[ CAS No. 67451-81-4 ] {[proInfo.proName]}

Name: 67451-81-4|3-(Morpholinomethyl)benzoic acid|97%
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SKU: A648964
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Quality Control of [ 67451-81-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 67451-81-4 ]

SDS Specification

Alternatived Products of [ 67451-81-4 ]

Product Details of [ 67451-81-4 ]

CAS No. :	67451-81-4	MDL No. :	MFCD05841588
Formula :	C₁₂H₁₅NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LZLRLAYVCUNAEX-UHFFFAOYSA-N
M.W :	221.25	Pubchem ID :	7152692
Synonyms :

Calculated chemistry of [ 67451-81-4 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	63.38
TPSA :	49.77 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) :	-9.2 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	-2.18
Log Po/w (WLOGP) :	0.68
Log Po/w (MLOGP) :	1.0
Log Po/w (SILICOS-IT) :	1.65
Consensus Log Po/w :	0.64

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.08
Solubility :	267.0 mg/ml ; 1.21 mol/l
Class :	Highly soluble
Log S (Ali) :	1.67
Solubility :	10200.0 mg/ml ; 46.3 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-2.37
Solubility :	0.946 mg/ml ; 0.00428 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.68

Safety of [ 67451-81-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 67451-81-4 ]

* 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.

Upstream synthesis route of [ 67451-81-4 ]
Downstream synthetic route of [ 67451-81-4 ]

[ 67451-81-4 ] Synthesis Path-Upstream 1~4

1
[ 190660-95-8 ]
[ 67451-81-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 50℃; for 16 h;	To a solution of methyl 3-(mo holinomethyl)benzoate (5.02 g, 21.0 mmol) in MeOH (100 mL) was added sodium hydroxide (21.0 mL, 42.0 mmol, 2 M). The mixture was heated at 50 °C for 16 h. The solvent was removed, residue was adjusted to pH=3 with 1M HC1, and the suspension was filtered. The solid was dissolved in ACN (15 mL) and concentrated to give 3-(morpholinomethyl)benzoic acid (4.6 g, 100percent) as a white solid used without further purification in the next step.

Reference： [1] Patent: WO2018/169777, 2018, A1, . Location in patent: Paragraph 0229

2
[ 110-91-8 ]
[ 1129-28-8 ]
[ 67451-81-4 ]

Yield	Reaction Conditions	Operation in experiment
41%	With sodium hydroxide In methanol; dichloromethane	EXAMPLE 14 3-Morpholin-4-yl-methyl-benzoic Acid Commercially available methyl 3-bromomethyl benzoate (5 g, 22 mmole) was dissolved in dichloromethane (20 mL) and morpholine (3.93 mL, 45 mmol) was added. The solution was allowed to stir for 12 h, and filtered. The solvent of the filtrate was removed under reduced pressure. The resulting crude ester was dissolved in methanol, and sodium hydroxide (4.6 mL of 5N solution) was added. The solution was stirred overnight at 40° C. for 12 h. The solvent was partially removed under reduced pressure. The crude was acidified, dichloromethane was added and the solution was cooled in ice. After one hour, it was filtered, to provide the title product (2.3 g, 41percent) as the white solid hydrochloride salt: ¹H-NMR (DMSO-d₆) δ13.1 (bs, 1H), 11.8 (bs, 1H), 8.14 (s, 1H), 7.92 (m, 2H), 7.65 (t, J=4 Hz, 1H), 4.39 (bs, 2H), 3.91(m, 4H), 3.12 (m, 4H). MS (EI-NEG):[M+]221; Anal.RP-HPLC: 99percent purity.

Reference： [1] Patent: US6355633, 2002, B1,

3
[ 99-36-5 ]
[ 67451-81-4 ]

Reference： [1] Patent: WO2018/169777, 2018, A1,

4
[ 1129-28-8 ]
[ 67451-81-4 ]

Reference： [1] Patent: WO2018/169777, 2018, A1,

[ 67451-81-4 ] Synthesis Path-Downstream 1~15

1
[ 67451-81-4 ]
[ 105535-46-4 ]
[ 913976-18-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2005,vol. 44,p. 2308 - 2313

2
[ 67451-81-4 ]
[ 123941-48-0 ]
7β-acetoxy-1α,9α-dihydroxy-8,13-epoxy-6β-[3-(4-morpholinomethyl)benzoyloxy]acetyloxy-labd-14-en-11-one hydrochloride [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2005,vol. 44,p. 2308 - 2313

3
[ 110-91-8 ]
[ 1129-28-8 ]
[ 67451-81-4 ]

Yield	Reaction Conditions	Operation in experiment
41%	With sodium hydroxide; In methanol; dichloromethane;	EXAMPLE 14 3-Morpholin-4-yl-methyl-benzoic Acid Commercially available methyl 3-bromomethyl benzoate (5 g, 22 mmole) was dissolved in dichloromethane (20 mL) and morpholine (3.93 mL, 45 mmol) was added. The solution was allowed to stir for 12 h, and filtered. The solvent of the filtrate was removed under reduced pressure. The resulting crude ester was dissolved in methanol, and sodium hydroxide (4.6 mL of 5N solution) was added. The solution was stirred overnight at 40 C. for 12 h. The solvent was partially removed under reduced pressure. The crude was acidified, dichloromethane was added and the solution was cooled in ice. After one hour, it was filtered, to provide the title product (2.3 g, 41%) as the white solid hydrochloride salt: 1H-NMR (DMSO-d6) delta13.1 (bs, 1H), 11.8 (bs, 1H), 8.14 (s, 1H), 7.92 (m, 2H), 7.65 (t, J=4 Hz, 1H), 4.39 (bs, 2H), 3.91(m, 4H), 3.12 (m, 4H). MS (EI-NEG):[M+]221; Anal.RP-HPLC: 99% purity.

Reference： [1]Patent: US6355633,2002,B1

4
[ 67451-81-4 ]
[ 28096-93-7 ]
(bis)sodium salt [ No CAS ]
[ 299181-00-3 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 33b 2,2'-[(E)-1,2-Ethenediyl]bis[5-[[3-(4-morpholinylmethyl)benzoyl]amino]benzenesulfonic Acid] The (bis)sodium salt was prepared from <strong>[67451-81-4]3-morpholin-4-yl-methyl-benzoic acid</strong>, Example 14 and commercially available 4,4'-diaminostilbene-2,2'-disulfonic acid (11%): ES-NEG [M-H]- 775.

Reference： [1]Patent: US6355633,2002,B1

5
[ 67451-81-4 ]
[ 934018-35-6 ]
7-(4-methoxyphenyl)-2-[3-(morpholin-4-ylmethyl)phenyl]-3H-imidazo[4,5-b]pyridine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	In trichlorophosphate; at 160.0℃; for 0.333333h;Microwave irradiation;	General Method DPOCl3 2 mL (solvent) was added to a mixture of the diamine Dl (1.0 equiv.), the carboxylic acid D2 (1.1 equiv.) and the reaction mixture was heated in a microwave reactor at +160 0C for 20 minutes. The product mixture was mixed with ice/water mixture. The products were collected by filtration, or by extraction with CH2Cl2. Purification by preparative HPLC, afforded each product as a base. The base was dissolved in CH2Cl2MeOH (9:1) and hydrochloric acid (IM HCl in diethyl ether) was added until precipitation formed. The solid hydrochloride salt was collected by filtration and dried.; Example 55; 7-(4-Methoxyphenyl)-2-[3-(morpholin-4-ylmethyl)phenyl]-3J?-imidazo[4,5-6]pyridine hydrochloride EPO <DP n="104"/>The title compound was prepared in accordance with the general method D using 4-(4- methoxyphenyl)pyridine-2,3-diamine (obtained from Example l(c)) (50 mg, 0.232 mmol) and 3-mophiholin-4-yhnethyl-benzoic acid (56 mg, 0.255 mmol), affording 0.041 g (45%) of the title compound.1H NMR (OMSO-d6) delta ppm; 11.21 (s, 1 H), 8.49 - 8.53 (m, 1 H), 8.44 (d, 1 H), 8.36 (d, 1 H), 8.29 (d, 2 H), 7.86 (d, 1 H), 7.70 (t, 1 H), 7.59 (d, 1 H), 7.17 (d, 3 H), 4.47 (s, 2 H), 3.92 - 4.01 (m, 2 H), 3.88 (s, 3 H), 3.79 (d, 2 H), 3.26 - 3.34 (m, 2 H), 3.09 - 3.21 (m, 2 H); MS (AP) m/z 401 (M+l).

Reference： [1]Patent: WO2007/40438,2007,A2 .Location in patent: Page/Page column 41; 102-103

6
[ 67451-81-4 ]
[ 649735-46-6 ]
[ 1016195-15-5 ]