[ CAS No. 720720-60-5 ] {[proInfo.proName]}

Name: 720720-60-5|4-(3-Oxomorpholino)benzoic acid|95%
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SKU: A776221
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Quality Control of [ 720720-60-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 720720-60-5 ]

SDS Specification

Alternatived Products of [ 720720-60-5 ]

Product Details of [ 720720-60-5 ]

CAS No. :	720720-60-5	MDL No. :	MFCD13176569
Formula :	C₁₁H₁₁NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HUZZDKHRFFOLQU-UHFFFAOYSA-N
M.W :	221.21	Pubchem ID :	23087789
Synonyms :

Calculated chemistry of [ 720720-60-5 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.27
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	59.33
TPSA :	66.84 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.51
Log Po/w (XLOGP3) :	0.46
Log Po/w (WLOGP) :	0.37
Log Po/w (MLOGP) :	0.48
Log Po/w (SILICOS-IT) :	0.99
Consensus Log Po/w :	0.76

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.65
Solubility :	4.99 mg/ml ; 0.0226 mol/l
Class :	Very soluble
Log S (Ali) :	-1.43
Solubility :	8.18 mg/ml ; 0.037 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.85
Solubility :	3.1 mg/ml ; 0.014 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 720720-60-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:	N/A
Hazard Statements:	H302-H312-H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 720720-60-5 ]

* 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 [ 720720-60-5 ]

[ 720720-60-5 ] Synthesis Path-Downstream 1~17

1
[ 766556-56-3 ]
[ 720720-60-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium hydroxide; In methanol; water; for 1h;	General procedure: Compound 101 5a (3.0g, 12.1mmol) was dissolved in 109 methanol (36mL). To the solution was added 1M 110 NaOH (5mL), and the reaction mixture was stirred at room temperature for 1h. The mixture was adjusted to pH 5 with 1M hydrochloric acid. The resulting precipitate was filtered, washed with H2O/EtOH (6mL, v/v, 2:1), and dried to afford the desired 111 product which was pure enough for the next step (2.4g, 90%).
		The product from Part B (0.50 g, 2.0 mmol) was stirred in ETOH (10 mL). IN NAOH (5 mL) was added. The mixture was stirred at rt for 2h. The solvent was evaporated. The residue was acidified with IN HCl, extracted with CH2Cl2 (3x), dried over MGSO4, filtered, and concentrated to dryness to give 4- (3-OXO-MORPHOLIN- 4-yl)-benzoic acid (0.41 g). LC/MS (ESI) 222.2 (M+H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4419 - 4427
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5987 - 5999
[3]Patent: WO2004/82687,2004,A1 .Location in patent: Page/Page column 107-108

2
[ 720720-60-5 ]
[ 764659-50-9 ]
(1R, 2S)-3-chloro-1H-indole-6-carboxylic acid {2-[4-(2-oxo-[1,3]oxazinan-3-yl)-benzoylamino]-cyclohexyl}-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4419 - 4427

3
[ 720720-60-5 ]
[ 766556-59-6 ]
(1R, 2S)-3-chloro-1H-indole-6-carboxylic acid {2-[4-(3-oxo-morpholin-4-yl)-benzoylamino]-cyclopentyl}-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4419 - 4427

4
[ 19614-15-4 ]
[ 720720-60-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4419 - 4427

5
[ 451-46-7 ]
[ 720720-60-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4419 - 4427

7
[ 720720-60-5 ]
[ 864296-33-3 ]
N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethyl]-4-(3-oxo-morpholin-4-yl)-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		254 mg (1.15 mmol) <strong>[720720-60-5]4-(morpholin-3-on-4-yl)-benzoic acid</strong> (prepared by synthesis sequence analogously to Example 30a, 2d and 21a) are placed in 5 ml DMF and 428 mg (1.0 mmol) PfTU and 514 mul (3.0 mmol) DIPEA are added. After stirring at ambient temperature for 10 minutes 232 mg (1.0 mmol) (1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamine-hydrochloride are added and the mixture is stirred for 16 hours at ambient temperature. Then the reaction mixture is filtered through basic aluminium oxide and evaporated down i. vac. The residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/methanol 100:0->90:10), the corresponding fractions are evaporated down i. vac., the residue is dissolved in acetonitrile/water and lyophilised. Yield: 77% C20H19ClN4O3 (398.85) Mass spectrum: (M+H)+=399/401 (chlorine isotope)

Reference： [1]Patent: WO2005/82895,2005,A1 .Location in patent: Page/Page column 11-112
[2]Patent: US2005/203078,2005,A1 .Location in patent: Page/Page column 41

8
[ 720720-60-5 ]
[ 721927-42-0 ]
N₁-(5-chloropyridin-2-yl)-N₂-((2S)-3-(dimethylamino)-3-oxo-2-[4-(3-oxomorpholin-4-yl)benzoyl]amino}propyl)ethanediamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 19h;	The compound (131 mg) obtained in Referential Example 10, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (125 mg), 1-hydroxybenzotriazole (64.8 mg) and triethylamine (0.0607 ml) were added to an N,N-dimethylformamide (5.0 ml) solution of the compound (250 mg) obtained in Referential Example 360. The resulting mixture was stirred at room temperature for 15 hours. The solvent was distilled off under reduced pressure. A saturated aqueous solution of sodium bicarbonate and methylene chloride were added to the residue to separate the layers. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography (methylene chloride:methanol = 30:1) on a silica gel column, whereby the title compound in the free form was obtained as a pale yellow foamy substance. The resulting product in the free form was dissolved in ethanol (2.0 ml) and methylene chloride (2.0 ml). A 1N hydrochloric acid ethanol solution (0.35 ml) was added to the resulting solution. After stirring at room temperature for 30 minutes, the reaction mixture was concentrated under reduced pressure. Diethyl ether was added to the residue. The solid thus precipitated was collected by filtration and washed, whereby the title compound (152 mg) was obtained.1H-NMR(DMSO-d6)delta: 2.85(3H,s), 2.94(3H,s), 3.09-3.56(4H,m), 3.14(3H,s), 3.57-3.66(1H, m), 3.72(1H, br s), 4.36-4.52(1H, m), 4.65-4.80(1H, m), 5.04-5.14(1H, m), 7.98(1H, d, J=8.8Hz), 8.13(1H, dd, J=8.8, 2.4Hz), 8.53(1H,d,J=2.4Hz), 8.64-8.73 (1H, m), 9.28 (1H, s) , 10.24(1H, s), 11.11-11.48(1H, m). MS (ESI)m/z: 538(M+H)+.

Reference： [1]Patent: EP1577302,2005,A1 .Location in patent: Page/Page column 249

9
[ 720720-60-5 ]
[ 1057651-04-3 ]
[ 1057647-23-0 ]

Yield	Reaction Conditions	Operation in experiment
39%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 72h;	Compounds 22 (113 mg, 0.510 mmol) and 36 (13550 mg, 0.506 mmol) were dissolved in DMF (5 mL). To the solution were added HOBt (68.4 mg, 0.506 mmol) and EDC·HCl (194 mg, 1.01 mmol). After stirring at room temperature for 3 d, the solvent was distilled off in vacuo. To the residue were added CH2Cl2 and saturated NaHCO3 aqueous solution. After extraction with CH2Cl2, combined organics were dried over Na2SO4 and concentrated in vacuo. EtOH was added to the residue, and the mixture was stirred at 50 C for 30 min. After cooling to room temperature, precipitate was collected by filtration. Obtained white powder was purified by column chromatography on silica gel (CH2Cl2/MeOH = 24:1) to obtain the title compound (92 mg, 0.195 mmol, 39%) as a white powder. MP: 243-24 C. IR (ATR) cm-1: 3286, 1651, 1622, 1603, 1556, 1520, 1504. 1H NMR (DMSO-d6) delta: 3.81 (2H, t, J = 5.0 Hz), 4.00 (2H, t, J = 4.9 Hz), 4.24 (2H, s), 4.45 (2H, d, J = 5.9 Hz), 7.20 (1H, dd, J = 4.2, 1.5 Hz), 7.24 (1H, t, J = 7.4 Hz), 7.28-7.36 (2H, m), 7.51 (1H, d, J = 7.8 Hz), 7.59 (2H, d, J = 7.6 Hz), 7.68 (1H, dd, J = 4.2, 1.2 Hz), 8.04 (2H, d, J = 7.6 Hz), 9.20 (1H, t, J = 5.6 Hz), 10.30 (1H, s). ESI-MS m/z: 470 (M+H)+. Anal. Calcd for C23H20ClN3O4S: C, 58.78; H, 4.29; N, 8.94; Cl, 7.54; S, 6.82. Found: C, 58.60; H, 4.33; N, 8.86; Cl, 7.36; S, 6.85.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 1623 - 1642

10
methyl 4-(3-oxo-4-morpholinyl)benzoate [ No CAS ]
[ 720720-60-5 ]

Yield	Reaction Conditions	Operation in experiment
93%		To the solution of compound 21 (1.21 g, 5.14 mmol) in CH2Cl2 (40 mL) were added dimethylsulfide (5.0 mL) and anhydrous aluminium chloride (2.06 g, 15.4 mmol). The mixture was stirred at room temperature for 8 h. After the solvent was distilled off in vacuo, to the obtained residue were added ice and dilute hydrochloric acid. The precipitate was collected by filtration to obtain the title compound (1.06 g, 4.79 mmol, 93%) as a white powder. 1H NMR (CDCl3) delta: 3.83 (2H, t, J = 5.1 Hz), 4.06 (2H, t, J = 5.1 Hz), 4.33 (2H, s), 7.46 (2H, d, J = 8.5 Hz), 8.08 (2H, d, J = 8.5 Hz), 12.35 (1H, br s). ESI-MS m/z: 222 (M+H)+.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 1623 - 1642

11
[ 23676-05-3 ]
[ 720720-60-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 1623 - 1642

12
[ 7470-38-4 ]
[ 720720-60-5 ]