73101-74-3|2-(Bromomethyl)benzo[d]oxazole| Ambeed

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Structure of 73101-74-3

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Quality Control of [ 73101-74-3 ] Purity: 98% SDS Specification

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Product Details of [ 73101-74-3 ]

CAS No. :	73101-74-3
Formula :	C₈H₆BrNO
M.W :	212.04
SMILES Code :	BrCC1=NC2=CC=CC=C2O1
MDL No. :	MFCD11856915
InChI Key :	VVKQNCHUKOHTDO-UHFFFAOYSA-N
Pubchem ID :	12745944

Safety of [ 73101-74-3 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H314
Precautionary Statements:	P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405
Class:	8
UN#:	1759
Packing Group:	Ⅱ

Computational Chemistry of [ 73101-74-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.12
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	46.85
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.03 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.23
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.6
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.57
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.79
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.89
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.42

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.33
Solubility	0.0987 mg/ml ; 0.000465 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.8
Solubility	0.339 mg/ml ; 0.0016 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.18
Solubility	0.0141 mg/ml ; 0.0000664 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

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) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.75 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.41

Application In Synthesis of [ 73101-74-3 ]

* 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.

Downstream synthetic route of [ 73101-74-3 ]

[ 73101-74-3 ] Synthesis Path-Downstream 1~35

1
[ 95-21-6 ]
[ 73101-74-3 ]

Yield	Reaction Conditions	Operation in experiment
70%		a 2-Bromomethylbenzoxazole Following the procedure of Example 4(a), except using 2-methylbenzoxazole in place of 2-methylbenzothiazole, the title compound (2.22 g, 70%) was prepared as a yellow oil: 1 H NMR (250 MHz, DMSO-d6) delta 5.17 (s, 2H), 7.55 (m, 2H), 8.01 (d, J=7.9, 1.8 Hz, 1H), 8.20 (dd, J=7.9, 1.8 Hz, 1H).
45%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 12.0h;Reflux;	Under stirring, to a solution of 2-methylbenzoxazole (665 mg, 5 mmol) in carbon tetrachloride (16 mL), Add N-bromosuccinimide (890 mg, 5 mmol) Azoisobutyronitrile (188 mg, 1.15 mmol) and the mixture was stirred at reflux for 12 h. Cooled, filtered, and the filtrate was concentrated and the residue was chromatographed to give the title compound as a pale yellow oil (471 mg, yield 45%).
17%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Heating / reflux;	A solution of 35 g (0.263 mol) of 2-methyl-benzooxazole in CC14 (300 mL) was treated with 47 g (0.263, 1 eq) of NBS and 1 g of benzoyl peroxide. The mixture was refluxed (100C) over night then cooled. Succinimide was filtered off and the mixture was evaporated to dryness. Column chromatography yielded 9.2 g (17%) of 2-bromomethyl- benzooxazole as a light yellow oil, MS: 210,212 (MH+). (H. Uno, M. Kurokawa, Y. Masuda, Chem. Pharm. Bull., 1981,29, 2359).

References: [1]Patent: US5977101,1999,A .
[2]Patent: CN103570683,2018,B .Location in patent: Paragraph 0255; 0260; 0261.
[3]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 2359 - 2361.
[4]Patent: WO2005/92856,2005,A1 .Location in patent: Page/Page column 95.

2
[ 73101-74-3 ]
[ 138129-45-0 ]
[ 138128-87-7 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 457 - 465.

3
[ 73101-74-3 ]
[ 73535-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium sulfite; In methanol; water;	EXAMPLE 5 Various compounds of the formula: STR10 as listed in the following Table 4 were prepared in substantially the same manner as in Examples 3 and 4. example 6 benzoxazole-2-methanesulfonyl chloride: To a solution of 3.0 g of <strong>[73101-74-3]2-<strong>[73101-74-3]bromomethylbenzoxazole</strong></strong> [prepared according to the procedures described in Belgian Pat. No. 624,463] in 40 ml of methanol was added a solution of 1.9 g of sodium sulfite in 40 ml of water. The mixture was heated with stirring at 60 C. for 6 hours and concentrated under reduced pressure to give crude sodium benzoxazole-2-methanesulfonate (4.5 g).

References: [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 2359 - 2361.
[2]Patent: US4172896,1979,A .

4
[ 141-97-9 ]
[ 73101-74-3 ]
2-Benzooxazol-2-ylmethyl-3-oxo-butyric acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 617 - 628.

5
[ 73101-74-3 ]
[ 136694-17-2 ]
3-[5-(benzooxazol-2-ylmethoxy)-3-tert-butylsulfanyl-1-(4-chloro-benzyl)-1H-indol-2-yl]-2,2-dimethyl-propionic acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2391 - 2396.

6
[ 73101-74-3 ]
[ 335665-38-8 ]
[ 335665-42-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 309 - 312.

7
[ 73101-74-3 ]
3-[5-(benzooxazol-2-ylmethoxy)-3-tert-butylsulfanyl-1-(4-chloro-benzyl)-1H-indol-2-yl]-2,2-dimethyl-propionic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2391 - 2396.

8
[ 73101-74-3 ]
[ 73101-70-9 ]