[ CAS No. 1386874-06-1 ] {[proInfo.proName]}

Name: 1386874-06-1|(S)-8-(5-(2-Hydroxypropan-2-yl)pyridin-3-yl)-1-(2-methoxypropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one|98%
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Quality Control of [ 1386874-06-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1386874-06-1 ]

SDS Specification

Alternatived Products of [ 1386874-06-1 ]

Product Details of [ 1386874-06-1 ]

CAS No. :	1386874-06-1	MDL No. :	MFCD28411368
Formula :	C₂₃H₂₆N₄O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ACCFLVVUVBJNGT-AWEZNQCLSA-N
M.W :	406.48	Pubchem ID :	57519748
Synonyms :	LY3023414;GTPL8918	Chemical Name :	(S)-8-(5-(2-Hydroxypropan-2-yl)pyridin-3-yl)-1-(2-methoxypropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one

Calculated chemistry of [ 1386874-06-1 ]

Physicochemical Properties

Num. heavy atoms :	30
Num. arom. heavy atoms :	19
Fraction Csp3 :	0.35
Num. rotatable bonds :	5
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	118.38
TPSA :	82.17 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-7.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.15
Log Po/w (XLOGP3) :	1.74
Log Po/w (WLOGP) :	3.1
Log Po/w (MLOGP) :	1.56
Log Po/w (SILICOS-IT) :	3.33
Consensus Log Po/w :	2.57

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.6
Solubility :	0.103 mg/ml ; 0.000254 mol/l
Class :	Soluble
Log S (Ali) :	-3.08
Solubility :	0.336 mg/ml ; 0.000827 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-6.13
Solubility :	0.000298 mg/ml ; 0.000000733 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.84

Safety of [ 1386874-06-1 ]

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

Application In Synthesis of [ 1386874-06-1 ]

* 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 [ 1386874-06-1 ]

[ 1386874-06-1 ] Synthesis Path-Downstream 1~17

1
[ 97-67-6 ]
[ 1386874-06-1 ]
[ 1386874-17-4 ]

Yield	Reaction Conditions	Operation in experiment
	In acetone;	Example 4 can be prepared by suspending free base (53.5 mg) in acetone (2 mL) and then incorporating L-malic acid (22 mg). Solids dissolve into a clear solution. The white crystalline solids precipitate from the solution. Vacuum filter and air dry the solids. Dry the malate salt in vacuum oven (65 C.) overnight to provide the title compound. The conditions to obtain the X-Ray powder diffraction (XRD) of Example 4 are essentially the same as the conditions described in Example 2. Thus, a prepared sample of the title compound is characterized by an XRD pattern using CuKa radiation as having diffraction peaks (2-theta values) as described in Table 4 below. Specifically the pattern contains a peak at 5.39 in combination with one or more of the peaks selected from the group consisting of 10.33, 12.16, 15.57 and 20.08 with a tolerance for the diffraction angles of 0.2 degrees

Reference： [1]Patent: US2012/184577,2012,A1 .Location in patent: Page/Page column 8

2
[ 1386874-21-0 ]
[ 75-16-1 ]
[ 1386874-06-1 ]

Yield	Reaction Conditions	Operation in experiment
75.8%		To a solution of ethyl 5-[1-[(2S)-2-methoxypropyl]-3-methyl-2-oxo-imidazo[4,5-c]quinolin-8-yl]pyridine-3-carboxylate (32.0 g, 76.1 mmol) in tetrahydrofuran (320 mL), slowly add MeMgBr (1.4M in tetrahydrofuran/toluene, 221.4 g, 6.92*) solution under N2 protection with temperature below 0 C. Stir the mixture at -5~0 C. for one hour under N2 protection. Add NH4Cl solution (15%, 320 mL) slowly to quench the reaction while keeping the temperature below 25 C. Then add ethyl acetate (320 mL). Warm up the mixture to 25~30 C. and stir for half hour. After separation of two layers, back extract the aqueous layer with tetrahydrofuran (160 mL). Wash the combined organic with brine (192 mL). Add active charcoal (1.6 g) to the organic layer and stir at 65~75 C. for 4-5 hours. Filter the mixture with Kieselguhr Silica-Thiol (1.6 g). Stir the organic layer at 65~75 C. for 2-3 hours; the mixture is then filtered by Kieselguhr Silica-Thiol. The organic layer is removed under vacuum and the re-crystallized with ethyl acetate/tetrahydrofuran to give 8-[5-(1-hydroxy-1-methylethyl)pyridin-3-yl]-1-[(2S)-2-methoxypropyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one as a light yellow solid (22.34 g, 72.2%). To a three-necked flask add 8-[5-(1-hydroxy-1-methylethyl)pyridin-3-yl]-1-[(2S)-2-methoxypropyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one prepared as above in this Method 3 (50.0 g, 123 mmol) and tetrahydrofuran (1500 mL). Stir the mixture and heat it to 45-55 C. to form an absolute solution. Filter and concentrate the filtrate under vacuum below 45 C. to 2.0-3.0V and add ethyl acetate (500 mL), then concentrate under vacuum below 45 C. to 7~8V. Stir the slurry at 70~80 C. for 6-10 hours, then cool to 20~25 C. and filter. Add ethyl acetate (135-140 g) and ethanol (13.5-14.0 g) to the residue. Stir the slurry at 70~80 C. for 6-10 hours; then cool to 20~25 C. and filter. Concentrate under vacuum to give the title compound as pale yellow solid (37.9 g, 75.8%). 1H NMR (CDCl3, 400 MHz) delta 8.86 (d, 1H, J=2 Hz), 8.76 (d, 1H, J=2.4 Hz), 8.71 (s, 1H), 8.64 (d, 1H, J=1.6 Hz), 8.21 (t, 2H), 7.85 (d, 1H, J=6.8 Hz), 4.36 (q, 2H), 3.88 (m, 1H), 3.62 (s, 3H), 3.23 (s, 3H), 2.79 (s, 1H), 1.95 (s, 1H), 1.71 (d, 6H, J=0.8 Hz), 1.33 (d, 3H, J=6.4 Hz)

Reference： [1]Patent: US2012/184577,2012,A1 .Location in patent: Page/Page column 5; 6

3
[ 20986-40-7 ]
[ 1386874-06-1 ]

Reference： [1]Patent: US2012/184577,2012,A1
[2]Patent: US2012/184577,2012,A1
[3]Patent: US2012/184577,2012,A1

4
[ 1386874-06-1 ]
[ 110-17-8 ]
[ 1386874-19-6 ]

Yield	Reaction Conditions	Operation in experiment
	In n-heptane; butan-1-ol; at 90℃;	Example 5 can be prepared as by adding free base <strong>[1386874-06-1]8-[5-(1-hydroxy-1-methylethyl)pyridin-3-yl]-1-[(2S)-2-methoxypropyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one</strong> (60.2 mg) to 1-butanol (0.5 mL) and then add 21.9 mg fumaric acid. Add heptane (50.5 mL), which produces thick white slurry, and stir at 90 C./500 rpm. Vacuum filter and dry under nitrogen. Solids are lost during recovery from filtration, though sufficient for XRD. Additional crystalline fumarate salt is prepared by adding free base (101.0 mg) to 1-butanol (0.5 mL) and then add 34 mg fumaric acid. Add heptane (60.5 mL) and crystalline seeds of the fumarate salt from first preparation and stir the mixture at 90 C./500 rpm for 1 hour. Recover the solids by vacuum filtration and dry the solids under nitrogen. Further dry the solids in a vacuum oven (65 C.) overnight to provide the title compound. The conditions to obtain the X-Ray powder diffraction (XRD) of Example 5 are essentially the same as the conditions described in Example 2

Reference： [1]Patent: US2012/184577,2012,A1 .Location in patent: Page/Page column 8

5
[ 29681-44-5 ]
[ 1386874-06-1 ]

Reference： [1]Patent: US2012/184577,2012,A1
[2]Patent: US2012/184577,2012,A1

6
[ 40472-88-6 ]
[ 1386874-06-1 ]

Reference： [1]Patent: US2012/184577,2012,A1

7
[ 40472-88-6 ]
[ 1386874-33-4 ]
[ 1386874-06-1 ]

Yield	Reaction Conditions	Operation in experiment
51%		Purge nitrogen through a suspension of 2-(5-bromo-3-pyridyl)propan-2-ol (100 g, 464 mmol, 1.25 eq.), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (141.4 g, 557 mmol, 1.5 eq.), and potassium acetate (127.5 g, 1.3 mol) in 1,4-dioxane (2.6 L) for 30 minutes at room temperature. Add dichloro-((bis-diphenylphosphino)ferrocenyl)-palladium(II) dichloromethane adduct (9 g, 11.14 mmol) under nitrogen and heat the mixture to 90 C. Stir the mixture for 3 hours. Cool the reaction mixture to 80 C. and then add 8-bromo-1-[(2S)-2-methoxypropyl]-3-methyl-imidazo[4,5-c]quinolin-2-one (130 g, 371 mmol), a solution of sodium carbonate (118 g, 1.1 mol) in water (910 mL), and dichloro-((bis-diphenylphosphino)ferrocenyl)-palladium(II) dichloromethane adduct (9 g, 11.14 mmol). Stir the mixture for 1.5 hours at the same temperature. Allow phase separation to obtain the organic layer and cool it to 40 C. before concentration in vacuo. Purify the residue (350 g) by silica gel column chromatography with an eluting solvent mixture gradient of dichloromethan/ethyl acetate/methanol from 1:1:1 to 1:1:20. Obtain product-containing fractions. Concentrate and slurry the residue in ethyl acetate (10 L/kg) at 40 C. for 15 minutes, filter and wash the solid with ethyl acetate (2×1 L/kg) and methyl tert-butyl ether (2×2 L/kg). Dissolve the washed solid in methanol (10 L/kg), treat with SiliaBond Thiol (0.4 g/g) to remove residual metal. Stir the suspension at 23 C. for 4 h, and filter. Wash the solid with methanol (1 L/kg). Combine all filtrate and methanol washes and concentrate in vacuo. Retain the solid in solvent (about 100 mL). Material crystallizes from the solvent. Filter solid material and dry at 1 mbar/40 C. overnight to afford the titled compound as a white solid (77 g, 51%). MS (ESI) m/z (M+H)+407.1. 1H NMR (500.23 MHz, DMSO): 9.05 (s, 1H), 8.95 (d, J=2.2 Hz, 1H), 8.79 (d, J=2.0 Hz, 1H), 8.69 (d, J=1.5 Hz, 1H), 8.33 (t, J=2.1 Hz, 1H), 8.18 (d, J=8.8 Hz, 1H), 8.12 (dd, J=1.7, 8.8 Hz, 1H), 5.41 (s, 1H), 4.56 (dd, J=8.3, 15.2 Hz, 1H), 4.37 (dd, J=4.2, 15.2 Hz, 1H), 3.85-3.80 (m, 1H), 3.57 (s, 3H), 3.12 (s, 3H), 1.56 (d, J=1.2 Hz, 6H), 1.26 (d, J=6.1 Hz, 3H)

Reference： [1]Patent: US2012/184577,2012,A1 .Location in patent: Page/Page column 5; 6

8
[ 122794-99-4 ]
[ 1386874-06-1 ]

Reference： [1]Patent: US2012/184577,2012,A1
[2]Patent: US2012/184577,2012,A1
[3]Patent: US2012/184577,2012,A1
[4]Patent: US2012/184577,2012,A1
[5]Patent: US2012/184577,2012,A1
[6]Patent: US2012/184577,2012,A1

9
[ 101937-44-4 ]
[ 1386874-06-1 ]

10
[ 206257-39-8 ]
[ 1386874-06-1 ]

11
[ 916326-10-8 ]
[ 1386874-06-1 ]

Reference： [1]Patent: US2012/184577,2012,A1

12
[ 1257431-63-2 ]
[ 1386874-33-4 ]
[ 1386874-06-1 ]

Yield	Reaction Conditions	Operation in experiment
44%	With potassium fluoride;tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; water; at 65 - 70℃;Inert atmosphere; Sealed tube;	Dissolve 8-bromo-1-[(2S)-2-methoxypropyl]-3-methyl-imidazo[4,5-c]quinolin-2-one (0.600 g, 1.7 mmol) and 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridyl]propan-2-ol (0.9 g, 3.43 mmole) in tetrahydrofuran (75 mL) and water (7.5 mL) in a sealed tube. Purge the mixture with nitrogen. Add potassium fluoride (400 mg, 6.89 mmole), tris(dibenzylideneacetone)dipalladium (0) (200 mg, 0.22 mmole) and tri-tert-butylphosphonium tetrafluoroborate (200 mg, 0.68 mmole). Seal the reaction in nitrogen and heat at 65-70 C. overnight. Cool the mixture to room temperature, filter to remove inorganic residue. Concentrate the filtrate and dilute it with dichloromethane (120 mL) and water (30 mL). Separate the organic layer and dry it over magnesium sulfate powder. Concentrate it in vacuo to brown oil. Purify the residue by silica gel column chromatography with eluting solvent of 30-65% ethyl acetate in hexane, then with 0-7% methanol in dichloromethane. Concentrate fractions containing the product and co-evaporate with diethyl ether (2×10 mL), acetone (10 mL), acetone and diethyl ether (10 mL each) subsequently. Dry the solid residue to afford the titled compound as an orange powder (0.30 g, 44%). MS (ESI) m/z (M+H)+407.0

Reference： [1]Patent: US2012/184577,2012,A1 .Location in patent: Page/Page column 5; 6

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate;Purification / work up;	The impure free base (Example 1) is slurried in ethylacetate, with a white solid starting to precipitate from a brownish solution. The solid is filtered in a glove box placed inside the ventilation hood and is allowed to dry in the vacuum inside the glove box overnight. The product is left under vacuum overnight (11 g, 63.18% yield)

14
[ 1386874-30-1 ]
[ 1386874-06-1 ]

15
[ 1386874-27-6 ]
[ 1386874-06-1 ]

16
[ 1369532-69-3 ]
[ 1386874-06-1 ]

17
[ 1386874-33-4 ]
[ 1386874-06-1 ]

Reference： [1]Patent: US2012/184577,2012,A1

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H200	Unstable explosive
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H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1386874-06-1 ] {[proInfo.proName]}

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[ 1386874-06-1 ] Synthesis Path-Downstream 1~17

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