[ CAS No. 1351413-50-7 ] {[proInfo.proName]}

Name: 1351413-50-7|(1-Methyl-2-oxo-1,2-dihydropyridin-4-yl)boronic acid|95%
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Quality Control of [ 1351413-50-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1351413-50-7 ]

Product Details of [ 1351413-50-7 ]

CAS No. :	1351413-50-7	MDL No. :	MFCD22418629
Formula :	C₆H₈BNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QIFVXSLMFCRLCB-UHFFFAOYSA-N
M.W :	152.94	Pubchem ID :	67814299
Synonyms :

Calculated chemistry of [ 1351413-50-7 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	41.79
TPSA :	62.46 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-8.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-1.16
Log Po/w (WLOGP) :	-1.93
Log Po/w (MLOGP) :	-1.14
Log Po/w (SILICOS-IT) :	-1.65
Consensus Log Po/w :	-1.18

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.4
Solubility :	61.6 mg/ml ; 0.403 mol/l
Class :	Very soluble
Log S (Ali) :	0.34
Solubility :	335.0 mg/ml ; 2.19 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.37
Solubility :	65.5 mg/ml ; 0.429 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.8

Safety of [ 1351413-50-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1351413-50-7 ]

* 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 [ 1351413-50-7 ]
Downstream synthetic route of [ 1351413-50-7 ]

[ 1351413-50-7 ] Synthesis Path-Upstream 1~2

1
[ 1160790-84-0 ]
[ 1351413-50-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With hydrogenchloride In 1,4-dioxane; water at 25℃; for 12 h;	(3) The residue from step (2) was dissolved in dioxane (500-1000 mL) and stirredConcentrated hydrochloric acid (500-1000 mL)25 ° C for 12 h,After the reaction was completed, extracted with ethyl acetate, the organic phase discarded,The aqueous product was evaporated to dryness under reduced pressure to give a clean product (53.3 g, 60percent yield).

Reference： [1] Patent: CN106986885, 2017, A, . Location in patent: Paragraph 0015; 0016; 0017

2
[ 214342-63-9 ]
[ 1351413-50-7 ]

Reference： [1] Patent: WO2011/149822, 2011, A1,

[ 1351413-50-7 ] Synthesis Path-Downstream 1~24

1
[ 214342-63-9 ]
[ 1351413-50-7 ]

Reference： [1]Patent: WO2011/149822,2011,A1

2
[ 1110641-70-7 ]
[ 1351413-50-7 ]
[ 1114561-85-1 ]

Yield	Reaction Conditions	Operation in experiment
88.2%		Example 2Synthesis of (S)-6-(2-hydroxy-2-methylpropyl)-3-((S)-l-(4-(l-methyl-2-oxo-l ,2- dihydropyridin-4-yl)phenyl)ethyl)-6-phenyl-l ,3-oxazinan-2-one monohydrate (2)Compound 2 is prepared using the procedure depicted in Scheme 4 and described below.Scheme 4A reaction flask is charged with (S)-3-((S)-l-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-l,3-oxazinan-2-one (19.66 g, 45.47 mmol) (see Ex. 588 of WO/2009/017664), compound 1 (7.65 g, 50.02 mmol), [1,1 '- bis(diphenylphosphino)ferroncene]dichloropalladium(II), complex with dichloromethane (37.40 mg, 0.046 mmol), potassium carbonate (18.85 g, 136.42 mmol) and 2-propanol (100 mL). The flask is evacuated and refilled with argon three times. The contents of the reactor are heated to 80C and held for about 6 hours at which time compound 1 is completely consumed. The contents of the reactor are then treated with a solution of N- acetyl-L-cysteine (0.75 g, 4.58 mmol) in 2-propanol (100 mL) and stirred at 80C for 2 hours. The resultant suspension is then filtered. (The suspension is maintained at 50C to 70C during the filtration step.) The resultant solids are then rinsed with 2-propanol (50 mL pre-heated to 70C). The combined filtrate and washes is heated to 70C, maintained at reduced pressure until about 150 ml of volatiles are removed, cooled to 65 C, and seeded with compound 2. The resultant suspension is stirred at 60 - 65C for 0.5 hours, cooled to 0C over about 2 hours, and maintained at 0C for 1 hour. The resultant solids are collected by filtration and washed with cold 2-propanol (50 mL). The solids are then recrystallized from a mixture of 2-propanol (40 mL) and water (200 mL) to provide compound 2 (monohydrate) as a white solid. Yield: 19.38 g, 88.2 % yield based on BI135541. Purity: 98.96 wt . Analysis of the product agrees with the data reported in Example 48, Method 2 of WO/2009/134400 which describes the synthesis of the monohydrate of compound 1 by reacting 4-iodo-l-methylpyridin-2(lH)-one with (S)-6-(2- hydroxy-2-methylpropyl)-6-phenyl-3-((S)-l-(4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2- yl)phenyl)ethyl)- 1 ,3-oxazinan-2-one.

Reference： [1]Patent: WO2011/149822,2011,A1 .Location in patent: Page/Page column 11-12
[2]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3649 - 3657

3
C₈H₁₂BNO₃ [ No CAS ]
[ 1351413-50-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With hydrogenchloride; water; In tetrahydrofuran; at 5 - 20℃; for 6h;	Example 1Synthesis of l-methyl-2-oxo-l,2-dihydropyridin-4-ylboronic acid (1). Compound 1 is prepared using the procedure depicted in Scheme 3 and described below. Scheme 31Step 1. A solution of isopropylmagnesium chloride (175 mL, 1.85 M in THF, 0.32 mol, 1.54 eq.) is charged to a 500-mL jacketed reactor under nitrogen atmosphere with mechanical agitation. The contents of the reactor are cooled to -18C and treated with a solution of 4-bromo-l-methylpyridine-2(lH)-one (40.0 g, 0.21 mol, 1.00 eq.) over about 1 hour. The rate of addition is controlled to maintain a reaction temperature of no higher than -15C. The contents of the reactor are warmed to -10C, mixed for 1 hour, and warmed to 20C.Step 2. The contents of the reactor from Step 1 are cooled to -20C and treated with neat trimethylborate (38 mL, 0.36 mol, 1.62 eq.) at a rate sufficiently slow(approximately 1 hour) to keep the batch temperature at or below -15C. The contents of the reactor are then warmed to -10C, mixed for 1 hour, and warmed to 20C.Step 3. Hydrochloric acid (140 mL, 2.56 N, 0.36 mol, 1.70 eq.) is cooled to about5C and treated with the reaction mixture from Step 2. The rate of addition is slow enough to maintain a reaction temperature of less than 25C. The contents of the reactor are then mixed at 20C for 6 hours. The resultant solids are collected by filtration, washed with isopropyl acetate (50 mL), and dried under reduced pressure at 21C to provide a first crop of 1 as a white crystalline solid. Yield: 14.72 g, 42%. Purity: 98.9 A% by HPLC (220 nm); 91.7 wt% by H NMR.H NMR (DMSO-d6, 500 MHz) delta 8.37 (brs, 2H), 7.59 (d, / = 6.60 Hz, 1H), 6.78 (s, 1H), 6.40 (d, / = 6.55 Hz, 1H), 3.40 (s, 3H).MS (ES) m/z = 154 [M+H]+.A second batch of product is collected by reducing the volume of the filtrate under reduced pressure, adding isopropyl acetate (200 mL) at 21C to the concentrated solution, and mixing the resultant slurry for 2 hours. The resultant solids are collected by filtration, washed with isopropyl acetate (50 mL) and dried under reduced pressure at 21C to provide a second crop of 1 as a white solid. Yield: 10.42 g, 28%. Purity: 98.0 A% by HPLC (220 nm); 85.6 wt% by *H NMR.Total yield based on both crops of 1: 70%.

Reference： [1]Patent: WO2011/149822,2011,A1 .Location in patent: Page/Page column 9-10

4
[ 1198319-60-6 ]
[ 1351413-50-7 ]
[ 1470082-25-7 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 8834 - 8848

5
[ 1351413-50-7 ]
(4S)-7-chloro-N-(pyridin-3-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide [ No CAS ]
(9S)-5-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-N-(pyridin-3-yl)-1,6,8-triazatricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-8-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30.2%	With potassium phosphate; palladium diacetate; XPhos; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere;	To a degassed solution of (4S)-7-chloro-N-(pyridin-3-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide (400 mg, 1.267 mmol), potassium phosphate (537 mg, 2.53 mmol) and <strong>[1351413-50-7](1-methyl-2-oxo-1,2-dihydropyridin-4-yl)boronic acid</strong> (291 mg, 1.900 mmol) in mixture of 1,4-dioxane (9 mL) and water (1 mL) were added X-Phos (60.4 mg, 0.127 mmol) and Pd(OAc)2 (14.22 mg, 0.063 mmol) at RT and heated at 100 C. for 16 h. Allowed the reaction mixture to RT, organic solvent was removed by rotary evaporation and diluted with water (50 mL), extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated to obtain the crude product. The crude product was purified by flash column chromatography (silica-gel: 100-200 mesh, eluent: 03% MeOH in DCM) to afford (4S)-7-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-N-(pyridin-3-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide (150 mg, 0.383 mmol, 30.2% yield) as an off white solid (TLC: Rf 0.4, 10% MeOH/DCM), LCMS (m/z): 389.22 [M+H]+. 1H NMR (400 MHz, CDCl3): delta ppm 12.92 (s, 1H), 8.57 (d, J=2.63 Hz, 1H), 8.06-8.32 (m, 2H), 7.62 (d, J=7.89 Hz, 1H), 7.48 (d, J=7.02 Hz, 1H), 7.25-7.32 (m, 2H), 6.95 (d, J=1.75 Hz, 1H), 6.63 (dd, J=7.02, 1.97 Hz, 1H), 5.68 (dd, J=5.92, 3.29 Hz, 1H), 3.62 (s, 3H), 3.19-3.39 (m, 2H), 3.15 (d, J=12.06 Hz, 1H), 2.84-3.09 (m, 1H), 2.19-2.39 (m, 1H), 2.05-2.19 (m, 1H).
30.2%	With potassium phosphate; palladium diacetate; XPhos; In 1,4-dioxane; water; at 100℃; for 16h;	To a degassed solution of (4,S)-7-chloro-N-(pyridin-3-yl)-3,4-dihydro-l,4- methanopyrido[2,3-£][l,4]diazepine-5(2H)-carboxamide (400 mg, 1.267 mmol), potassium phosphate (537 mg, 2.53 mmol) and (l-methyl-2-oxo-l,2-dihydropyridin-4- yl)boronic acid (291 mg, 1.900 mmol) in mixture of 1,4-dioxane (9 mL) and water (1 mL) were added X-Phos (60.4 mg, 0.127 mmol) and Pd(OAc)2 (14.22 mg, 0.063 mmol) at RT and heated at 100 C for 16h. Allowed the reaction mixture to RT, organic solvent was removed by rotary evaporation and diluted with water (50 mL), extracted with ethyl acetate (3x50 mL). The combined organic layer was washed with brine (50 mL), dried over anhydrous Na2S04 and concentrated to obtain the crude product. The crude product was purified by flash column chromatography (silica-gel: 100-200 mesh, eluent: 03% MeOH in DCM) to afford (45)-7-(l-methyl-2-oxo-l,2-dihydropyridin-4-yl)-N-(pyridin-3- yl)-3,4-dihydro-l,4-methanopyrido[2,3-^][l,4]diazepine-5(2H)-carboxamide (150 mg, 0.383 mmol, 30.2 % yield) as an off white solid (TLC: Rf 0.4, 10% MeOH/DCM), LCMS (/// r): 389.22 [M+H]+.1H NMR (400 MHz,CDCl3): delta ppml2.92 (s, 1 H), 8.57 (d, J=2.63 Hz, 1 H), , 8.06 - 8.32 (m, 2 H), 7.62 (d, J=7.89 Hz, 1 H), 7.48 (d, J=7.02 Hz, 1 H), 7.25 - 7.32 (m, 2 H), 6.95 (d, J=1.75 Hz, 1 H), 6.63 (dd, J=7.02, 1.97 Hz, 1 H), 5.68 (dd, J=5.92, 3.29 Hz, 1 H), 3.62 (s, 3H), 3.19-3.39 (m, 2 H), 3.15 ( d, J=12.06 Hz, 1 H), 2.84 - 3.09 (m, 1 H), 2.19-2.39 (m, 1 H), 2.05-2.19 (m, 1 H).

Reference： [1]Patent: US2015/152108,2015,A1 .Location in patent: Paragraph 1447; 1448; 1449
[2]Patent: WO2016/79709,2016,A1 .Location in patent: Page/Page column 517-518

6
[ 1351413-50-7 ]
(4S)-7-chloro-N-(pyrazin-2-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide [ No CAS ]
(9S)-5-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-N-(pyrazin-2-yl)-1,6,8-triazatricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-8-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.5%	With potassium phosphate; palladium diacetate; XPhos; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere;	Potassium phosphate (939 mg, 4.43 mmol) and <strong>[1351413-50-7](1-methyl-2-oxo-1,2-dihydropyridin-4-yl)boronic acid</strong> (462 mg, 3.322 mmol) were added to a solution of (4S)-7-chloro-N-(pyrazin-2-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide (700 mg, 2.215 mmol) in mixture of 1,4-dioxane: water (10 mL, 8:2) at RT. This mixture was purged with argon for 30 min. PdOAc2 (49.62 mg, 0.221 mmol) and X-Phos (211.2 mg, 0.443 mmol) were added to the reaction mixture and then stirred at 100 C. for 16 h. The reaction mixture was cooled to room temperature, concentrated in vacuo, residue was partitioned between water (40 mL) and EtOAc (80 mL). Organic layer was separated and dried over anhydrous Na2SO4, filtered and filtrate was evaporated to obtain crude compound. The crude compound was purified by column chromatography using silica gel (100-200 mesh) 3% methanol in dichloromethane as a eluent to afford (4S)-7-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)-N-(pyrazin-2-yl)-3,4-dihydro-1,4-methanopyrido[2,3-b][1,4]diazepine-5(2H)-carboxamide (110 mg, 0.270 mmol, 28.5% yield) as a pale yellow solid. (TLC eluent: 10% MeOH in DCM Rf: 0.4; UV active), LCMS (m/z): 390.30 [M+H]+. 1H NMR (400 MHz, CDCl3): delta ppm 13.53 (s, 1H), 9.53 (s, 1H), 8.34-8.28 (m, 2H), 7.63 (d, J=8.11 Hz, 1H), 7.43 (t, J=7.78 Hz, 2H), 7.20 (d, J=1.75 Hz, 1H), 7.04 (dd, J=7.23, 1.97 Hz, 1H), 5.70 (dd, J=5.92, 3.07 Hz, 1H), 3.62 (s, 3H), 3.33-3.14 (m, 3H), 3.03 (dd, J=12.06, 3.29 Hz, 1H), 2.40-2.30 (m, 1H), 2.09 (dt, J=13.92, 6.85 Hz, 1H)
28.5%	With potassium phosphate; palladium diacetate; XPhos; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere;	Potassium phosphate (939 mg, 4.43 mmol) and (l-methyl-2-oxo-l,2-dihydropyridin-4- yl)boronic acid (462 mg, 3.322 mmol) were added to a solution of (4,S)-7-chloro-N- (pyrazin-2-yl)-3,4-dihydro-l,4-methanopyrido[2,3-^][l,4]diazepine-5(2H)-carboxamide (700 mg, 2.215mmol) in mixture of l,4-dioxane:water(10 mL, 8:2) at RT. This mixture was purged with argon for 30 min. PdOAc2 (49.62 mg, 0.221 mmol) and X-Phos (211.2 mg, 0.443mmol) were added to the reaction mixture and then stirred at 100 C for 16h. The reaction mixture was cooled to room temperature, concentrated in vacuo, residue was partitioned between water (40 mL) and EtOAc (80 mL). Organic layer was separated and dried over anhydrous Na2S04, filtered and filtrate was evaporated to obtain crude compound. The crude compound was purified by column chromatography using silica gel (100-200 mesh) 3% methanol in dichloromethane as a eluent to afford(4,S)-7-(l-methyl-2- oxo-l,2-dihydropyridin-4-yl)-N-(pyrazin-2-yl)-3,4-dihydro-l,4-methanopyrido[2,3- 6][l,4]diazepine-5(2H)-carboxamide (110 mg, 0.270 mmol, 28.5 % yield) as a pale yellow solid.(TLC eluent: 10% MeOH in DCM Rf: 0.4; UV active), LCMS (m/z): 390.30 [M+H]+.1H NMR (400 MHz, CDC13): delta ppm 13.53 (s, 1 H), 9.53 (s, 1 H), 8.34-8.28 (m, 2 H), 7.63 (d, J=8.11 Hz, 1 H), 7.43 (t, J=7.78 Hz, 2 H), 7.20 (d, J=1.75 Hz, 1 H), 7.04 (dd, J=7.23, 1.97 Hz, 1 H), 5.70 (dd, J=5.92, 3.07 Hz, 1 H), 3.62 (s, 3 H),3.33-3.14 (m, 3 H), 3.03 (dd, J=12.06, 3.29 Hz, 1 H), 2.40-2.30 (m, 1 H), 2.09 (dt, J=13.92, 6.85 Hz, 1 H)

Reference： [1]Patent: US2015/152108,2015,A1 .Location in patent: Paragraph 1558; 1559; 1560
[2]Patent: WO2016/79709,2016,A1 .Location in patent: Page/Page column 547

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[ 15864-32-1 ]
[ 1351413-50-7 ]
[ 1608501-53-6 ]