Structure of 30951-66-7
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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. : | 30951-66-7 |
Formula : | C9H11BrO |
M.W : | 215.09 |
SMILES Code : | CC(O)(C1=CC=CC(Br)=C1)C |
MDL No. : | MFCD11870097 |
InChI Key : | ZRFMJMFYMQAUDO-UHFFFAOYSA-N |
Pubchem ID : | 15072383 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.33 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 49.77 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.44 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.75 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.57 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.91 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.69 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.67 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.24 |
Solubility | 0.123 mg/ml ; 0.000571 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.83 |
Solubility | 0.318 mg/ml ; 0.00148 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.5 |
Solubility | 0.0674 mg/ml ; 0.000313 mol/l |
Class? Solubility class: Log S scale |
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 |
-5.66 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) |
1.34 |
* 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 |
---|---|---|
93% | EXAMPLE 76; Preparation of N- [ (lS, 2R)-3- { [l- (3-bromophenyl)-l- methylethyl] amino}-1- (3, 5-difluorobenzyl)-2-hydroxypropyl] acetamide; 32 Scheme 8 O Br MeMgBr g NaN3 Br 'H Bu OMe OH Nh THF TFA THF 4 | kOH SOH 4 reflux H 19 H HOH H N, 1) TFA-0 zon F F 0 HCI 2) Ac-Im F 31 3) HCI 30 30 F 31 F NaOH HOH H Bu F 32 Step 1; Preparation of 2- (3-bromophenyl)-2-propanol 27; To 75 mmol of methylmagnesium bromide in 25 mL of ether stirring at 6 C is added, dropwise over 10 min, a solution of methyl-3-bromobenzoate (4.3 g, 20 mmol) in 25 mL of dry THF. The mixture is then allowed to warm to ambient temperature and stirred for 3.5 h, then cooled to 0C and quenched by dropwise addition of aqueous 10% HC1. The acidified mixture is extracted twice with ethyl acetate, and the combined organic phases are washed with 1 N NaHC03 and with brine. The solution is dried over Na2SO4, concentrated, and chromatographed over silica gel, eluting with 15% ethyl acetate in heptane, to afford 4.00 g (18.6 mmol, 93%) of 2- (3-bromophenyl)-2- propanol 27 as a pale yellow oil | |
80% | In tetrahydrofuran; at 0 - 20℃; for 4h; | General procedure: To a solution of 26 (7.41 mmol) in anhydrous tetrahydrofuran (30 mL) was added 3M methyl magnesium bromide (22.24 mmol) dropwise at 0 C. The mixture was stirred for 4 hours at rt and quenched with saturated NH4Cl solution at 0. The reaction mixture was partitioned between water (50 mL) and ether (30 mL×3). The organic phase was dried with anhydrous Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel to give the product. |
10% | In tetrahydrofuran; at 20℃; for 2h;Cooling with ice; | Methyl 3-bromobenzoate (2g, 9.30mmol)Dissolved in anhydrous tetrahydrofuran (30mL),Add methylmagnesium bromide dropwise under ice bath conditions(1M in THF, 11.6mL, 11.6mmol),The reaction was then reacted at room temperature for two hours and then quenched with saturated ammonium chloride solution.After extraction with ethyl acetate, the organic phases were combined, and the organic phases were washed with saturated brine and dried with anhydrous sodium sulfate. The solvent was evaporated to dryness under reduced pressure and column chromatography was used to obtain the target compound 39b (0.2 g, 10%). |
2- (3-Bromo-phenyl)-propan-2-ol :; The 3-bromo-benzoic acid methyl ester (1.0 g, 4.7 mmol) in tetrahydrofuran (10 mL) was brought to-78 C followed by the addition of methyl magnesium bromide (7.7 mL, 10.81 mmol) and warmed to room temperature and stirred for 17 h. The mixture was poured into sat NH4Cl and extracted with ethylacetate. The organic extracts were combined, washed with brine, dried over magnesium sulfate and chromatographed on silica gel using 04% methanol/dichloromethane to afford colorless oil. | ||
14.9 g | In tetrahydrofuran; diethyl ether; at -78 - 20℃; for 2h; | To a solution of <strong>[618-89-3]methyl 3-bromobenzoate</strong> (15.0 g, 69.8 mmol) in THF (140 mL) at -78 C was added dropwise a solution of MeMgBr/diethyl ether [3.0M] (58 mL). The reaction mixture was warmed up to room temperature and stirred for 2 h. The solution was poured to an aqueous saturated solution of ammonium chloride and the organic material was extracted with EtOAc. The organic layer was dried over Na2S04, filtered and concentrated to afford the corresponding alcohol (14.9 g) which was used without further purification. |
14.9 g | In tetrahydrofuran; diethyl ether; at -78 - 20℃; for 2h; | To a solution of <strong>[618-89-3]methyl 3-bromobenzoate</strong> (15.0 g, 69.8 mmol) in THF (140 mL) at -78 C. was added dropwise a solution of MeMgBr/diethyl ether [3.0M] (58 mL). The reaction mixture was warmed up to room temperature and stirred for 2 h. The solution was poured to an aqueous saturated solution of ammonium chloride and the organic material was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated to afford the corresponding alcohol (14.9 g) which was used without further purification. |
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