[ CAS No. 833472-82-5 ] {[proInfo.proName]}

Name: 833472-82-5|(3-(3-Methoxy-3-oxopropyl)phenyl)boronic acid|98%
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SKU: A652817
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Quality Control of [ 833472-82-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 833472-82-5 ]

SDS Specification

Alternatived Products of [ 833472-82-5 ]

Product Details of [ 833472-82-5 ]

CAS No. :	833472-82-5	MDL No. :	MFCD04115648
Formula :	C₁₀H₁₃BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IPXZIWCEVNDHFD-UHFFFAOYSA-N
M.W :	208.02	Pubchem ID :	4993880
Synonyms :

Calculated chemistry of [ 833472-82-5 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	56.94
TPSA :	66.76 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) :	-6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.91
Log Po/w (WLOGP) :	-0.53
Log Po/w (MLOGP) :	0.55
Log Po/w (SILICOS-IT) :	-0.16
Consensus Log Po/w :	0.16

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.67
Solubility :	4.46 mg/ml ; 0.0214 mol/l
Class :	Very soluble
Log S (Ali) :	-1.9
Solubility :	2.63 mg/ml ; 0.0127 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.18
Solubility :	1.37 mg/ml ; 0.00659 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.75

Safety of [ 833472-82-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 833472-82-5 ]

* 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 [ 833472-82-5 ]

[ 833472-82-5 ] Synthesis Path-Downstream 1~24

1
[ 833472-82-5 ]
[ 833472-81-4 ]
3-(3-{2-morpholin-4-yl-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidin-4-yl}-phenyl)-propionic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-(2-methoxycarbonylethyl)phenylboronic acid,; 4-{4-chloro-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyrimidin-2-yl}-morpholine With potassium phosphate In 1,4-dioxane for 0.166667h; Stage #2: In 1,4-dioxane at 80℃; for 16.08h;	1.M.1 M. 3- (3- {2-MORPHOLIN-4-YL-6-F 4- (3-TRIFLUOROMETHYL-PYRIDIN-2-YL)-PIPERAZIN-1-YLL-PYRIMIDIN- 4-YL}-PHENYL)-PROPIONIC acid; 1. 3-(3-{2-Morpholin-4-yl-6-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]- pyrimidin-4-yl}-phenyl)-propionic acid methyl ester Purge a solution of 4- {4-chloro-6- [4- (3-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]- PYRIMIDIN-2-YL}-MORPHOLINE (142 mg, 0. 33 mmol), (3- (2- methoxycarbonylethyl) phenyl) boronic acid (COMBI-BLOCKS, Inc., San Diego, CA ; 104 mg, 0. 5 mmol) and K3PO4 (2M, 3311lL) in dioxane with nitrogen for 10 minutes. Add Pd (PPh3) 4 (19 mg, 0. 017 mmol) and purge for an additional 5 minutes. Seal the contents in a reaction vial and heat at 80°C for 16 hours. Partition the mixture between EtOAc and water, dry (NA2S04) the organic layer and concentrate under reduced pressure. Filter the residue through a small pad of silica gel eluting with 50% ETOAC/HEXANES. Concentrate under reduced pressure to give the title compound.

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - WO2005/7648, 2005, A2 Location in patent: Page 81-82

2
[ 833472-82-5 ]
[ 1186615-58-6 ]
N-(N-tert-butoxycarbonylpiperidin-4-ylmethyl), N-({2-[(4-cyanophenyl)-(3-methyl-3H-imidazol-4-ylmethyl)-amino]-ethyl})(3'-(2-methoxycarbonylethyl)-biphenyl)-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	In N,N-dimethyl-formamide at 110℃; for 16h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Hast, Michael A.; Fletcher, Steven; Cummings, Christopher G.; Pusateri, Erin E.; Blaskovich, Michelle A.; Rivas, Kasey; Gelb, Michael H.; Van Voorhis, Wesley C.; Sebti, Said M.; Hamilton, Andrew D.; Beese, Lorena S. [Chemistry and Biology, 2009, vol. 16, # 2, p. 181 - 192]

3
[ 151583-29-8 ]
[ 201733-56-4 ]
[ 833472-82-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; dimethyl sulfoxide; at 90℃;Inert atmosphere; Sealed tube;	Example 37B: 3-(3-methoxy-3-oxopropyl)phenylboronic acid j00413j DMSO (6.86 mL) and dioxane (6.86 mL) were degassed for 15 mm bybubbling with argon. Meanwhile, Example 37A (400 mg, 1.645 mmol), KOAc (404 mg,4.11 mmol), and bis(neopentyl glycolato)diboron (520 mg, 2.304 mmol) were placed in amicrowave tube. To these compounds was added the degassed solvents. The tube was sealed and degassed for an additional 15 mi [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (135 mg, 0.165 mmol) was subsequently added, the tubesealed, and heated to 90 C and allowed to stir overnight. The reaction was diluted withEtOAc and washed twice with brine, dried (Na2SO4), filtered, and concentrated in vacuo.The crude reaction mixture was purified by Prep LC (Axia Luna 5 t Cl 8 3 Ox 100 mmcolumn, 10 mm gradient from 40 to 100% B in A, A = 10:90:0.1 MeCN:H20:TFA, B =90:10:0.1 MeCN:H20:TFA) to yield Example 37B (O.224g, 64%) which was usedimmediately after purification.

Reference： [1]Patent: WO2014/201073,2014,A1 .Location in patent: Paragraph 00413

4
[ 833472-82-5 ]
4-(difluoromethoxy)-3-fluoro-5-((methylamino)methyl)aniline dihydrochloride [ No CAS ]
[ 298-12-4 ]
[ 873-74-5 ]
methyl 3-(3-(2-((5-amino-2-(difluoromethoxy)-3-fluorobenzyl)(methyl)amino)-1-(4-cyanophenylamino)-2-oxoethyl)phenyl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 3-(2-methoxycarbonylethyl)phenylboronic acid,; Glyoxilic acid; 4-Aminobenzonitrile In N,N-dimethyl-formamide; acetonitrile at 80℃; for 3h; Stage #2: 4-(difluoromethoxy)-3-fluoro-5-((methylamino)methyl)aniline dihydrochloride With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile	37.37C Example 3 7C: Methyl 3 -(3 -(2-((5-amino-2-(difluoromethoxy)-3fluorobenzyl)(methyl)amino)- 1 -(4-cyanophenylamino)-2-oxoethyl)phenyl)propanoate Example 3 7C: Methyl 3 -(3 -(2-((5-amino-2-(difluoromethoxy)-3fluorobenzyl)(methyl)amino)- 1 -(4-cyanophenylamino)-2-oxoethyl)phenyl)propanoate j00414j Example 37B (224 mg, 1.077 mmol), p-aminobenzonitrile (127 mg, 1.077 mmol), and glyoxylic acid monohydrate (99 mg, 1.077 mmol) were dissolved in DMF (2.99 mL) and MeCN (8.97 mL) and heated to 80 °C and stirred for 3 h. The reaction was cooled to ambient temperature. Intermediate 7 (379 mg, 1.292 mmol), DIPEA (940 .iL, 5.38 mmol), and BOP (476 mg, 1.077 mmol) were added and allowed to stirovernight. The reaction was diluted with water and extracted thrice with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was purified by silica gel column chromatography (0 to 100% EtOAc in hexanes) to yield Example 37C (0.347 g, 60%). MS (ESI) m/z: 541.2 (M+H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2014/201073, 2014, A1 Location in patent: Paragraph 00414

5
[ 42287-90-1 ]
[ 833472-82-5 ]