 (M(79Br)+1). |
8.3 g | With sodium hydroxide In ethanol at 80℃; | A mixture of A81-3 (15 g, crude, 46 mmol) in 1 N NaOH/EtOH (50 mL/40 mL) was stirred at 80°C overnight. After cooled to r.t., the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Na2S04 and the solvent was removed by vacuum. The residue was recrystallized in petroleum ether to give a brown solid (8.3 g, 85percent). H NMR (400 MHz, DMSO-d<5) δ 8.60 (s, 1H), 7.32 -7.05 (m, 2H), 7.00 (s, 1H), 5.22 (s, 2H). |
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