[ CAS No. 22246-13-5 ] {[proInfo.proName]}

Name: 22246-13-5|6-Amino-3,4-dihydroquinolin-2(1H)-one|97%
Brand: Ambeed
SKU: A181670
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Quality Control of [ 22246-13-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 22246-13-5 ]

Product Details of [ 22246-13-5 ]

CAS No. :	22246-13-5	MDL No. :	MFCD00559318
Formula :	C₉H₁₀N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NFWVCYWFUIFIKU-UHFFFAOYSA-N
M.W :	162.19	Pubchem ID :	4912759
Synonyms :

Calculated chemistry of [ 22246-13-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.95
TPSA :	55.12 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) :	-6.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.25
Log Po/w (XLOGP3) :	0.66
Log Po/w (WLOGP) :	0.59
Log Po/w (MLOGP) :	0.84
Log Po/w (SILICOS-IT) :	1.37
Consensus Log Po/w :	0.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.63
Solubility :	3.79 mg/ml ; 0.0234 mol/l
Class :	Very soluble
Log S (Ali) :	-1.39
Solubility :	6.55 mg/ml ; 0.0404 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.8
Solubility :	0.258 mg/ml ; 0.00159 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.46

Safety of [ 22246-13-5 ]

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 [ 22246-13-5 ]

* 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.

Upstream synthesis route of [ 22246-13-5 ]
Downstream synthetic route of [ 22246-13-5 ]

[ 22246-13-5 ] Synthesis Path-Upstream 1~4

1
[ 22246-16-8 ]
[ 22246-13-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With ammonium chloride; zinc In methanol at 0 - 20℃; for 1 h;	To a solution of 6-nitro-3,4-dihydroquinolin-2(lH)-one (3 g) in MeOH (60 mL) at 0°C, Zn dust (5 eq) and ammonium chloride (5 eq) were added portion wise and the mixture stirred at rt for 1 h while monitoring by TLC. After completion, the mixture was filtered over Celite® bed and resulting filtrate concentrated. The residue was diluted with 5percent MeOH in DCM and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated to obtain 6-amino-3,4-dihydroquinolin-2(lH)-one (2.3 g, 91percent). 1H NMR (DMSO-d₆, 400 MHz): δ 9.654 (brs, 1H), 6.53 (d, 1H), 6.378-6.334 (m, 2H), 4.707 (brs, 2H), 2.699 (t, 2H), 2.330 (t, 2H).
63%	With hydrogen In methanol	To a suspension of l,2-dihydro-6-nitroisoquinolin-3(4H)-one (10.3 g, 53.6 mmol) in MeOH (150 mL) was added 10percent Pd/C (1.14 g, 1.07 mmol) and the mixture was stirred overnight under H₂ (1 atm). After filtration, the filtrate was concentrated and the residue was suspended in acetone, filtered and precipitated with cone. HCl (10 mL). The resulting precipitate was collected, washed with H₂O and acetone and recrystallized from MeOH/H₂O to yield 6-amino-l,2-dihydroisoquinolin-3(4H)-one as a grey solid (6.7 g, 63 percent yield).
1.8 g	With ammonium chloride; zinc In ethanol; water at 80℃; for 1 h;	6-Nitro-3,4- dihydroquinolin-2(lH)-one (1.0 g, 5.2 mmol) was dissolved in 40 mL of EtOH, and then H4CI (2.76 g, 52 mmol) in 20 mL of H2O and Zn dust (2.37 g, 36.4 mmol) were added. After refluxing at 80 °C for 1 h, the mixture was filtered to remove Zn dust. The filtration was concentrated to give the desired product (1.8 g, including partial H4CI) as a gray solid. NMR (300 MHz, DMSO-^e) δ 9.67 (s, 1H), 6.55 (d, J = 8.2 Hz, 1H), 6.42 - 6.31 (m, 2H), 2.70 (t, J= 7.5 Hz, 2H), 2.33 (dd, J= 8.5 Hz, 6.5 Hz, 2H).

Reference： [1] Patent: WO2015/38417, 2015, A1, . Location in patent: Page/Page column 90; 91
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4606 - 4609
[3] Patent: WO2006/71940, 2006, A2, . Location in patent: Page/Page column 416
[4] Proceedings of the Imperial Academy (Tokyo), 1939, vol. 15, p. 148,153[5] Chem. Zentralbl., 1939, vol. 110, # II, p. 3089
[6] Archiv der Pharmazie, 2008, vol. 341, # 12, p. 794 - 799
[7] European Journal of Medicinal Chemistry, 2014, vol. 73, p. 217 - 224
[8] Patent: WO2016/33100, 2016, A1, . Location in patent: Page/Page column 145
[9] European Journal of Medicinal Chemistry, 2018, vol. 151, p. 450 - 461
[10] Patent: WO2018/112037, 2018, A1, . Location in patent: Paragraph 0146

2
[ 553-03-7 ]
[ 22246-13-5 ]

Reference： [1] Proceedings of the Imperial Academy (Tokyo), 1939, vol. 15, p. 148,153[2] Chem. Zentralbl., 1939, vol. 110, # II, p. 3089
[3] European Journal of Medicinal Chemistry, 2014, vol. 73, p. 217 - 224
[4] Patent: WO2015/38417, 2015, A1,

3
[ 3460-04-6 ]
[ 22246-13-5 ]

Reference： [1] Patent: WO2015/38417, 2015, A1,

4
[ 62-53-3 ]
[ 22246-13-5 ]

Reference： [1] Patent: WO2015/38417, 2015, A1,

[ 22246-13-5 ] Synthesis Path-Downstream 1~20

1
[ 22246-16-8 ]
[ 22246-13-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 4h;	Into a lOO-mL round-bottomed flask was placed a mixture of 6-nitro-3,4-dihydroquinolin-2(lH)-one (1.92 g, 10.0 mmol, 1.00 equiv), methanol (50 mL) and Pd/C (200 mg). The reaction mixture was stirred under hydrogen atmosphere for 4 hours at room temperature until the starting material had disappeared, as shown by TLC analysis. The reaction mixture was filtered and the filtrate was concentrated. This resulted in 1.60 g (99%) of 6-amino-3,4-dihydroquinolin-2(lH)-one as a light green solid. LC-MS (ES) [M+l]+ m/z 163.1.
91%	With ammonium chloride; zinc; In methanol; at 0 - 20℃; for 1h;	To a solution of 6-nitro-3,4-dihydroquinolin-2(lH)-one (3 g) in MeOH (60 mL) at 0C, Zn dust (5 eq) and ammonium chloride (5 eq) were added portion wise and the mixture stirred at rt for 1 h while monitoring by TLC. After completion, the mixture was filtered over Celite bed and resulting filtrate concentrated. The residue was diluted with 5% MeOH in DCM and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated to obtain 6-amino-3,4-dihydroquinolin-2(lH)-one (2.3 g, 91%). 1H NMR (DMSO-d6, 400 MHz): delta 9.654 (brs, 1H), 6.53 (d, 1H), 6.378-6.334 (m, 2H), 4.707 (brs, 2H), 2.699 (t, 2H), 2.330 (t, 2H).
63%	With hydrogen;palladium 10% on activated carbon; In methanol; under 760.051 Torr;	To a suspension of l,2-dihydro-6-nitroisoquinolin-3(4H)-one (10.3 g, 53.6 mmol) in MeOH (150 mL) was added 10% Pd/C (1.14 g, 1.07 mmol) and the mixture was stirred overnight under H2 (1 atm). After filtration, the filtrate was concentrated and the residue was suspended in acetone, filtered and precipitated with cone. HCl (10 mL). The resulting precipitate was collected, washed with H2O and acetone and recrystallized from MeOH/H2O to yield 6-amino-l,2-dihydroisoquinolin-3(4H)-one as a grey solid (6.7 g, 63 % yield).

	With palladium on activated charcoal; hydrogen; for 8h;	Example 96: Preparation of 6-amino-3,4-dihydroquinolin-2(lH)-one6-Nitro-3,4-dihydroquinolin-2(lH)-one (2.53 g, 13.1 mmol, 1.0 equiv) and palladium on carbon (100 mg) were mixed in EtOH (40 mL). A balloon of hydrogen gas was applied for 8 h, then the mixture was filtered through Celite with DCM and concentrated in vacuo. The resultant brown solid (2.02 g) was used without further purification. This compound does not ionize well, thus there is no product MS peak. 1H MR (400 MHz, DMSO-d6) delta: 9.65 (s, 1 H), 6.54 (d, 1H, J = 8.4 Hz), 6.39 (d, 1H, J= 2.4 Hz), 6.35 (dd, 1H, J= 2.8, 8.4 Hz), 4.73 (bs, 2H), 2.70 (t, 2H, J = 8.0 Hz), 2.33 (t, 2H, J= 7.2 Hz).
	With ammonium chloride; zinc; In ethanol; water; at 80℃; for 1h;	6-Nitro-3,4-dihydroquinolin-2(1H)-one (1.0g, 5.2mmol) was dissolved in 40mL of EtOH, and then NH4Cl (2.76g, 52mmol) in 20mL of H2O and Zn dust (2.37g, 36.4mmol) were added. After refluxing at 80C for 1h, the mixture was filtered to remove Zn dust. The filtration was concentrated to give 25 (1.8g, including partial NH4Cl) as a gray solid. 1H NMR (300MHz, DMSO-d6) delta 9.67 (s, 1H), 6.55 (d, J=8.2Hz, 1H), 6.42-6.31 (m, 2H), 2.70 (t, J=7.5Hz, 2H), 2.33 (dd, J=8.5Hz, 6.5Hz, 2H).
1.8 g	With ammonium chloride; zinc; In ethanol; water; at 80℃; for 1h;	6-Nitro-3,4- dihydroquinolin-2(lH)-one (1.0 g, 5.2 mmol) was dissolved in 40 mL of EtOH, and then H4CI (2.76 g, 52 mmol) in 20 mL of H2O and Zn dust (2.37 g, 36.4 mmol) were added. After refluxing at 80 C for 1 h, the mixture was filtered to remove Zn dust. The filtration was concentrated to give the desired product (1.8 g, including partial H4CI) as a gray solid. NMR (300 MHz, DMSO-^e) delta 9.67 (s, 1H), 6.55 (d, J = 8.2 Hz, 1H), 6.42 - 6.31 (m, 2H), 2.70 (t, J= 7.5 Hz, 2H), 2.33 (dd, J= 8.5 Hz, 6.5 Hz, 2H).
	With hydrogenchloride; iron; In ethanol; water; for 2.5h;Reflux;	15.1 g of compound II and 30.4 Ml of H2SO4 (78%) were placed in a 250 mL reaction flask, stirred, and cooled to 0 to 5 C with an ice salt bath, and 31.5 mL of H 2 SO 4 (78%) and 9.2 mL (01186 mol) of HNO 3 (65) were added dropwise. %) of the mixture, control the drop accelerationDegree, keep the reaction temperature below 10 C, remove the ice bath after the addition is completed, continue to react for 3h, pour the reaction solution into ice water, let it stand, filter it by suction, wash it twice with water, dry the filter cake, and use acetone Crystallization gave 17.6 g of pale yellow solid product <strong>[22246-16-8]6-nitro-3,4-dihydro-2(1H)quinolinone</strong> (III) in a yield of 8912%; mp 203-204 C; The peak of 192 is consistent with the mass of the product, and the peaks of each fragment are also consistent;First, 7.63 g of reduced iron powder and 2.75 mL of concentrated hydrochloric acid (36%) were added to the reaction flask, stirred and 150 mL of ethanol (95%) was added, and then the temperature was raised to reflux. After cooling, 7.9 g of the compound was added in portions.III, reheating to reflux, after 2.5h reaction, stop the reaction, heat filtration, and rinse the iron mud in the bottle with hot ethanol for 2 to 3 times, concentrate the filtrate, add a small amount of water, and put it in the refrigerator to cool, a large amount of solids are precipitated. Then, suction filtration, the obtained filter cake was dried to obtain 618 g of pale yellow crystal 6-amino-3,4-dihydro-2(1H)quinolinone (IV), yield 9916%, mp 174-175 C;Dissolve 1.4 g of sodium nitrite in 3.71 mL of water; then pour 4.3 mL of concentrated sulfuric acid (98%) and 617 mL of water into the reaction flask, add 2.95 of the starting compound IV with stirring, stir until it is a paste, and cool with an ice salt bath until 0 to 5 C, add a pre-formed aqueous solution of sodium nitrite, control the dropAcceleration, so that the reaction temperature does not exceed 10 C; after the addition is completed, the ice bath is removed, heated to reflux with a preheated oil bath, the reaction is stopped for 40 min, the reaction is stopped, 10 mL of water is added, cooled, suction filtered, dried to give 216 g shallow Yellow solid 1, yield 86.7%;

Reference： [1]Patent: WO2020/28461,2020,A1 .Location in patent: Paragraph 00177-
[2]Patent: WO2015/38417,2015,A1 .Location in patent: Page/Page column 90; 91
[3]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 4606 - 4609
[4]Patent: WO2006/71940,2006,A2 .Location in patent: Page/Page column 416
[5]Proceedings of the Imperial Academy (Tokyo),1939,vol. 15,p. 148,153
Chemisches Zentralblatt,1939,vol. 110,p. 3089
[6]Archiv der Pharmazie,2008,vol. 341,p. 794 - 799
[7]European Journal of Medicinal Chemistry,2014,vol. 73,p. 217 - 224
[8]Patent: WO2016/33100,2016,A1 .Location in patent: Page/Page column 145
[9]European Journal of Medicinal Chemistry,2018,vol. 151,p. 450 - 461
[10]Patent: WO2018/112037,2018,A1 .Location in patent: Paragraph 0146
[11]Patent: CN109810054,2019,A .Location in patent: Paragraph 0009; 0010

2
[ 22246-13-5 ]
[ 43204-63-3 ]
[ 86813-31-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In methanol;	EXAMPLE 1 A mixture of 9.36 g of 6-amino-3,4-dihydrocarbostyril, 18 g of bis(beta-bromoethyl)amine monohydrobromide and 70 ml of methanol was refluxed for 15 hours while stirring. After cooling, 3.06 g of sodium carbonate was added and the resulting mixture was refluxed for 8 hours while stirring. The reaction mixture was cooled to precipitate crystals which then were collected by filtration, the crystals were washed with methanol to give 9.1 g of 6-(1-piperazinyl)-3,4-dihydrocarbostyril hydrobromide, m.p. 289-293 C. (decomp.) (methanol-water), colorless needles.

Reference： [1]Chemical and Pharmaceutical Bulletin,1984,vol. 32,p. 2100 - 2110
[2]Patent: US4415572,1983,A

3
[ CAS Unavailable ]
[ 81839-45-4 ]
[ 22246-13-5 ]
[ 81840-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphoric acid In water	131 EXAMPLE 131 EXAMPLE 131 A mixture of 2.7 g of 6-amino-3,4-dihydrocarbostyril, 5.9 g of N,N-bis(2-hydroxyethyl)-3,4-dimethoxybenzamide and 8.6 g of 85% phosphoric acid was reacted at 165° to 175° C. for 4.5 hours while stirring. After allowing to cool, to the reaction mixture was added dropwise about 50 ml of water to dissolve. The solution was neutralized with an aqueous 48% sodium hydroxide solution and extracted with chloroform. After drying the extract over potassium carbonate, chloroform was distilled off. Recrystallization of the residue from ethanol-chloroform gave 4.7 g of 6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 238°-239.5° C., colorless granules.

Reference： [1]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - US4415572, 1983, A

4
[ 22246-13-5 ]
[ 189278-27-1 ]
[ 1579950-36-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 566 - 571

5
[ 22246-13-5 ]
[ 175205-81-9 ]
[ 1579950-38-1 ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 566 - 571

6
[ 22246-13-5 ]
[ 436799-33-6 ]
[ 1579950-40-5 ]

Reference： [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 566 - 571

7
[ 22246-13-5 ]
[ 3972-64-3 ]
[ 1611467-11-8 ]

Yield	Reaction Conditions	Operation in experiment
42%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In toluene; at 100℃; for 9h;Inert atmosphere;	General procedure: Toluene (4.5mL) was added to a flask containing 6-bromo-3,4-dihydroquinolin-2(1H)-one (300mg, 1.33mmol), 3-(trifluoromethoxy)aniline (231muL, 1.73mmol), Pd2(dba)3 (15.2mg, 0.02mmol), 2-dicyclohexylphosphino-2?,4?,6?-triisopropylbiphenyl (31.6mg, 0.07mmol) and NaOt-Bu (192mg, 2.00mmol) under an argon atmosphere. The mixture was stirred at 100°C for 9h. After cooling, the reaction mixture was diluted with EtOAc, and filtered through a pad of Celite. The filtrate was concentrated in vacuo. Crude material was purified by flash chromatography with n-hexane/EtOAc (2:3) to afford the desired diaryl amine 11i

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3171 - 3179

8
[ 3460-04-6 ]
[ 22246-13-5 ]

Reference： [1]Patent: WO2015/38417,2015,A1
[2]Patent: CN109810054,2019,A

9
[ 22246-13-5 ]
[ 22236-04-0 ]
[ 3932-97-6 ]
6-((4-((2-(difluoromethoxy)phenyl)amino)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3,4-dihydroquinolin-2(1H)-one [ No CAS ]
N<SUP>2</SUP>,N<SUP>4</SUP>-bis(2-(difluoromethoxy)phenyl)-5-(trifluoromethyl)pyrimidine-2,4-diamine [ No CAS ]
6,6'-((5-(trifluoromethyl)pyrimidine-2,4-diyl)bis(azanediyl))bis(3,4-dihydroquinolin-2(1H)-one) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 27 mg 2: 9 mg 3: 14 mg	Stage #1: 2-(difluoromethoxy)aniline; 2,4-dichloro-5-trifluoromethylpyrimidine With N-ethyl-N,N-diisopropylamine In acetonitrile at 100℃; for 0.166667h; Microwave irradiation; Stage #2: 6-amino-3,4-dihydro-1H-quinolin-2-one With acetic acid at 120℃; for 0.166667h; Microwave irradiation;	120 Example 99: Preparation of N-meth l-2- 2-(phenylamino)-5-(trifluoromethyl)pyrimidin-4-yI)oxy)benzamide General procedure: Example 99: Preparation of N-meth l-2- 2-(phenylamino)-5-(trifluoromethyl)pyrimidin-4-yI)oxy)benzamideA solution of 2,4-dichloro-5-(trifluoromethyl)pyrimidine (100 mg, 0.461 mmol, 1 .0 equiv), 2-hydroxy-N-methylbenzamide (69 mg, 0.461 mmol, 1.0 equiv) and N,N-diisopropyl ethylamine (0.08 mL, 0.461 mmol, 1.0 equiv) in acetonitrile (3 mL) was microwaved at 100 °C for 10 min. The mixture was concentrated in vacuo, then aniline (0.042 mL, 0.461 mmol, 1.0 equiv) and acetic acid (2 mL) were added. This mixture was microwaved at 120 °C for 10 min, then concentrated in vacuo. A fraction of the crude product was purified by reverse phase HPLC to yield the product (13 mg). MS calcd for [C19Hi5F3N402+H]+: 389.12, found 389.32.

Reference： [1]Current Patent Assignee: SALK INSTITUTE FOR BIOLOGICAL STUDIES; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; YALE UNIVERSITY - WO2016/33100, 2016, A1 Location in patent: Page/Page column 153; 154

10
[ 22246-13-5 ]
[ 3177-24-0 ]
[ 765-30-0 ]
4-(cyclopropylamino)-2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)amino)pyrimidine-5-carbonitrile [ No CAS ]
2-(cyclopropylamino)-4-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)amino)pyrimidine-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14 mg; 14 mg		Example 287: Preparation of 4-(cyclopropylamino)-2-((2-oxo-l,2,3,4-tetrahydroquinolin-6- yl)amino)pyrimidine-5-carbonitrile and 2-(cyclopropylamino)-4-((2-oxo-l,2,3>4- tetrahydroquinolin-6-yl)amino)pyrimidine-5-carbonitrile.2,4-Dichloropyrimidine-5-carbonitrile (0.100 g, 0.575 mmol), cyclopropanamine (0.040 ml, 0.575 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.1 10 ml, 0.632 mmol) were mixed in acetonitrile (2 ml). The mixture was microwaved at 70 °C for 10 min and then concentrated. 6- amino-3,4-dihydroquinolin-2(l H)-one (0.093 g, 0.575 mmol) and acetic acid (0.035 g, 0.575 mmol) were added. The mixture was microwaved at 1 10 °C for 20 min and then concentrated. 14 mg of 4-(cyclopropylamino)-2-((2-oxo- l ,2,3,4-tetrahydroquinolin-6-yl)amino)pyrimidine-5- carbonitrile and 14 mg of 2-(cyclopropylamino)-4-((2-oxo-l ,2,3,4-tetrahydroquinolin-6- yl)amino)pyrimidine-5-carbonitrile were recovered after automated reverse phasechromatography (water-MeCN). MS calcd for [Ci7Hi6N60+H]+: 321.15 found 321.00.

Reference： [1]Patent: WO2016/33100,2016,A1 .Location in patent: Page/Page column 223

11
[ 22246-13-5 ]
[ 524033-55-4 ]
6-((4-(cyclopropylamino)quinazolin-2-yl)amino)-3,4-dihydroquinolin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80 mg	With acetic acid at 110℃; for 0.166667h; Microwave irradiation;	263 Example 263: Preparation of 6-((4-(cyclopropylamino)quinazolin-2-yl)amino)-3,4- dihydroquinoli -2(lH)-one Example 263: Preparation of 6-((4-(cyclopropylamino)quinazolin-2-yl)amino)-3,4- dihydroquinoli -2(lH)-one2-Chloro-N-cyclopropylquinazolin-4-amine (0.055 g, 0.250 mmol) and 6-amino-3,4- dihydroquinolin-2(lH)-one (0.041 g, 0.250 mmol) were mixed in acetic acid ( 1 ml). The mixture was microwaved at 1 10 °C for 10 min and then concentrated. Added acetone and filtered the solid to give 80 mg of product. MS calcd for [C20Hi9N5O+H]+: 346.17 found 346.30.

Reference： [1]Current Patent Assignee: YALE UNIVERSITY; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; SALK INSTITUTE FOR BIOLOGICAL STUDIES - WO2016/33100, 2016, A1 Location in patent: Page/Page column 214

12
[ 22246-13-5 ]
[ 1192711-37-7 ]
4-(cyclopropylamino)-2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)amino)pyrimidine-5-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74 mg	With acetic acid; at 120.0℃; for 0.333333h;Microwave irradiation;	Example 286: Preparation of 4-(cyclopropyIamino)-2-((2-oxo-l,2,3,4-tetrahydroquinolin-6- yI)amino)pyrimidine-5-carboxylic acid2-Chloro-4-(cyclopropylamino)pyrimidine-5-carboxylic acid (0.100 g, 0.468 mmol) and 6-amino-3,4-dihydroquinolin-2(lH)-one (0.076 g, 0.468 mmol) were mixed in acetic acid (1 ml). The mixture was microwaved at 120 C for 20 min and then concentrated. Added acetone and filtered the solid. Added MeOH to the previous solid and filtered to give 74 mg of final product. MS calcd for [C17H17N503+H]+: 340.14 found 340.00.

Reference： [1]Patent: WO2016/33100,2016,A1 .Location in patent: Page/Page column 222; 223

13
[ 845305-87-5 ]
[ 22246-13-5 ]
C₁₆H₁₆N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃;	To a solution of <strong>[845305-87-5]5-bromo-N-methylpicolinamide</strong> (80mg, 0.37mmol) and 6-amino-3,4-dihydroquinolin-2(1H)-one (50mg, 0.31mmol) in 5mL 1,4-dioxane, Pd(OAc)2 (18g, 0.08mmol), Cs2CO3 (202mg, 0.62mmol) and xantphos (90mg, 0.16mmol) were added. The mixture was allowed to reflux at 110C overnight. Then the mixture was filtered, poured into H2O and extracted by DCM. The organic layer was washed with saturated NaHCO3 (aq.), brine and dried over anhydrous Na2SO4. The resulting solution was evaporated, and the residue was purified by silica gel column (DCM/MeOH=50:1) to give the desired product (58mg, 63%) as a white solid. m. p.: 276-278C (decomposition). 1H NMR (300MHz, DMSO-d6) δ 10.02 (s, 1H), 8.58 (d, J=2.5Hz, 1H), 8.37 (s, 1H), 8.19 (s, 1H), 7.86-7.74 (m, 1H), 7.44-7.32 (m, 1H), 6.99 (d, J=9.0Hz, 2H), 6.84 (d, J=3.6Hz, 1H), 2.85 (s, 2H), 2.78 (s, 3H), 2.44 (s, 2H). 13C NMR (75MHz, DMSO-d6) δ 170.31, 165.02, 144.05, 140.36, 135.99, 135.56, 134.07, 125.25, 123.17, 120.24, 119.83, 119.50, 116.31, 30.81, 26.25, 25.43. HRMS (ESI) m/z calcd for C16H17N4O2 [M+H]+, 297.1352; found, 297.1345.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 151,p. 450 - 461

14
[ 22246-13-5 ]
[ 22952-32-5 ]
5-chloro-2-methoxy-N-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)benzene sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 1h;	To a solution of ZL0349 (70 mg, 0.43 mmol) and Et3N (87 mg, 0.86 mmol) in 5 mL DMF, <strong>[22952-32-5]5-chloro-2-methoxybenzenesulfonyl chloride</strong> (156 mg, 0.65 mmol) was added. After stirring at rt for 1 h, the mixture was poured into 20 mL ice- water. The precipitate was filtered to get the desired product (45 mg, 29%) as a white solid. HPLC purity 98.9 % (fe = 16.18 min). 1H MR (300 MHz, DMSO-^e) delta 9.97 (s, 1H), 9.85 (s, 1H), 7.61 (s, 1H), 7.24 (dd, J = 10.2, 6.8 Hz, 2H), 6.94 - 6.79 (m, 2H), 6.67 (d, J = 8.4 Hz, 1H), 3.91 (s, 3H), 2.81 - 2.71 (m, 2H), 2.36 (t, J = 7.5 Hz, 2H). 13C MR (75 MHz, DMSO- d6) S 170.38, 155.70, 135.72, 134.90, 133.70, 131.74, 129.59, 128.53, 127.45, 124.68, 124.05, 121.63, 120.67, 115.80, 115.36, 57.00, 30.58, 25.25. ESI-MS (M + H)+ m/z 367.1. HR ESI- MS (M + H)+ m/z = 367.0506 (calcd for Ci6Hi6N2O4SCl:367.0519).
45 mg	With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 1h;	To a solution of 25 (70mg, 0.43mmol) and Et3N (87mg, 0.86mmol) in 5mL DMF, <strong>[22952-32-5]5-chloro-2-methoxybenzenesulfonyl chloride</strong> (156mg, 0.65mmol) was added. After stirring at rt. for 1h, the mixture was poured into 20mL of ice-water. The precipitate was filtered to get the desired product (45mg, 29%) as a white solid. m. p.: 253-255C (decomposition). 1H NMR (300MHz, DMSO-d6) delta 9.97 (s, 1H), 9.85 (s, 1H), 7.61 (s, 1H), 7.24 (dd, J=10.2, 6.8Hz, 2H), 6.94-6.79 (m, 2H), 6.67 (d, J=8.4Hz, 1H), 3.91 (s, 3H), 2.81-2.71 (m, 2H), 2.36 (t, J=7.5Hz, 2H). 13C NMR (75MHz, DMSO-d6) delta 170.38, 155.70, 135.72, 134.90, 133.70, 131.74, 129.59, 128.53, 127.45, 124.68, 124.05, 121.63, 120.67, 115.80, 115.36, 57.00, 30.58, 25.25. HRMS (ESI) m/z calcd for C16H16N2O4SCl [M+H]+, 367.0519; found, 367.0506.

Reference： [1]Patent: WO2018/112037,2018,A1 .Location in patent: Paragraph 0148
[2]European Journal of Medicinal Chemistry,2018,vol. 151,p. 450 - 461

15
[ 22246-13-5 ]
[ 475216-25-2 ]
N-methyl-3-nitro-4-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)amino)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 80℃; for 72h;	To a stirred solution of <strong>[475216-25-2]4-fluoro-N-methyl-3-nitrobenzamide</strong>2 (500 mg) in N-methyl-2- pyrrolidinone (5 ml) were added 6-amino-3,4-dihydroquinolin-2(iH)-one24 (450 mg) and N,Ndiisopropylethylamine (489 mg). The reaction mixture was heated at 80 C for 3 days. LC-MS analysis indicated that the reaction was incomplete. The reaction mixture was heated at 120 Cfor 1 day. The reaction mixture was cooled to room temperature and ethyl acetate (10 ml) and water (3 ml) were added. An orange precipitate formed. The precipitate was collected by filtration, washed with ethyl acetate, and dried in vacuo to give N-methyl-3-nitro-4-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)amino)benzamide as an orange solid (825 mg, 96 %). MS (ISP):341.0 ([M+H]j.

Reference： [1]Patent: WO2019/43208,2019,A1 .Location in patent: Page/Page column 57; 58

16
[ 22246-13-5 ]
[ 54197-66-9 ]

Yield	Reaction Conditions	Operation in experiment
216 g	With sulfuric acid; sodium nitrite; In water; at 0 - 10℃; for 0.666667h;	15.1 g of compound II and 30.4 Ml of H2SO4 (78%) were placed in a 250 mL reaction flask, stirred, and cooled to 0 to 5 C with an ice salt bath, and 31.5 mL of H 2 SO 4 (78%) and 9.2 mL (01186 mol) of HNO 3 (65) were added dropwise. %) of the mixture, control the drop accelerationDegree, keep the reaction temperature below 10 C, remove the ice bath after the addition is completed, continue to react for 3h, pour the reaction solution into ice water, let it stand, filter it by suction, wash it twice with water, dry the filter cake, and use acetone Crystallization gave 17.6 g of pale yellow solid product 6-nitro-3,4-dihydro-2(1H)quinolinone (III) in a yield of 8912%; mp 203-204 C; The peak of 192 is consistent with the mass of the product, and the peaks of each fragment are also consistent;First, 7.63 g of reduced iron powder and 2.75 mL of concentrated hydrochloric acid (36%) were added to the reaction flask, stirred and 150 mL of ethanol (95%) was added, and then the temperature was raised to reflux. After cooling, 7.9 g of the compound was added in portions.III, reheating to reflux, after 2.5h reaction, stop the reaction, heat filtration, and rinse the iron mud in the bottle with hot ethanol for 2 to 3 times, concentrate the filtrate, add a small amount of water, and put it in the refrigerator to cool, a large amount of solids are precipitated. Then, suction filtration, the obtained filter cake was dried to obtain 618 g of pale yellow crystal 6-amino-3,4-dihydro-2(1H)quinolinone (IV), yield 9916%, mp 174-175 C; The mass spectrum obtained by mass spectrometry has a peak of 162 which is consistent with the mass of the product, and the peaks of the fragments are also consistent;Dissolve 1.4 g of sodium nitrite in 3.71 mL of water; then pour 4.3 mL of concentrated sulfuric acid (98%) and 617 mL of water into the reaction flask, add 2.95 of the starting compound IV with stirring, stir until it is a paste, and cool with an ice salt bath until 0 to 5 C, add a pre-formed aqueous solution of sodium nitrite, control the dropAcceleration, so that the reaction temperature does not exceed 10 C; after the addition is completed, the ice bath is removed, heated to reflux with a preheated oil bath, the reaction is stopped for 40 min, the reaction is stopped, 10 mL of water is added, cooled, suction filtered, dried to give 216 g shallow Yellow solid 1, yield 86.7

Reference： [1]Patent: CN109810054,2019,A .Location in patent: Paragraph 0009; 0010

17
[ 5617-70-9 ]
[ 22246-13-5 ]
2-oxo-1-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)pyrrolidine-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In N,N-dimethyl-formamide; acetonitrile at 60 - 70℃; for 12h;

Reference： [1]Heinrich, Timo; Seenisamy, Jeyaprakashnarayanan; Becker, Frank; Blume, Beatrix; Bomke, Jörg; Dietz, Melanie; Eckert, Uwe; Friese-Hamim, Manja; Gunera, Jakub; Hansen, Kerrin; Leuthner, Birgitta; Musil, Djordje; Pfalzgraf, Jens; Rohdich, Felix; Siegl, Christian; Spuck, Dieter; Wegener, Ansgar; Zenke, Frank T. [Journal of Medicinal Chemistry, 2019, vol. 62, # 24, p. 11119 - 11134]

18
[ 4080-54-0 ]
[ 22246-13-5 ]
3-ethyl-N-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h;	Into a 40- mL vial was placed a mixture of 6-amino-7-fluoro-3,4-dihydroquinolin-2(lH)-one (180 mg, 1.00 mmol, 1.00 equiv), N,N-dimethylformamide (5 mL), <strong>[4080-54-0]3-ethylisonicotinic acid</strong> (166 mg, 1.10 mmol, 1.10 equiv), N-ethyl-N-isopropylpropan-2-amine (387 mg, 3.00 mmol, 3.00 equiv) and l-((dimethylamino)(dimethyliminio)methyl)-lH-[l,2,3]triazolo[4,5-b]pyridine 3- oxide hexafluorophosphate(V) (570 mg, 1.50 mmol, 1.50 equiv). The reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was filtered and the filtrate was purified by prep-HPLC. This resulted in 260 mg (88%) of 3-ethyl-N-(2-oxo-l,2,3,4- tetrahydroquinolin-6-yl)isonicotinamide. LC-MS (ES) [M+l]+ m/z: 296.1. Tl NMR (DMSO-i, 300 MHz) was consistent with a compound having the structure of 3-ethyl-N-(2- oxo-l,2,3,4-tetrahydroquinolin-6-yl)isonicotinamide.

Reference： [1]Patent: WO2020/28461,2020,A1 .Location in patent: Paragraph 00184

19
[ 22246-13-5 ]
[ 78060-54-5 ]
2-[(2-oxo-3,4-dihydro-1H-quinolin-6-yl)amino]quinoline-6-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19 mg	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃; for 10h; Inert atmosphere;	36.3 To a solution of 2-chloroquinolme-6-carbonitrile (200 mg, 1.06 mmol, 1 eq) and 6-amino-3,4-dihydro-1H-quinolin-2-one (171.98 mg, 1.06 mmol, 1 eq) in dioxane (5 mL) was added Pd(OAc)2 (47.61 mg, 212.07 umol, 0.2 eq), Cs2CO3 (690.98 mg, 2.12 mmol, 2 eq) and Xantphos (122.71 mg, 212.07 umol, 0.2 eq). The mixture was stirred at 80 °C for 10 hr under N2. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give a residue. The residue was purified by prep-HPLC (column: Waters Abridge Prep OBD C18 15040mm10um;mobile phase: [water(0.05%NH3H2O+10mM NH4HCO3)-ACN];B%: 35%-65%,8min) to give 2-[(2-oxo-3,4-dihydro-1H-quinolin-6- yl)amino]quinoline-6-carbonitrile (88,19 mg, 99% purity), LCMS: (M+H)+ : 315.1, and 2- [[1-(6-cyano-2-quinolyl)-2-oxo-3,4-dihydroquinolin-6-y.]amino]quinoline~6-carbonitrile (20 mg, 98% purity), LCMS: (M+H)+ : 467.2.

Reference： [1]Current Patent Assignee: KAYOTHERA; PRINCETON UNIVERSITY - WO2021/151062, 2021, A1 Location in patent: Paragraph 0334

20
[ 4295-12-9 ]
[ 22246-13-5 ]
6-[(7-methyl-2-quinolyl)amino]-3,4-dihydro-1H-quinolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33 mg	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 12h;	39 Example 39, Synthesis of Compound 91 [0340] To the mixture of 2-chloro-7-methyl-quinoline (90 mg, 506.67 umol, 1 eq) and 6- amino-3,4-dihydro-1H-quinolin-2-one (82.18 mg, 506,67 umol, 1 eq) in 1,4-dioxane (10 inL) was added Pd(OAc)2 (22.75 mg, 101.33 umol, 0,2 eq), (5-diphenylphosphanyl-9,9- dimethyl-xanthen-4-yl)-diphenyl-phosphane (58.63 mg, 101.33 umol, 0,2 eq) and Cs2CO3 (330.17 mg, 1.01 mmol, 2 eq). The mixture was stirred at 110°C for 12 hr, The mixture was cooled to 25 °C. The mixture was filtered. The filtrate was concentrated in vacuum to get the residue. The residue was purified by prep-TLC (SiO2, Petroleum ether: Ethyl acetate = 0: 1). 6-[(7-methyl-2-quinolyl)amino]-3,4-dihydro-1H-quinolin-2-one (33 mg, 98% purity) was obtained. LCMS: (M+H)+ : 304.1.

Reference： [1]Current Patent Assignee: KAYOTHERA; PRINCETON UNIVERSITY - WO2021/151062, 2021, A1 Location in patent: Paragraph 0340

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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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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. 22246-13-5 ] {[proInfo.proName]}

Quality Control of [ 22246-13-5 ]

Related Doc. of [ 22246-13-5 ]

Product Details of [ 22246-13-5 ]

Calculated chemistry of [ 22246-13-5 ]

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Druglikeness

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Application In Synthesis of [ 22246-13-5 ]

[ 22246-13-5 ] Synthesis Path-Upstream 1~4

[ 22246-13-5 ] Synthesis Path-Downstream 1~20

Related Functional Groups of [ 22246-13-5 ]

Amides

Amines

Related Parent Nucleus of [ 22246-13-5 ]

Tetrahydroquinolines

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[ 22246-13-5 ]

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[ 22246-13-5 ]