Structure of 847906-27-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 847906-27-8 |
Formula : | C8H7IN2 |
M.W : | 258.06 |
SMILES Code : | CC1=CC=CC2=C1NN=C2I |
MDL No. : | MFCD07781632 |
InChI Key : | WYUIOANIHMLVPU-UHFFFAOYSA-N |
Pubchem ID : | 12159606 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 53.78 |
TPSA ? Topological Polar Surface Area: Calculated from |
28.68 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.59 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.6 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.48 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.61 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.44 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.55 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.68 |
Solubility | 0.0535 mg/ml ; 0.000207 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.85 |
Solubility | 0.363 mg/ml ; 0.00141 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.25 |
Solubility | 0.0144 mg/ml ; 0.000056 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.03 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.02 |
* 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 |
---|---|---|
92% | With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 4h; | A solution of 7-methyl-1H-indazole (2 g, 15.15 mmoL), KOH (2.12 g, 37.88 mmoL) and ?2 (7.7 g, 30.3 mmoL) in DIVIF (40 mL) was stirred at room temperature for 4 hrs. The reaction mixture was poured into H20 (200 mL) and extracted with EA (200 mL). The EA layer was washed with saturated NaSO3 (100 mL), H20 (200 mL), brine (200 mL), dried over Na2SO4 and concentrated to give 3-iodo-7-methyl-1H-indazole (3.6 g, yield: 92%) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | General procedure: 5-Chloro-3-iodo-indazole (1.0 g, 3.6 mmol) was stirred in DMF (8 mL) at 0 C. under N2. NaH (60%, 159 mg, 3.96 mmol) was added, and the reaction stirred 45 min. Iodomethane (260 muL, 4.14 mmol) was added, and the reaction stirred 45 min while warming to rt. The solution was quenched with MeOH and concentrated. Purification by silica gel chromatography (10%-40% EtOAc/hexanes gave two isomers: 5-chloro-3-iodo-1-methyl-1H-indazole (740 mg, 70%) was isolated as the major isomer eluting first. 1H NMR (400 MHz, CDCl3): delta 4.09 (3H, s), 7.30 (1H, d, J=8.9 Hz), 7.39 (1H, dd, J=8.9, 1.6 Hz), 7.47 (1H, d, J=1.6 Hz). [M+H] calc'd for C8H6ClIN2, 293, 295. found 293, 295. 5-chloro-3-iodo-2-methyl-2H-indazole (268 mg, 25%) was isolated as the minor isomer eluting second. 1H NMR (400 MHz, CDCl3): delta 4.24 (3H, s), 7.24 (1H, dd, J=9.1, 2.0 Hz), 7.38 (d, 1H, J=1.9 Hz), 7.59 (1H, d, J=9.1 Hz). [M+H] calc'd for C8H6ClN2, 293, 295. found 293, 295. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | To a solution of <strong>[847906-27-8]3-iodo-7-methyl-1H-indazole</strong> (3.6 g, 13.9 mmoL) in DMF (20 mL) was added NaH (670 mg, 16.68 mmoL) at 0 C and the mixture was stirred at room temperature for 40 mins under N2 atmosphere (balloon). Then Mel (1.04 ml, 16.68 mmoL) was added into the reaction mixture and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into H20 (100 mL) and extracted with EA (100 mL). The EA layer was washed with H20 (100 mL), brine (100 mL), dried over Na2SO4 and concentrated to dryness in vacuum. The residue was purified by silica flash column (9% EA in PE) to give 3-iodo-1,7-dimethyl-1H-indazole (2.663 g, yield: 70%) as a yellow solid. ?H NIVIR (400 IVIHz, CDC13): oe = 7.28 (t, J = 8.0 Hz, 1H), 7.13 (d, J = 7.2 Hz, 1H), 7.06 (t, J 7.6 Hz, 1H), 4.32 (s, 3H), 2.74 (s, 3H). MS: m/z 273.1 (M+H). |