[ CAS No. 29579-11-1 ] {[proInfo.proName]}

Name: 29579-11-1|2-(Benzyloxy)benzamide|95+%
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SKU: A833545
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Quality Control of [ 29579-11-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 29579-11-1 ]

SDS Specification

Alternatived Products of [ 29579-11-1 ]

Product Details of [ 29579-11-1 ]

CAS No. :	29579-11-1	MDL No. :	MFCD00025471
Formula :	C₁₄H₁₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HHKNJUHXNDIVFN-UHFFFAOYSA-N
M.W :	227.26	Pubchem ID :	296051
Synonyms :

Calculated chemistry of [ 29579-11-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	65.52
TPSA :	52.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.86
Log Po/w (XLOGP3) :	1.66
Log Po/w (WLOGP) :	2.21
Log Po/w (MLOGP) :	2.39
Log Po/w (SILICOS-IT) :	2.55
Consensus Log Po/w :	2.13

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.55
Solubility :	0.636 mg/ml ; 0.0028 mol/l
Class :	Soluble
Log S (Ali) :	-2.37
Solubility :	0.964 mg/ml ; 0.00424 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.66
Solubility :	0.00501 mg/ml ; 0.000022 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.82

Safety of [ 29579-11-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 29579-11-1 ]

* 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 [ 29579-11-1 ]

[ 29579-11-1 ] Synthesis Path-Downstream 1~31

1
[ 100-39-0 ]
[ 65-45-2 ]
[ 29579-11-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium carbonate; In acetone; for 16h;Heating / reflux;	To a solution of 2-hydroxybenzamide (2.74 g, 20 mmol, 1.0 equiv) and K2CO3 (3.30 g, 24 mmol, 1.2 equiv) in acetone (100 mL) was added benzyl bromide (2.80 mL, 24 mmol, 1.2 equiv) and the reaction heated at reflux for 16 hours. After cooling to room temperature, the solution was filtered and the filtrate was concentrated under reduced pressure. The crude solid was recrystallized from acetone to afford the title compound (2.89 g, 62%) as a white solid: 1H NMR (CDCl3, 600 MHz) delta 5.19 (s, 2H), 5.92 (br s, 1H), 7.05-7.10 (m, 2H), 7.36-7.48 (m, 6H), 7.73 (br s, 1H), 8.23 (d, J=7.8 Hz, 1H); 13C NMR (CDCl3, 150 MHz) delta 71.5, 112.9, 121.3, 121.8, 128.1, 129.0, 129.2, 132.9, 133.6, 135.8, 157.4, 167.2; HRMS (APCI+) calcd for C14H14NO2 [M+H]+ 228.1019, found 228.1042 (error 10.0 ppm).

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3088 - 3100
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 6080 - 6094
[3]Patent: US2008/293666,2008,A1 .Location in patent: Page/Page column 41
[4]Journal of the American Pharmaceutical Association (1912),1956,vol. 45,p. 514,517

2
[ 29579-11-1 ]
[ 53-86-1 ]
2-Benzyloxy-N-{2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetyl}-benzamide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1980,vol. 30,p. 1314 - 1325

4
[ 100-44-7 ]
[ 65-45-2 ]
[ 29579-11-1 ]

Yield	Reaction Conditions	Operation in experiment
21%	With potassium carbonate; potassium iodide; In acetone; for 18h;Reflux;	To amide15(0.80 g, 5.83 mmol), K2CO3(0.97 g, 7.02 mmol) and KI (1.17 g, 7.02 mmol) in acetone (30 mL) was added benzyl chloride (0.81 mL, 7.02 mmol), and the reaction stirred at reflux for 18 h. The solution was cooled and filtered and solvent removed in vacuo. The crude product was recrystallised from acetone to yield6(0.28 g, 21%) as a cream solid, mp 112-114 C (lit. [58] mp 115-116 C). deltaH(CDCl3) 8.25 (1H, dd,J= 7.8, 1.8 Hz, H-6), 7.73 (1H, br s, NH), 7.50-7.37 (6H, m, Ar-H), 7.13-7.06 (2H, m, Ar-H), 5.81 (1H, br s, NH), 5.20 (2H, s, CH2). deltaC(CDCl3) 167.1 (C = O), 157.3 (C), 136.8 (C), 133.6 (CH), 132.9 (CH), 129.2 (2 × CH), 128.9 (CH), 128.1 (2 × CH), 121.7 (CH), 121.3 (C), 112.9 (CH), 71.5 (CH2). LRMSm/z228.2 (100%, M + H). HPLC purity: 100%. These data are in good agreement with literature values [59]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1971 - 1974
[2]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 1537 - 1544
[3]Molecules,2019,vol. 24

5
[ 29579-11-1 ]
[ 109604-76-4 ]

Yield	Reaction Conditions	Operation in experiment
	With H2;Pd on carbon; In methanol; 1-bromo-2,2-dimethoxyethane; acetic acid;	PREPARATION 10 2-(Oxazol-2-yl)-phenol <strong>[29579-11-1]2-Benzyloxybenzamide</strong> (2.0 g, 8.8 mmol) was heated to about 130 C. in bromoacetaldehyde dimethylacetal (10 mL, 85 mmol) under N2 (g) for 3.5 hours. Although pure 2-(2-benzyloxyphenyl)oxazole could be obtained by recrystallization from CHCl3 /CCl4, the entire mixture was usually directly hydrogenated using 10% Pd on carbon (600 mg) at 40 psi of H2 in 1% HOAc in MeOH (100 mL). Following removal of catalyst by filtration and concentration of the filtrate in vacuo the residue was chromatographed on silica (10?5% acetone/hexanes) to afford 2-(oxazol-2-yl)phenol (860 mg; GC-MS m/z 161 (M+)).

Reference： [1]Patent: US6130217,2000,A

6
[ 29579-11-1 ]
2-benzyloxybenzylamine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; In water;	EXAMPLE 16 Analogously to Example 3, by debenzylation of 18 g of crude 1-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)ethylbenzylamino]-3-[2-[N'-(2-hydroxyethyl)ureidomethyl]phenoxy]-propan-2-ol, after crystallisation from dimethylformamide/ether 1-[2-(3-carbamoyl-4-hydroxyphenoxy)ethylamino]-3-[2-[N'-(2-hydroxyethyl)ureidomethyl]phenoxy]propan-2-ol is obtained having a melting point of 164-166. The starting material can be prepared as follows: 2-benzyloxybenzylamine: In a Soxhlet apparatus 18.4 g of lithium aluminium hydride in 1800 ml of dry ether are boiled under a nitrogen atmosphere at a bath temperature of 70, 5.3 g of <strong>[29579-11-1]2-benzyloxybenzamide</strong> being introduced into the Soxhlet thimble. After 21 hours the reaction mixture is immersed in an ice bath, and 18.4 ml of water, 18.4 ml of 15% sodium hydroxide solution and 55 ml of water are added dropwise in succession, whilst stirring. The temperature may be allowed to rise to a maximum of +10. Stirring of the mixture is then continued at 20 and the resulting precipitate is suction-filtered and washed with ether. The filtrate is concentrated by evaporation in vacuo and the oil remaining is stirred with 500 ml of 10% hydrochloric acid and 400 ml of ether for 2 hours, whilst cooling with ice. The precipitated 2-benzyloxybenzylamine hydrochloride is suction-filtered, washed with water and ether and dried in vacuo. Melting point 190-191. 2-benzyloxybenzyl isocyanate:
	With hydrogenchloride; sodium hydroxide; In water;	2-benzyloxybenzylamine In a Soxhlet apparatus 18.4 g of lithium aluminium hydride in 1800 ml of dry ether are boiled under a nitrogen atmosphere at a bath temperature of 70, 5.3 g of <strong>[29579-11-1]2-benzyloxybenzamide</strong> being introduced into the Soxhlet thimble. After 21 hours the reaction mixture is immersed in an ice bath, and 18.4 ml of water, 18.4 ml of 15% sodium hydroxide solution and 55 ml of water are added dropwise in succession, whilst stirring. The temperature may be allowed to rise to a maximum of +10. Stirring of the mixture is then continued at 20 and the resulting precipitate is suction-filtered and washed with ether. The filtrate is concentrated by evaporation in vacuo and the oil remaining is stirred with 500 ml of 10% hydrochloric acid and 400 ml of ether for 2 hours, whilst cooling with ice. The precipitated 2-benzyloxybenzylamine hydrochloride is suction-filtered, washed with water and ether and dried in vacuo. Melting point 190-191.

Reference： [1]Patent: US4727067,1988,A
[2]Patent: US4497813,1985,A

7
[ 873556-45-7 ]
[ 79-37-8 ]
[ 29579-11-1 ]
[ 939794-38-4 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 6080 - 6094

8
[ 29579-11-1 ]
[ 65-45-2 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 4817 - 4819

9
[ 75-44-5 ]
[ 29579-11-1 ]
C₁₅H₁₂ClNO₃*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In Dichlorodifluoromethane; at 50℃; for 3h;	To a stirred solution of <strong>[29579-11-1]2-benzyloxybenzamide</strong> (114 mg, 0.50 mmol, 1.0 equiv) in CH2Cl2 (20 mL) (COCl)2 (129 muL, 1.5 mmol, 3 equiv) was added dropwise at room temperature. The solution was then heated at 50 C. for 3 hours. After cooling to room temperature, the reaction was concentrated in vacuo to afford a light yellow solid. Next, a solution of 5'-amino-N6-tert-butoxycarbonyl-5'-deoxy-2',3'-O-isopropylideneadenosine (244 mg, 0.6 mmol, 1.2 equiv) in CH3CN (10 mL) was added and the resulting mixture was stirred 16 hours at room temperature. The crude reaction was concentrated in vacuo and the residue was partitioned between CH2Cl2 (25 mL) and H2O (25 mL). The aqueous layer was extracted with CH2Cl2 (2×25 mL). The combined organic extracts were dried (Na2SO4) and concentration under reduced pressure. Purification by flash chromatography (7:3 EtOAc/hexanes) afforded the title compound (290 mg, 88%) as a white solid: Rf 0.1 (60:40 EtOAc/hexane); 1H NMR (CDCl3, 600 MHz) delta 1.35 (s, 3H), 1.54 (s, 9H), 1.59 (s, 3H), 3.64-3.71 (m, 2H), 4.41-4.44 (m, 1H), 4.99 (dd, J=6.0, 3.6 Hz, 1H), 5.28 (s, 2H), 5.37 (dd, J=6.0, 3.0 Hz, 1H), 6.12 (d, J=3.0 Hz, 1H), 7.05 (d, J=8.4 Hz, 1H), 7.10 (t, J=7.8 Hz, 1H), 7.35-7.37 (m, 1H), 7.40-7.43 (m, 4H), 7.48 (dt, J=8.4, 1.2 Hz, 1H), 8.05 (br s, 1H, NH), 8.12 (dd, J=7.8, 1.2 Hz, 1H), 8.18 (s, 1H), 8.74 (s, 1H), 8.85 (t, J=6.0 Hz, 1H, NH), 9.97 (s, 1H, NH); 13C NMR (CDCl3, 150 MHz) delta 25.7, 27.5, 28.3, 41.5, 71.8, 81.9, 82.5, 84.2, 85.3, 90.4, 113.5, 115.2, 119.9, 122.1, 122.3, 127.7, 129.1, 129.2, 132.9, 134.9, 135.0, 141.7, 149.7, 150.2, 150.7, 153.4, 153.9, 157.2, 165.9; HRMS (ESI+) calcd for C33H38N7O8 [M+H]+ 660.2776, found 660.2667 (error 16.5 ppm).

Reference： [1]Patent: US2008/293666,2008,A1 .Location in patent: Page/Page column 41

10
[ 29579-11-1 ]
[ 131056-82-1 ]
[ 1186372-33-7 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5295 - 5298

11
[ 74511-44-7 ]
[ 29579-11-1 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5295 - 5298

12
[ 2725-60-2 ]
[ 29579-11-1 ]
[ 1201915-05-0 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 152 - 161

13
[ 29579-11-1 ]
[ 90965-06-3 ]
[ 1201914-97-7 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 152 - 161

14
[ 79-37-8 ]
[ 29579-11-1 ]
[ 589-16-2 ]
[ 1369525-79-0 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3088 - 3100

15
[ 29579-11-1 ]
[ 1369525-69-8 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3088 - 3100

16
[ 3381-87-1 ]
[ 29579-11-1 ]