Structure of 698-19-1
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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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CAS No. : | 698-19-1 |
Formula : | C8H10BrN |
M.W : | 200.08 |
SMILES Code : | CNCC1=CC=CC=C1Br |
MDL No. : | MFCD05262953 |
Boiling Point : | No data available |
InChI Key : | TUADRPBKJHMHDH-UHFFFAOYSA-N |
Pubchem ID : | 522360 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 46.72 |
TPSA ? Topological Polar Surface Area: Calculated from |
12.03 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.25 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.98 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.02 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.61 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.51 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.27 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.64 |
Solubility | 0.458 mg/ml ; 0.00229 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.86 |
Solubility | 2.77 mg/ml ; 0.0139 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.1 |
Solubility | 0.016 mg/ml ; 0.0000798 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 |
-6.11 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 |
1.0 |
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 |
0.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* 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 |
---|---|---|
95% | In tetrahydrofuran; at 20℃; for 16h; | Preparation of ferf-butyl 2-bromobenzyl(methyl)carbamate (59). 58 59 A solution of compound 58 (2.0 g, 10.0 mmol) and Boc20 (2.29 g, 10.5 mmol) in THF (40 mL) was stirred at RT for 16 hours. The mixture was then concentrated in vacuo. The crude product was purified by flash column chromatography over silica gel, which was eluted with 10% EtOAc in heptanes, and yielded compound 59 as a colorless oil (2.8 g, 95% yield). 1H NMR (400 MHz, CDCI3) δ 7.54 (d, 1 H), 7.30 (t, 1 H), 7.13 (m, 2 H), 4.53 (br d, 2 H), 2.87 (br s, 3 H), 1.46 (br d, 9 H). |
76.9% | In tetrahydrofuran; at 25℃; for 1h; | [0178] Step A: To a mixture of N-(2-bromophenyl)-N-methylmethanamine (6.50 g, 32.5 mmol, 1 eq .) in THF (R.0 mL) was added B0C2O (R80 g, 35.7 mmol, 8.21 mL, 1,10 eq.) dropwise at 25 C, and the mixture was stirred at 25 C for 1 hour. The reaction mixture was directly concentrated in vacuo to give a residue. The residue was purified by column chromatography (S1O2, petroleum ether/ethyl acetate = 20/1 to 10/1) to give tert-butyl (2-bromobenzyl)(methyl)carbamate (R50 g, 25.0 mmol, 76.9% yield) as a colorless oil. [0179] NMR (400 MHz, CDCb) d 7.55 (br d , J= 8.0 Hz, 1H), 7.34 -7.28 (m, 1H), 7.22-7.08 (m, 2H), 4.61-4.42 (m, 2H), 2.94 -2.78 (m, 3H), 1.60 -1.33 (m, 9H). |
76.9% | In tetrahydrofuran; at 25℃; for 1h; | To a mixture of l-(2-bromophenyl)-N-methylmethanamine (6.50 g, 32.5 mmol, 1 eq.) in THF (70.0 mL) was added B0C2O (7.80 g, 35.7 mmol, 8.21 mL, 1.10 eq.) dropwise at 25 C, and the mixture was stirred at 25 C for 1 hour. The reaction mixture was directly concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 20/1 to 10/1) to give tert- butyl (2- bromobenzyl)(methyl)carbamate (7.50 g, 25.0 mmol, 76.9% yield) as a colorless oil. (0179) [0165] 1H NMR (400 MHz, CDCb) d 7.55 (br d, J= 8.0 Hz, 1H), 7.34 - 7.28 (m, 1H), 7.22 - (0180) 7.08 (m, 2H), 4.61 - 4.42 (m, 2H), 2.94 - 2.78 (m, 3H), 1.60 - 1.33 (m, 9H). |
76.9% | In tetrahydrofuran; at 25℃; for 1h; | To a mixture of 1-(2-bromophenyl)-N-methylmethanamine (6.50 g, 32.5 mmol, 1 eq.) in THF (70.0 mL) was added Boc2O (7.80 g, 35.7 mmol, 8.21 mL, 1.10 eq.) dropwise at 25 C, and the mixture was stirred at 25 C for 1 hour. The reaction mixture was directly concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 20/1 to 10/1) to give tert-butyl (2-bromobenzyl)(methyl)carbamate (7.50 g, 25.0 mmol, 76.9% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.55 (br d, J = 8.0 Hz, 1H), 7.34 - 7.28 (m, 1H), 7.22 -7.08 (m, 2H), 4.61 - 4.42 (m, 2H), 2.94 - 2.78 (m, 3H), 1.60 - 1.33 (m, 9H). |
76.9% | In tetrahydrofuran; at 25℃; for 1h; | To a mixture of 1-(2-bromophenyl)-N-methylmethanamine (6.50 g, 32.5 mmol, 1 eq.) in THF (70.0 mL) was added Boc2O (7.80 g, 35.7 mmol, 8.21 mL, 1.10 eq.) dropwise at 25 C, and the mixture was stirred at 25 C for 1 hour. The reaction mixture was directly concentrated in vacuo to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether/ethyl acetate = 20/1 to 10/1) to give tert-butyl (2-bromobenzyl)(methyl)carbamate (7.50 g, 25.0 mmol, 76.9% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.55 (br d, J = 8.0 Hz, 1H), 7.34 - 7.28 (m, 1H), 7.22 -7.08 (m, 2H), 4.61 - 4.42 (m, 2H), 2.94 - 2.78 (m, 3H), 1.60 - 1.33 (m, 9H). |
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