[ CAS No. 749922-34-7 ] {[proInfo.proName]}

Name: 749922-34-7|7-(Benzyloxy)quinolin-4-ol|95%
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SKU: A121418
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Quality Control of [ 749922-34-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 749922-34-7 ]

SDS Specification

Alternatived Products of [ 749922-34-7 ]

Product Details of [ 749922-34-7 ]

CAS No. :	749922-34-7	MDL No. :	MFCD06659963
Formula :	C₁₆H₁₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KWQRHYWEGFFXKV-UHFFFAOYSA-N
M.W :	251.28	Pubchem ID :	21075752
Synonyms :

Calculated chemistry of [ 749922-34-7 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.06
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	74.75
TPSA :	42.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.39
Log Po/w (XLOGP3) :	3.3
Log Po/w (WLOGP) :	3.37
Log Po/w (MLOGP) :	2.25
Log Po/w (SILICOS-IT) :	3.4
Consensus Log Po/w :	2.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.9
Solubility :	0.0315 mg/ml ; 0.000125 mol/l
Class :	Soluble
Log S (Ali) :	-3.86
Solubility :	0.0343 mg/ml ; 0.000136 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.79
Solubility :	0.000405 mg/ml ; 0.00000161 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.73

Safety of [ 749922-34-7 ]

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

Application In Synthesis of [ 749922-34-7 ]

* 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 [ 749922-34-7 ]
Downstream synthetic route of [ 749922-34-7 ]

[ 749922-34-7 ] Synthesis Path-Upstream 1~6

1
[ 749922-33-6 ]
[ 749922-34-7 ]

Reference： [1] Patent: WO2005/20999, 2005, A1, . Location in patent: Page/Page column 39; 58-59
[2] Patent: WO2006/74003, 2006, A2, . Location in patent: Page/Page column 113
[3] Patent: WO2006/86449, 2006, A2, . Location in patent: Page/Page column 83
[4] Patent: US2005/54640, 2005, A1,
[5] Patent: WO2005/32484, 2005, A2, . Location in patent: Page/Page column 78-79
[6] Patent: WO2005/48933, 2005, A2, . Location in patent: Page/Page column 220-221
[7] Patent: US2004/176367, 2004, A1, . Location in patent: Page/Page column 51
[8] Patent: WO2006/9826, 2006, A1, . Location in patent: Page/Page column 50-51
[9] Patent: WO2006/28451, 2006, A1, . Location in patent: Page/Page column 111
[10] Patent: US2007/166384, 2007, A1, . Location in patent: Page/Page column 44
[11] Patent: WO2005/32484, 2005, A2, . Location in patent: Page/Page column 78-79
[12] Patent: WO2005/48933, 2005, A2, . Location in patent: Page/Page column 220-221

2
[ 909345-85-3 ]
[ 749922-34-7 ]

Yield	Reaction Conditions	Operation in experiment
48.5%	for 5 h; Reflux	Step 2) 7-(benzyloxy)quinolin-4-ol A solution of 5-((3-(Benzyloxy)phenylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (300 g, 849.8 mol) in 1,2-dichlorobenzene (3 L, Aladdin) was heated to reflux for 5 hours. The reaction mixture was cooled to room temperature, followed by further cooling in an ice bath for 2 hours. The solid was collected through filtration, stirred with MeOH (300 mL) at room temperature for 2 hours. The solid was collected through filtration and dried in vacuo at 45° C. to afford the title compound as a pale solid (103 g, 48.5percent). MS (ESI, pos. ion) m/z: 252.2 [M+1]; ¹H NMR (400 MHz, DMSO-d₆): δ 5.23 (s, 2H), 5.98 (d, J=7.2 Hz, 1H), 7.02 (t, 2H), 7.41 (t, 1H), 7.45 (t, J=6.8 Hz, J=7.6 Hz, 2H), 7.52 (d, J=7.6 Hz, 2H), 7.84 (t, J=6.4 Hz, J=6.0 Hz, 1H), 8.03 (d, J=9.2 Hz, 1H), 11.60 (s, 1H).

Reference： [1] Patent: US2012/219522, 2012, A1, . Location in patent: Page/Page column 20

3
[ 1484-26-0 ]
[ 749922-34-7 ]

Reference： [1] Patent: US2012/219522, 2012, A1,
[2] Patent: WO2005/32484, 2005, A2,
[3] Patent: WO2005/48933, 2005, A2,

4
[ 749922-34-7 ]
[ 178984-56-0 ]

Yield	Reaction Conditions	Operation in experiment
91.6%	With trichlorophosphate In toluene at 120℃; for 1 h;	Step 3) 7-(benzyloxy)-4-chloroquinoline To a suspension of 7-(benzyloxy)quinolin-4-ol (72 g, 287 mmol) in toluene (134 mL) was added phosphoryl trichloride (44 g, 287 mmol, Tianjin FuChen Chem. Co. Ltd.). The suspension was heated to 120° C. for 1 hour. The reaction mixture was then cooled to 70° C. and diluted with EtOAc (600 mL). The resulted mixture was stirred for 30 minutes while cooling down to 15° C. using an ice bath. The mixture was neutralized with 3 M NaOH aqueous solution to pH 7~8 while maintaining the temperature of the solution under 20° C. The aqueous layer was separated and extracted with EtOAc (200 mL). The combined organic layers were washed with brine (200 mL), dried over anhydrous Na₂SO₄ and concentrated in vacuo to give the title compound as a pale yellow solid (70.8 g, 91.6percent). MS (ESI, pos. ion) m/z: 270.1 [M+1]; ¹H NMR (400 MHz, DMSO-d₆): δ 5.31 (s, 2H), 7.35 (t, 1H), 7.42 (t, J=7.2 Hz, J=7.6 Hz, 2H), 7.47 (dd, J=2.8 Hz, J=9.2 Hz, 1H), 7.52 (d, J=7.6 Hz, 2H), 7.13 (t, J=4.8 Hz, J=4.0 Hz, 2H), 8.11 (d, J=9.6 Hz, 1H), 8.75 (d, J=4.8 Hz, 1H).

Reference： [1] Patent: US2012/219522, 2012, A1, . Location in patent: Page/Page column 20

5
[ 749922-34-7 ]
[ 178984-56-0 ]

Reference： [1] Patent: EP1724268, 2006, A1, . Location in patent: Page/Page column 83

6
[ 749922-34-7 ]
[ 1394820-98-4 ]

Reference： [1] Patent: US2012/219522, 2012, A1,

[ 749922-34-7 ] Synthesis Path-Downstream 1~73

1
[ 749922-34-7 ]
[ 749922-35-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	With nitric acid; In propionic acid; at 125℃; for 3.0h;	Concentrated nitric acid (70% content, 1 .5 eq) was very slowly added to a solution of C4 in propionic acid (0.37 M) heated to 125 C. The reaction mixture was stirred 3 h at 125 C, allowed to cool to rt and filtered on filter paper. The collected solid was rinsed with water and dried under vacuum to give C5 in 74% yield.
	With nitric acid; In water; propionic acid; at 121 - 125℃; for 1.5h;	A mixture of <strong>[749922-34-7]7-benzyloxyquinolin-4-ol</strong> (71.47 g, 0. 2844 mol) and propionic acid (700 mL) was heated to 125 C with vigorous stirring. Nitric acid (23.11 mL of 16 M) was slowly added over a period of 30 minutes while maintaining the reaction temperature between 121 C and 125 C. After the addition, the reaction was stirred at 125 C for 1 hour then allowed to cool to ambient temperature. The resulting solid was isolated by filtration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7- BENZYLOXY-3-NITROQUINOLIN-4-OL as a grayish powder. H NMR (300MHZ, DMSO-D6) : 8 12.77 (s, 1H), 9.12 (s, 1H), 8.17 (dd, J= 3.3, 6.3Hz, 1H), 7.51-7. 33 (m, 5H), 7.21-7. 17 (m, 2H), 5. 25 (s, 2H).
	With nitric acid; propionic acid; at 121 - 125℃; for 1.5h;	Part C; A mixture of <strong>[749922-34-7]7-benzyloxyquinolin-4-ol</strong> (71.47 g, 0.2844 mol) and propionic acid(700 niL) was heated to 125 0C with vigorous stirring. Nitric acid (23.11 mL of 16 M) was slowly added over a period of 30 minutes while maintaining the reaction temperature between 121 0C and 125 0C. After the addition, the reaction was stirred at 125 0C for 1 hour then allowed to cool to ambient temperature. The resulting solid was isolated by filtration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7- benzyloxy-3-nitroquinolin-4-ol as a grayish powder.1H NMR (300MHz, DMSCU5) : delta 12.77 (s, IH), 9.12 (s, IH), 8.17 (dd, J= 3.3, 6.3Hz, IH), 7.51-7.33 (m, 5H), 7.21-7.17 (m, 2H), 5.25 (s, 2H).

	With nitric acid; In propionic acid; at 121 - 125℃; for 1.5h;	A mixture of <strong>[749922-34-7]7-benzyloxyquinolin-4-ol</strong> (71.47 g, 0.2844 mol) and propionic acid (700 mL) was heated to 125 C with vigorous stirring. Nitric acid (23.11 mL of 16 molar (M)) was slowly added over a period of 30 minutes while maintaining the reaction temperature between 121 C and 125 0C. After the addition, the reaction was stirred at 125 0C for one hour then allowed to cool to room temperature. The resulting solid was isolated by filtration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7-benzyloxy-3-nitroquinolin-4-ol as a grayish powder. 1H NMR (300MHz, DMSO-40 delta 12.77 (s, IH), 9.12 (s, IH), 8.17 (dd, J= 3.3, 6.3Hz, IH)5 7.51-7.33 (m, 5H)5 7.21-7.17 (m, 2H)5 5.25 (s, 2H). Material from a separate run was used in the next step.
	With nitric acid; propionic acid; at 121 - 125℃; for 1.5h;	A mixture of <strong>[749922-34-7]7-benzyloxyquinolin-4-ol</strong> (71.47 g, 0.2844 mol) and propionic acid (700 niL) was heated to 125 0C with vigorous stirring. Nitric acid (23.11 niL of 16 molar (M)) was slowly added over a period of 30 minutes while maintaining the reaction temperature between 121 0C and 125 0C. After the addition, the reaction was stirred at 125 0C for 1 hour then allowed to cool to ambient temperature. The resulting solid was isolated by filtration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7-benzyloxy-3-nitroquinolin-4-ol as a grayish powder. 1H NMR (300MHz, DMSO-cfc) : delta 12.77 (s, IH), 9.12 (s, IH), 8.17 (dd, J= 3.3, 6.3Hz, IH), 7.51-7.33 (m, 5H), 7.21-7.17 (m, 2H), 5.25 (s, 2H).
	With nitric acid; propionic acid;	Part C A mixture of <strong>[749922-34-7]7-benzyloxyquinolin-4-ol</strong> (71.47 g, 0.2844 mol) and propionic acid (700 mL) was heated to 125 C. with vigorous stirring. Nitric acid (23.11 mL of 16 M) was slowly added over a period of 30 minutes while maintaining the reaction temperature between 121 C. and 125 C. After the addition, the reaction was stirred at 125 C. for 1 hour then allowed to cool to ambient temperature. The resulting solid was isolated by filtration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7-benzyloxy-3-nitroquinolin-4-ol as a grayish powder.
	With nitric acid; propionic acid;	Part C A mixture of <strong>[749922-34-7]7-benzyloxyquinolin-4-ol</strong> (71.47 g, 0.2844 mol) and propionic acid (700 mL) was heated to 125 C. with vigorous stirring. Nitric acid (23.11 mL of 16 M) was slowly added over a period of 30 minutes while maintaining the reaction temperature between 121 C. and 125 C. After the addition, the reaction was stirred at 125 C. for 1 hour then allowed to cool to ambient temperature. The resulting solid was isolated by filtration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7-benzyloxy-3-nitroquinolin-4-ol as a grayish powder. 1H NMR (300 MHz, DMSO-d6) delta 12.77 (s, 1H), 9.12 (s, 1H), 8.17 (dd, J=6.3, 3.3 Hz, 1H), 7.51-7.33 (m, 5H), 7.21-7.17 (m, 2H), 5.25 (s, 2H).
	With nitric acid; In water; propionic acid; at 121 - 125℃; for 1.5h;	Part C A mixture of <strong>[749922-34-7]7-benzyloxyquinolin-4-ol</strong> (71.47 g, 0.2844 mol) and propionic acid (700 ML) was heated to 125 C. with vigorous stirring.nitric acid (23.11 ML of 16 M) was slowly added over a period of 30 minutes while maintaining the reaction temperature between 121 C. and 125 C. After the addition, the reaction was stirred at 125 C. for 1 hour then allowed to cool to ambient temperature.The resulting solid was isolated by filtration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7-benzyloxy-3-nitroquinolin-4-ol as a grayish powder. 1H NMR (300 MHz, DMSO-d6) delta 12.77 (s, 1H), 9.12 (s, 1H), 8.17 (dd, J=6.3, 3.3 Hz, 1H), 7.51-7.33 (m, 5H), 7.21-7.17 (m, 2H), 5.25 (s, 2H).
		PartC; A mixture of <strong>[749922-34-7]7-benzyloxyquinolin-4-ol</strong> (71.47 g, 0.2844 mol) and propionic acid(700 mL) was heated to 125 C with vigorous stirring. Nitric acid (23.11 mL of 16 M)was slowly added over a period of 30 minutes while maintaining the reaction temperaturebetween 121 C and 125 C. After the addition, the reaction was stirred at 125 C for 1hour then allowed to cool to ambient temperature. The resulting solid was isolated byfiltration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7-benzyloxy-3-nitroquinolin-4-ol as a grayish powder. .H NMR (300MHz, DMSO-d6) 5 12.77 (s, 1H), 9.12 (s, 1H), 8.17 (dd, J= 3.3, 6.3Hz, 1H), 7.51-7.33 (m, 5H), 7.21-7.17(m,2H), 5.25(s,2H).
	With nitric acid; In propionic acid; at 121 - 125℃; for 1.5h;	Part C; A mixture of <strong>[749922-34-7]7-benzyloxyquinolin-4-ol</strong> (71.47 g, 0.2844 mol) and propionic acid (700 mL) was heated to 125 0C with vigorous stirring. Nitric acid (23.11 mL of 16 M) was slowly added over a period of 30 minutes while maintaining the reaction temperature between 121 0C and 125 0C. After the addition, the reaction was stirred at 125 0C for 1 hour then allowed to cool to ambient temperature. The resulting solid was isolated by filtration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7- benzyloxy-3-nitroquinolin-4-ol as a grayish powder. 1H NMR (300 MHz, DMSO-J15) delta 12.77 (s, IH), 9.12 (s, IH), 8.17 (dd, J= 6.3, 3.3 Hz, IH), 7.51-7.33 (m, 5H), 7.21-7.17 (m, 2H), 5.25 (s, 2H).
	With nitric acid; In propionic acid; at 121 - 125℃; for 1.5h;	A mixture of <strong>[749922-34-7]7-benzyloxyquinolin-4-ol</strong> (71.47 g, 0.2844 mol) and propionic acid (700 mL) was heated to 125 C. with vigorous stirring. Nitric acid (23.11 mL of 16 molar (M)) was slowly added over a period of 30 minutes while maintaining the reaction temperature between 121 C. and 125 C. After the addition, the reaction was stirred at 125 C. for 1 hour then allowed to cool to ambient temperature. The resulting solid was isolated by filtration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7-benzyloxy-3-nitroquinolin-4-ol as a grayish powder.
	With nitric acid; In water; propionic acid; at 121 - 125℃; for 1.5h;	A mixture of <strong>[749922-34-7]7-benzyloxyquinolin-4-ol</strong> (71.47 g, 0.2844 mol) and propionic acid (700 mL) was heated to 125 C with vigorous stirring. Nitric acid (23.11 mL of 16 M) was slowly added over a period of 30 minutes while maintaining the reaction temperature between 121 C and 125 C. After the addition, the reaction was stirred at 125 C for 1 hour then allowed to cool to ambient temperature. The resulting solid was isolated by filtration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7- benzyloxy-3-nitroquinolin-4-ol as a grayish powder. H NMR (300 MHz, DMSO-d6) 5 12.77 (s, 1H), 9.12 (s, 1H), 8.17 (dd, J= 6.3, 3.3 Hz, 1H), 7.51-7. 33 (M, 5H), 7.21-7. 17 (M, 2H), 5.25 (s, 2H).
	With nitric acid; In propionic acid; at 121 - 125℃; for 1.5h;	A mixtureof <strong>[749922-34-7]7-benzyloxyquinolin-4-ol</strong> (71.47 g, 0.2844 mol) and propionic acid (700 mL) was heated to125 C with vigorous stirring. Nitric acid (23.11 mL of 16 M) was slowly added over a period of 30 minutes while maintaining the reaction temperature between121 C and125 C. After the addition, the reaction was stirred at125 C for 1 hour then allowed to cool to ambient temperature. The resulting solid was isolated by filtration, washed with water, and dried in an oven for 1.5 days to provide 69.13 g of 7- benzyloxy-3-nitroquinolin-4-ol as a grayish powder. 'H NMR (300MHz, DMSO-d6) : 6 12.77 (s, 1H), 9.12 (s, 1H), 8.17 (dd, J= 3.3, 6.3Hz, 1H), 7.51-7. 33 (m, 5H), 7.21-7. 17 (m, 2H), 5.25 (s, 2H).

Reference： [1]Patent: WO2018/46460,2018,A1 .Location in patent: Page/Page column 31; 32
[2]Patent: WO2005/20999,2005,A1 .Location in patent: Page/Page column 39; 59
[3]Patent: WO2006/74003,2006,A2 .Location in patent: Page/Page column 114
[4]Patent: WO2006/86449,2006,A2 .Location in patent: Page/Page column 83
[5]Patent: WO2006/86633,2006,A2 .Location in patent: Page/Page column 62
[6]Patent: US2004/258698,2004,A1
[7]Patent: US2005/54640,2005,A1
[8]Patent: US2004/176367,2004,A1 .Location in patent: Page/Page column 51
[9]Patent: WO2006/9826,2006,A1 .Location in patent: Page/Page column 51
[10]Patent: WO2006/28451,2006,A1 .Location in patent: Page/Page column 111
[11]Patent: US2007/166384,2007,A1 .Location in patent: Page/Page column 44-45
[12]Patent: WO2005/32484,2005,A2 .Location in patent: Page/Page column 79
[13]Patent: WO2005/48933,2005,A2 .Location in patent: Page/Page column 221

2
[ 749922-33-6 ]
[ 749922-34-7 ]

Yield	Reaction Conditions	Operation in experiment
	at 100 - 210℃; for 1.66667h;DOWTHERM A heat transfer fluid;	A mixture of 5-F [ (3-BENZYLOXY) phenylimino] methyl}-2, 2-dimethyl- [1, 3]-dioxane- 4,6-dione (170.65 g, 0.483 mol) and DOWTHERM A heat transfer fluid (800 ML) was heated to 100 C and then slowly added to a flask containing DOWTHERM A heat transfer fluid (1.3 L, heated at 210 C) over a period of 40 minutes. During the addition, the reaction temperature was not allowed to fall below 207 C. Following the addition, the reaction was stirred at 210 C for one hour, and then allowed to cool to ambient temperature. A precipitate formed, which was isolated by filtration, washed with diethyl ether (1.7 L) and acetone (0.5 L), and dried in an oven to provide 76.5 g OF 7- benzyloxyquinolin-4-ol as a tan powder. 1H NMR (300MHZ, DMSO-d6) : 8 11.53 (s, 1H), 7.99 (dd, J= 2.4, 7.4Hz, 1H), 7.79 (d, J = 7.4Hz, 1H), 7.50-7. 32 (m, 5H), 7.00 (s, 1H), 6.98 (dd, J= 2.5, 7.4Hz, 1H), 5.93 (d, J= 7. 5HZ, 1H), 5. 20 (s, 2H).
	With DOWTHERM A heat transfer fluid; at 100 - 210℃; for 1.66667h;	Part B; A mixture of 5 - { [(3 -benzyloxy)phenylimino]methyl } -2,2-dimethyl- [1,3] -dioxane-4,6-dione (170.65 g, 0.483 mol) and DOWTHERM A heat transfer fluid (800 mL) was heated to 100 0C and then slowly added to a flask containing DOWTHERM A heat transfer fluid (1.3 L, heated at 210 0C) over a period of 40 minutes. During the addition, the reaction temperature was not allowed to fall below 207 0C. Following the addition, the reaction was stirred at 210 0C for one hour, and then allowed to cool to ambient temperature. A precipitate formed, which was isolated by filtration, washed with diethyl ether (1.7 L) and acetone (0.5 L), and dried in an oven to provide 76.5 g of 7- benzyloxyquinolin-4-ol as a tan powder. EPO <DP n="115"/>1H NMR (300MHz, OMSO-d6) : delta 11.53 (s, IH), 7.99 (dd, J= 2.4, 7.4Hz, IH), 7.79 (d, J = 7.4Hz, IH), 7.50-7.32 (m, 5H), 7.00 (s, IH), 6.98 (dd, J= 2.5, 7.4Hz, IH), 5.93 (d, J= 7.5Hz, IH), 5.20 (s, 2H).
	With DOWTHERM A heat transfer fluid; at 100 - 210℃; for 1.66667h;	A mixture of 5 - { [(3 -benzyloxy)phenylimino]methyl } -2,2-dimethyl-[l ,3] -dioxane- 4,6-dione (170.65 g, 0.483 mol) and DOWTHERM A (800 mL) heat transfer fluid was heated to 100 C and then slowly added to a flask containing DOWTHERM A (1.3 liters (L), heated at 210 0C) heat transfer fluid over a period of 40 minutes. During the addition, the reaction temperature was not allowed to fall below 207 0C. Following the addition, the reaction was stirred at 210 C for one hour, and then allowed to cool to ambient temperature. A precipitate formed, which was isolated by filtration, washed sequentially with diethyl ether (1.7 L) and acetone (0.5 L), and dried in an oven to provide 76.5 g of 7- benzyloxyquinolin-4-ol as a tan powder. 1H NMR (300MHz, DMSO-cfe) delta 11.53 (s, IH), 7.99 (dd, J= 2.4, 7.4 Hz, IH), 7.79 (d, J= 7.4 Hz, IH), 7.50-7.32 (m, 5H), 7.00 (s, IH), 6.98 (dd, J= 2.5, 7.4 Hz, IH), 5.93 (d, J= 7.5Hz, IH), 5.20 (s, 2H).

		Part B A mixture of 5-[(3-benzyloxy)phenylimino]methyl}-2,2-dimethyl-1,3-dioxane-4,6-dione (170.65 g, 0.483 mol) and DOWTHERM A heat transfer fluid (800 mL) was heated to 100 C. and then slowly added to a flask containing DOWTHERM A heat transfer fluid (1.3 L, heated at 210 C.) over a period of 40 minutes. During the addition, the reaction temperature was not allowed to fall below 207 C. Following the addition, the reaction was stirred at 210 C. for one hour, and then allowed to cool to ambient temperature. A precipitate formed, which was isolated by filtration, washed with diethyl ether (1.7 L) and acetone (0.5 L), and dried in an oven to provide 76.5 g of 7-benzyloxyquinolin-4-ol as a tan powder. 1H NMR (300 MHz, DMSO-d6) delta 11.53 (s, 1H), 7.99 (dd, J=7.4, 2.4 Hz, 1H), 7.79 (d, J=7.4 Hz, 1H), 7.50-7.32 (m, 5H), 7.00 (s, 11H), 6.98 (dd, J=7.4, 2.5 Hz, 1H), 5.93 (d, J=7.5 Hz, 1H), 5.20 (s, 2H).
	at 207 - 210℃; for 1.66667h;Mixed with DOWTHERM A heat transfer fluid;	Part B A mixture of 5-[(3-benzyloxy)phenylimino]methyl}-2,2-dimethyl-1,3-dioxane-4,6-dione (170.65 g, 0.483 mol) and DOWTHERM A heat transfer fluid (800 ML) was heated to 100 C. and then slowly added to a flask containing DOWTHERM A heat transfer fluid (1.3 L, heated at 210 C.) over a period of 40 minutes.During the addition, the reaction temperature was not allowed to fall below 207 C. Following the addition, the reaction was stirred at 210 C. for one hour, and then allowed to cool to ambient temperature.A precipitate formed, which was isolated by filtration, washed with diethyl ether (1.7 L) and acetone (0.5 L), and dried in an oven to provide 76.5 g of 7-benzyloxyquinolin-4-ol as a tan powder. 1H NMR (300 MHz, DMSO-d6) delta 11.53 (s, 1H), 7.99 (dd, J=7.4, 2.4 Hz, 1H), 7.79 (d, J=7.4 Hz, 1H), 7.50-7.32 (m, 5H), 7.00 (s, 1H), 6.98 (dd, J=7.4, 2.5 Hz, 1H), 5.93 (d, J=7.5 Hz, 1H), 5.20 (s, 2H).
	In diphenyl ether-biphenyl eutectic; at 100 - 210℃; for 1.66667h;	PartB; A mixture of 5-[(3-benzyloxy)phenylimino]methyl}-2,2-dimethyl-[l,3]-dioxane-4,6-dione (170.65 g, 0.483 mol) and DOWTHERM A (800 mL) was heated to 100 C andthen slowly added to a flask containing DOWTHERM A (1.3 L, heated at 210 C) over aperiod of 40 minutes. During the addition, the reaction temperature was not allowed tofall below 207 C. Following the addition, the reaction was stirred at 210 C for one hour,and then allowed to cool to ambient temperature. A precipitate formed, which wasisolated by filtration, washed with diethyl ether (1.7 L) and acetone (0.5 L), and dried inan oven to provide 76.5 g of 7-benzyloxyquinolin-4-ol as a tan powder. *H NMR(300MHz, DMSO-4?) 5 11.53(s, 1H), 7.99 (dd, J=2A, 7.4 Hz, 1H), 7.79 (d, J= 7.4 Hz,1H), 7.50-7.32 (m, 5H), 7.00 (s, 1H), 6.98 (dd,J= 2.5, 7.4 Hz, 1H), 5.93 (d,J= 7.5Hz,1H), 5.20 (s, 2H).
	In diphenyl ether-biphenyl eutectic; at 100 - 210℃; for 1.66667h;	Part B; A mixture of 5-[(3-benzyloxy)phenylimino]methyl}-2,2-dimethyl-l,3-dioxane- 4,6-dione (170.65 g, 0.483 mol) and DOWTHERM A heat transfer fluid (800 mL) was heated to 1000C and then slowly added to a flask containing DOWTHERM A heat transfer fluid (1.3 L, heated at 210 0C) over a period of 40 minutes. During the addition, the reaction temperature was not allowed to fall below 207 0C. Following the addition, the reaction was stirred at 210 0C for one hour, and then allowed to cool to ambient temperature. A precipitate formed, which was isolated by filtration, washed with diethyl ether (1.7 L) and acetone (0.5 L), and dried in an oven to provide 76.5 g of 7- benzyloxyquinolin-4-ol as a tan powder. 1H NMR (300 MHz, DMSO-^) delta 11.53 (s, IH), 7.99 (dd, J= 7.4, 2.4 Hz, IH), 7.79 (d, J = 7.4 Hz, IH), 7.50-7.32 (m, 5H), 7.00 (s, IH), 6.98 (dd, J= 7.4, 2.5 Hz, IH), 5.93 (d, J= 7.5 Hz, IH), 5.20 (s, 2H).
	In diphenyl ether-biphenyl eutectic; at 100 - 210℃; for 1.66667h;	A mixture of 5-[(3-benzyloxy)phenylimino]methyl}-2,2-dimethyl-[1,3]-dioxane-4,6-dione (170.65 g, 0.483 mol) and DOWTHERM A (800 mL) was heated to 100 C. and then slowly added to a flask containing DOWTHERM A (1.3 L, heated at 210 C.) over a period of 40 minutes. During the addition, the reaction temperature was not allowed to fall below 207 C. Following the addition, the reaction was stirred at 210 C. for one hour, and then allowed to cool to ambient temperature. A precipitate formed, which was isolated by filtration, washed with diethyl ether (1.7 L) and acetone (0.5 liter (L)), and dried in an oven to provide 76.5 grams (g) of 7-benzyloxyquinolin-4-ol as a tan powder.
	With dowtherm A; at 100 - 210℃; for 1.66667h;	A mixture of 5- { [ (3-BENZYLOXY) phenylimino] METHYL}-2, 2-DIMETHYL- [ 1, 3] -dioxane- 4,6-dione (170.65 g, 0.483 mol) and DOWTHERM A heat transfer fluid (800 mL) was heated to 100 C and then slowly added to a flask containing DOWTHERM A heat transfer fluid (1.3 L, heated at 210 C) over a period of 40 minutes. During the addition, the reaction temperature was not allowed to fall below 207 C. Following the addition, the reaction was stirred at 210 C for one hour, and then allowed to cool to ambient temperature. A precipitate formed, which was isolated by filtration, washed with diethyl ether (1.7 L) and acetone (0.5 L), and dried in an oven to provide 76.5 g of 7- benzyloxyquinolin-4-ol as a tan powder. IH NMR (300 MHz, DMSO-d6) 6 11.53 (s, 1H), 7.99 (dd, J= 7.4, 2.4 Hz, 1H), 7.79 (d, J = 7.4 Hz, 1H), 7.50-7. 32 (M, 5H), 7.00 (s, 1H), 6.98 (dd, J= 7.4, 2.5 Hz, 1H), 5.93 (d, J= 7.5 Hz, 1H), 5.20 (s, 2H).
	In DOWTHERM A heat transfer fluid; at 100 - 210℃; for 1.66667h;	A mixture of5-1 [ (3-benzyloxy) phenylimino]methyl}-2,2-dimethyl- [1, 3] -dioxane- 4,6-dione (170.65 g, 0.483 mol) and DOWTHERM A heat transfer fluid (800 mL) was heated to100 C and then slowly added to a flask containing DOWTHERM A heat transfer fluid (1.3 L, heated at210 C) over a period of 40 minutes. During the addition, the reaction temperature was not allowed to fall below207 C. Following the addition, the reaction was stirred at210 C for one hour, and then allowed to cool to ambient <Desc/Clms Page number 221>temperature. A precipitate formed, which was isolated by filtration, washed with diethyl ether (1.7 L) and acetone (0.5 L), and dried in an oven to provide 76.5 g of 7- benzyloxyquinolin-4-ol as a tan powder. 1H NMR (300MHz, DMSO-d6) : 8 11.53 (s, 1H), 7.99 (dd, J= 2. 4,7. 4Hz, 1H), 7.79 (d, J = 7.4Hz, 1H), 7.50-7. 32 (m, 5H), 7.00 (s, 1H), 6.98 (dd, J= 2.5, 7.4Hz, 1H), 5.93 (d, J= 7. 5Hz, 1H), 5.20 (s, 2H).

Reference： [1]Patent: WO2005/20999,2005,A1 .Location in patent: Page/Page column 39; 58-59
[2]Patent: WO2006/74003,2006,A2 .Location in patent: Page/Page column 113
[3]Patent: WO2006/86449,2006,A2 .Location in patent: Page/Page column 83
[4]Patent: US2005/54640,2005,A1
[5]Patent: US2004/176367,2004,A1 .Location in patent: Page/Page column 51
[6]Patent: WO2006/9826,2006,A1 .Location in patent: Page/Page column 50-51
[7]Patent: WO2006/28451,2006,A1 .Location in patent: Page/Page column 111
[8]Patent: US2007/166384,2007,A1 .Location in patent: Page/Page column 44
[9]Patent: WO2005/32484,2005,A2 .Location in patent: Page/Page column 78-79
[10]Patent: WO2005/48933,2005,A2 .Location in patent: Page/Page column 220-221

3
[ 749922-34-7 ]
[ 178984-56-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; trichlorophosphate; at 120℃; for 0.5h;	3-Benzyloxy-aniline (1.0 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxan-4,6-dione (1.03 g) were suspended in 2-propanol (15 ml) and the suspension was stirred at 70C for 3 hr. The reaction mixture was cooled to room temperature, was filtered, and was washed with ether. The residue as such was used in the next reaction without purification. The residue and biphenyl (4.34 g) were suspended in diphenyl ether (12 ml), and the suspension was stirred at 240C overnight. The reaction mixture was cooled to room temperature, and the cooled reaction mixture as such was applied to column chromatography with a methanol-chloroform system. The crude product as such was used in the next reaction without further purification. The crude product was suspended in diisopropylethylamine (7 ml), phosphorus oxychloride (1.5 ml) was added to the suspension, and the mixture was stirred at 120C for 30 min. Water was added to the reaction mixture under ice cooling. The aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an ethyl acetate-hexane system to give 7-benzyloxy-4-chloro-quinoline (222 mg, yield 16%) (3 steps).

Reference： [1]Patent: EP1724268,2006,A1 .Location in patent: Page/Page column 83

4
5-[(E)-[3-(benzyloxy)phenyl]imino}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione [ No CAS ]
[ 749922-34-7 ]

Yield	Reaction Conditions	Operation in experiment
	at 210℃; for 1.66667h;	A mixture of 5-[(3-benzyloxy)phenylimino]methyl}-2,2-dimethyl-[l,3]-dioxane- 4,6-dione (170.65 g, 0.483 mol) and DOWTHERM A heat transfer fluid (800 mL) was heated to 100 0C and then slowly added to a flask containing DOWTHERM A heat transfer fluid (1.3 liters (L), heated at 210 0C) over a period of 40 minutes. During the addition, the reaction temperature was not allowed to fall below 207 0C. Following the addition, the reaction was stirred at 210 0C for one hour, and then allowed to cool to ambient temperature. A precipitate formed, which was isolated by filtration, washed with diethyl ether (1.7 L) and acetone (0.5 L), and dried in an oven to provide 76.5 g of 7- benzyloxyquinolin-4-ol as a tan powder.1H NMR (300MHz, DMSO-cfc) : delta 11.53 (s, IH), 7.99 (dd, J= 2.4, 7.4Hz, IH), 7.79 (d, J = 7.4Hz, IH), 7.50-7.32 (m, 5H), 7.00 (s, IH), 6.98 (dd, J= 2.5, 7.4Hz, IH), 5.93 (d, J= 7.5Hz, IH), 5.20 (s, 2H).

Reference： [1]Patent: WO2006/86633,2006,A2 .Location in patent: Page/Page column 61

Yield	Reaction Conditions	Operation in experiment
		Part B A mixture of 5-[(3-benzyloxy)phenylimino]methyl}-2,2-dimethyl-[1,3]-dioxane-4,6-dione (170.65 g, 0.483 mol) and DOWTHERM A (800 mL) was heated to 100 C. and then slowly added to a flask containing DOWTHERM A (1.3 L, heated at 210 C.) over a period of 40 minutes. During the addition, the reaction temperature was not allowed to fall below 207 C. Following the addition, the reaction was stirred at 210 C. for one hour, and then allowed to cool to ambient temperature. A precipitate formed, which was isolated by filtration, washed with diethyl ether (1.7 liters (L)) and acetone (0.5 L), and dried in an oven to provide 76.5 grams (g) of 7-benzyloxyquinolin-4-ol as a tan powder.

6
[ 1484-26-0 ]
[ 749922-34-7 ]

Reference： [1]Patent: US2012/219522,2012,A1
[2]Patent: WO2005/32484,2005,A2
[3]Patent: WO2005/48933,2005,A2
[4]Patent: CN110845406,2020,A

7
[ 749922-34-7 ]
[ 1221443-46-4 ]

Reference： [1]Patent: US2012/219522,2012,A1

8
[ 749922-34-7 ]
[ 1394820-97-3 ]

Reference： [1]Patent: US2012/219522,2012,A1

9
[ 749922-34-7 ]
[ 1394820-98-4 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394820-99-5 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394820-70-2 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-01-2 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394820-83-7 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-02-3 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-03-4 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-04-5 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-05-6 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394820-85-9 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-06-7 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-07-8 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394820-87-1 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-08-9 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-09-0 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394820-91-7 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-10-3 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-11-4 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-12-5 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
[ 1394821-13-6 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 909345-85-3 ]
[ 749922-34-7 ]

Yield	Reaction Conditions	Operation in experiment
48.5%	In 1,2-dichloro-benzene; for 5.0h;Reflux;	Step 2) 7-(benzyloxy)quinolin-4-ol A solution of 5-((3-(Benzyloxy)phenylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (300 g, 849.8 mol) in 1,2-dichlorobenzene (3 L, Aladdin) was heated to reflux for 5 hours. The reaction mixture was cooled to room temperature, followed by further cooling in an ice bath for 2 hours. The solid was collected through filtration, stirred with MeOH (300 mL) at room temperature for 2 hours. The solid was collected through filtration and dried in vacuo at 45 C. to afford the title compound as a pale solid (103 g, 48.5%). MS (ESI, pos. ion) m/z: 252.2 [M+1]; 1H NMR (400 MHz, DMSO-d6): delta 5.23 (s, 2H), 5.98 (d, J=7.2 Hz, 1H), 7.02 (t, 2H), 7.41 (t, 1H), 7.45 (t, J=6.8 Hz, J=7.6 Hz, 2H), 7.52 (d, J=7.6 Hz, 2H), 7.84 (t, J=6.4 Hz, J=6.0 Hz, 1H), 8.03 (d, J=9.2 Hz, 1H), 11.60 (s, 1H).
48%	With 1,2-dichloro-benzene; at 180℃; for 5.0h;	To a 1 L reaction bottle, sequentially add o-dichlorobenzene (500 mL), compound 1 (50.0 g), stir to warm to 180C and hold for 5 hours, TLC detection reaction. After the reaction was completed, the temperature was slowly lowered to 20 C, stirred for 2h, and filtered to obtain a solid. The resulting solid was slurried with DCM (100 mL) at 20-30 C for 2 hours, filtered, and dried to give compound 2 (18.3 g, 48%).

Reference： [1]Patent: US2012/219522,2012,A1 .Location in patent: Page/Page column 20
[2]Patent: CN110845406,2020,A .Location in patent: Paragraph 0074-0078

30
[ 749922-34-7 ]
[ 178984-56-0 ]

Yield	Reaction Conditions	Operation in experiment
91.6%	With trichlorophosphate; In toluene; at 120℃; for 1h;	Step 3) 7-(benzyloxy)-4-chloroquinoline To a suspension of 7-(benzyloxy)quinolin-4-ol (72 g, 287 mmol) in toluene (134 mL) was added phosphoryl trichloride (44 g, 287 mmol, Tianjin FuChen Chem. Co. Ltd.). The suspension was heated to 120 C. for 1 hour. The reaction mixture was then cooled to 70 C. and diluted with EtOAc (600 mL). The resulted mixture was stirred for 30 minutes while cooling down to 15 C. using an ice bath. The mixture was neutralized with 3 M NaOH aqueous solution to pH 7~8 while maintaining the temperature of the solution under 20 C. The aqueous layer was separated and extracted with EtOAc (200 mL). The combined organic layers were washed with brine (200 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a pale yellow solid (70.8 g, 91.6%). MS (ESI, pos. ion) m/z: 270.1 [M+1]; 1H NMR (400 MHz, DMSO-d6): delta 5.31 (s, 2H), 7.35 (t, 1H), 7.42 (t, J=7.2 Hz, J=7.6 Hz, 2H), 7.47 (dd, J=2.8 Hz, J=9.2 Hz, 1H), 7.52 (d, J=7.6 Hz, 2H), 7.13 (t, J=4.8 Hz, J=4.0 Hz, 2H), 8.11 (d, J=9.6 Hz, 1H), 8.75 (d, J=4.8 Hz, 1H).

Reference： [1]Patent: US2012/219522,2012,A1 .Location in patent: Page/Page column 20

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[ 749922-34-7 ]
[ 1394820-69-9 ]

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[ 749922-34-7 ]
[ 1394821-00-1 ]

Reference： [1]Patent: US2012/219522,2012,A1

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[ 749922-34-7 ]
C₆₅H₁₀₄N₅O₁₁P [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

34
[ 749922-34-7 ]
C₁₈H₂₄N₄O₃ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

35
[ 749922-34-7 ]
C₂₀H₂₈N₄O₃ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

36
[ 749922-34-7 ]
C₂₂H₃₂N₄O₅ [ No CAS ]
C₂₇H₃₈N₄O₇ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

37
[ 749922-34-7 ]
C₅₇H₉₅N₄O₁₀P [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

38
[ 749922-34-7 ]
[ 905975-23-7 ]

Reference： [1]Patent: WO2018/46460,2018,A1

39
[ 749922-34-7 ]
C₁₈H₁₉N₃O₂ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

40
[ 749922-34-7 ]
C₁₁H₁₃N₃O₂ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

41
[ 749922-34-7 ]
C₂₃H₃₀N₄O₅*(x)C₂HF₃O [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

42
[ 749922-34-7 ]
C₁₆H₁₉N₃O₂ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

43
[ 749922-34-7 ]
C₁₈H₂₅N₃O₃ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

44
[ 749922-34-7 ]
C₁₈H₂₂N₄O₅ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

45
[ 749922-34-7 ]
C₂₃H₂₅N₃O₂ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

46
[ 749922-34-7 ]
C₂₈H₃₁N₃O₄ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

47
[ 749922-34-7 ]
C₂₁H₂₄N₄O₆ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

48
[ 749922-34-7 ]
C₂₁H₂₆N₄O₄ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

49
[ 749922-34-7 ]
C₃₂H₄₀N₄O₅ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

50
[ 749922-34-7 ]
C₂₅H₃₄N₄O₅ [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

51
[ 749922-34-7 ]
C₂₉H₄₄N₄O₅Si [ No CAS ]

Reference： [1]Patent: WO2018/46460,2018,A1

52
[ 749922-34-7 ]
7-benzyloxy-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine [ No CAS ]

Reference： [1]Patent: WO2005/32484,2005,A2

53
[ 749922-34-7 ]
[ 749922-36-9 ]

Reference： [1]Patent: WO2005/32484,2005,A2
[2]Patent: WO2005/48933,2005,A2

54
[ 749922-34-7 ]
[ 847577-59-7 ]

Reference： [1]Patent: WO2005/32484,2005,A2

55
[ 749922-34-7 ]
[ 847577-53-1 ]

Reference： [1]Patent: WO2005/32484,2005,A2

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[ 749922-34-7 ]
[ 847577-52-0 ]

Reference： [1]Patent: WO2005/32484,2005,A2

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[ 749922-34-7 ]
[ 847577-56-4 ]

Reference： [1]Patent: WO2005/32484,2005,A2

58
[ 749922-34-7 ]
[ 847574-58-7 ]

Reference： [1]Patent: WO2005/32484,2005,A2

59
[ 749922-34-7 ]
[ 847577-54-2 ]

Reference： [1]Patent: WO2005/32484,2005,A2

60
[ 749922-34-7 ]
C₂₄H₂₇N₃O₂ [ No CAS ]

Reference： [1]Patent: WO2005/32484,2005,A2

61
[ 749922-34-7 ]
[ 850069-25-9 ]

Reference： [1]Patent: WO2005/32484,2005,A2

62
[ 749922-34-7 ]
[ 850068-91-6 ]

Reference： [1]Patent: WO2005/32484,2005,A2

63
[ 749922-34-7 ]
[ 850056-97-2 ]

Reference： [1]Patent: WO2005/32484,2005,A2

64
[ 749922-34-7 ]
[ 847578-83-0 ]

Reference： [1]Patent: WO2005/48933,2005,A2

65
[ 749922-34-7 ]
[ 847578-82-9 ]

Reference： [1]Patent: WO2005/48933,2005,A2

66
[ 749922-34-7 ]
[ 847578-84-1 ]

Reference： [1]Patent: WO2005/48933,2005,A2

67
[ 749922-34-7 ]
C₂₅H₂₇ClN₄O₄ [ No CAS ]

Reference： [1]Patent: WO2005/48933,2005,A2

68
[ 749922-34-7 ]
[ 852802-33-6 ]

Reference： [1]Patent: WO2005/48933,2005,A2

69
[ 749922-34-7 ]
[ 852802-35-8 ]

Reference： [1]Patent: WO2005/48933,2005,A2

70
[ 749922-34-7 ]
[ 852801-93-5 ]

Reference： [1]Patent: WO2005/48933,2005,A2

71
[ 749922-34-7 ]
[ 852802-34-7 ]

Reference： [1]Patent: WO2005/48933,2005,A2

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[ 749922-34-7 ]
acetone O-[4-amino-1-(2-aminoethyl)-7-(benzyloxy)-1H-imidazo[4,5-c]quinolin-2-yl]methyl}oxime tris(trifluoroacetate) [ No CAS ]

Reference： [1]Patent: WO2005/48933,2005,A2

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[ 749922-34-7 ]
[ 369-34-6 ]
[ 1394820-97-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 85℃;	DMF (140mL), 3,4-difluoro-nitrobenzene (90.0g), compound 2 (140.0g) and DIPEA (88.0g) were added to the 1L reaction bottle in turn, and the temperature was raised to 85C with stirring, and the reaction was allowed to proceed overnight After that, the reaction was detected by TLC. After the reaction was completed, the temperature was lowered to below 20C, water (420 mL) was added to the temperature controlled below 30 C, filtered, ethanol (140 mL) was added to the solid, stirred at 60C for 1 h, slowly cooled to room temperature and stirred for 30 min, filtered, and dried at 60 C Compound 3 (190.0 g, 95%) was obtained.

Reference： [1]Patent: CN110845406,2020,A .Location in patent: Paragraph 0079-0083

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
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P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
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. 749922-34-7 ] {[proInfo.proName]}

Quality Control of [ 749922-34-7 ]

Related Doc. of [ 749922-34-7 ]

Product Details of [ 749922-34-7 ]

Calculated chemistry of [ 749922-34-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 749922-34-7 ]

Application In Synthesis of [ 749922-34-7 ]

[ 749922-34-7 ] Synthesis Path-Upstream 1~6

[ 749922-34-7 ] Synthesis Path-Downstream 1~73

Related Functional Groups of [ 749922-34-7 ]

Aryls

Ethers

Alcohols

Related Parent Nucleus of [ 749922-34-7 ]

Quinolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 749922-34-7 ]

Related Parent Nucleus of
[ 749922-34-7 ]