62484-29-1|2,4,8-Trichloroquinazoline| Ambeed

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Quality Control of [ 62484-29-1 ] Purity: 95% SDS Specification

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Product Details of [ 62484-29-1 ]

CAS No. :	62484-29-1
Formula :	C₈H₃Cl₃N₂
M.W :	233.48
SMILES Code :	ClC1=CC=CC2=C1N=C(Cl)N=C2Cl
MDL No. :	MFCD09954870
InChI Key :	XSZZHOALJUVOIG-UHFFFAOYSA-N
Pubchem ID :	21473996

Safety of [ 62484-29-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 62484-29-1 ]

* 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 [ 62484-29-1 ]

[ 62484-29-1 ] Synthesis Path-Downstream 1~35

2
[ 62484-22-4 ]
[ 62484-29-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With trichlorophosphate; for 16h;Reflux;	(1041) To the compound 77 (3.8 g, 19.33 mmol), 60 mL POCl3 was added. The mixture was then heated at reflux for 16 hours. Excess POCl3 was removed in vacuum, and the residue was purified by column chromatography to provide 78 (3.11 g, 76%). Mass spectrum (ESI+): m/z=233 [M+1].
2.26 g (53%)	In ice-water; trichlorophosphate;	b) 3.6 g (0.01 8 mol) of 8-chloro-1,2,3,4-tetrahydroquinazoline-2,4-dione were suspended in 16.8 ml (0.18 mol) of phosphorus oxychloride and boiled under reflux for 17 hrs. The reaction mixture was left to cool to room temperature and poured on to ice-water. The brown precipitate was extracted with dichloromethane, chromatographed over silica gel with dichloromethane as the eluent and recrystallized from diisopropyl ether. Yield: 2.26 g (53%) of 2,4,8-trichloro-quinazoline as yellow crystals; m.p. 155-156 C.
	With N,N-dimethyl-aniline; trichlorophosphate; at 115℃; for 4h;	Second Step: Step 2-2 of Scheme 2 A mixture of the product (VI)-B (700 mg, 3.56 mmol) of the first step, N,N-dimethylaniline (0.1 mL) and POCl3 (7 mL) was stirred at 115C for 4 hours. After cooling to room temperature, the reaction mixture was added to ice water (20 mL). The precipitated solid was collected by filtration, washed with water and then dried to obtain 414 mg of 2,4,8-trichloroquinazoline (VII)-B, which is a kind of the compound (VII) in Scheme 2. [Show Image] 1H-NMR (CD3OD) d (ppm): 8.31 (d, 1H, J = 8.1 Hz) 8.21 (d, 1H, J = 8.7 Hz), 7.78 (t, 1H, J = 8.1 Hz).

References: [1]Patent: US2016/168140,2016,A1 .Location in patent: Paragraph 1041.
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 2297 - 2300.
[3]Patent: US5688803,1997,A .
[4]Patent: EP2226315,2010,A1 .Location in patent: Page/Page column 33.
[5]Journal of Medicinal Chemistry,2014,vol. 57,p. 5141 - 5156.

3
[ 62484-29-1 ]
[ 62484-39-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere;	(1042) A mixture of 45 mL of 1N NaOH, 100 mL of THF, and 3.11 g of 78 was stirred at room temperature under N2 for 2 h. The solution was acidified with to PH 5. Then reaction mixture was diluted with water and ethyl acetate. Organic layer was separated, dried and evaporated. 79 was carried to the next step in the form of crude residue. Mass spectrum (ESI+): m/z=215 [M+1].

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2297 - 2300.
[2]Patent: US2016/168140,2016,A1 .Location in patent: Paragraph 1042.

4
[ 62484-29-1 ]
[ 769158-11-4 ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2297 - 2300.

5
[ 62484-29-1 ]
2-((2-(3-aminopiperidin-1-yl)-8-chloro-4-oxoquinazolin-3(4H)-yl)methyl)benzonitrile [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2297 - 2300.

6
[ 62484-29-1 ]
ethyl 2,8-dichloro-quinazoline-4-yl-carbazate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.56 g (54%)	In ice-water; dimethyl sulfoxide;	c) 1.5 g (0.014 mol) of ethyl carbazate were added to a solution of 2.26 g (0.009 mol) of <strong>[62484-29-1]2,4,8-trichloro-quinazoline</strong> in 95 ml of dimethyl sulphoxide. The reaction mixture was stirred at 70 C. for 2 hrs. and then poured on to ice-water. The yellow precipitate was filtered off, dried and recrystallized from methanol. Yield: 1.56 g (54%) of ethyl 2,8-dichloro-quinazoline-4-yl-carbazate as white crystals; m.p. 213-215 C.

References: [1]Patent: US5688803,1997,A .

7
[ 62484-29-1 ]
[ 1107694-84-7 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In tetrahydrofuran; water; at 20.0℃;	Third Step: Step 3-1 of Scheme 3 A THF solution (2 mL) of the product (VII)-B (151 mg, 0.65 mmol) of the second step and 28% ammonia water (1.5 mL) was stirred at room temperature overnight. The solvent was concentrated under reduced pressure and water (5 mL) was added to the resulting residue. The precipitated solid was collected by filtration, washed with water and then dried to obtain 122 mg of 2,8-dichloroquinazoline-4-amine (VIII)-B, which is a kind of the compound (VIII) in Scheme 3.[Chemical Formula 50] [Show Image] 1H-NMR (CD3OD) d (ppm): 8.05 (d, 1H, J = 8.4 Hz), 7.90(d, 1H, J = 7.5 Hz), 7.44 (t, 1H, J = 8.0 Hz).

References: [1]Patent: EP2226315,2010,A1 .Location in patent: Page/Page column 33.

8
[ 32315-10-9 ]
[ 53312-77-9 ]
[ 62484-29-1 ]

References: [1]Heterocycles,2012,vol. 85,p. 1417 - 1426.

9
[ 6388-47-2 ]
[ 62484-29-1 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 5141 - 5156.
[2]Patent: WO2014/101120,2014,A1 .
[3]Patent: WO2014/101373,2014,A1 .
[4]Patent: US2016/168140,2016,A1 .
[5]RSC Advances,2017,vol. 7,p. 22360 - 22368.

10
[ 62484-29-1 ]
[ 1589476-58-3 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 5141 - 5156.

11
[ 617-89-0 ]
[ 62484-29-1 ]
[ 1589476-83-4 ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 5141 - 5156.

12
[ 134784-37-5 ]
[ 62484-29-1 ]
[ 1616707-99-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 40℃; for 2h;	Step D: N'-(2,8-dichloroquinazolin-4-yl)-3.3-dimethoxypropanehvdrazide [0146] The mixture of <strong>[62484-29-1]2,4,8-trichloroquinazoline</strong> (step C, 4.0 g, 17.2 mmol), DIPEA (15 mL, 86.1 mmol) and 3,3-dimethoxypropanehydrazide (step A, 3.1 g, 20.7 mmol) in 1 ,4- dioxane (50 mL) was stirred at 40 C for 2 hours, and then concentrated. The residue was partitioned between DCM (50 mL) and aqueous NaHC03 (50 mL). The organic layer was washed with water and concentrated to get the title compound as a yellow solid which was characterized by LC/MS. LC-MS: m z (M+l) = 345.
	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 40℃; for 2h;	The mixture of <strong>[62484-29-1]2,4,8-trichloroquinazoline</strong> (step C, 4.0 g, 17.2 mmol), DIPEA (15 mL, 86.1 mmol) and 3,3-dimethoxypropanehydrazide (step A, 3.1 g, 20.7 rnrnol) in 1,4-dioxane (50 mL) was stirred at 40C for 2 hours, and then concentrated. The residue was partitioned between DCM (50 rnL) and aqueous NaHCO3 (50 mL). The organic layer was washed with water and concentrated to get the title compound as a yellow solid which was characterized by LC/MS. LC-MS: m/z (M+l) = 345.
	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 40℃; for 2h;	The mixture of <strong>[62484-29-1]2,4,8-trichloroquinazoline</strong> (step C, 4.0 g, 17.2 mmol), DIPEA (15 mL, 86.1 mmol) and 3,3-dimethoxypropanehydrazide (step A, 3.1 g, 20.7 mmol) in 1,4-dioxane (50 mL) was stirred at 40C for 2 hours, and then concentrated. The residue was partitioned between DCM (50 mL) and aqueous NaHC( (50 mL). The organic layer was washed with water and concentrated to get the title compound as a yellow solid which was characterized by LC/MS. LC-MS: m/z (M+l) = 345.

References: [1]Patent: WO2014/101120,2014,A1 .Location in patent: Paragraph 0146.
[2]Patent: WO2014/105666,2014,A1 .Location in patent: Paragraph 0143.
[3]Patent: WO2014/101373,2014,A1 .Location in patent: Page/Page column 66.

13
[ 62484-22-4 ]
[ 62484-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N-dimethyl-aniline; trichlorophosphate; at 140℃; for 16h;	Step C: 2A8-trichloroquinazoline [0145] 8-Chloroquinazoline-2,4-diol (step B, 15 g, 75.8 mmol) was added to POCl3 (70 mL, 763 mmol, 10 equiv.) in small portions. Dimethylaniline (3.7 g, 30.5 mmol, 0.4 equiv.) was added. The reaction mixture was stirred in 140 C for 16 hours. The mixture was cooled to room temperature, and added drop wise to ice-water (500 mL). The precipitate was collected and washed with ice-water. The solid was dissolved in DCM (500 mL), dried over MgS04, filtered, and concentrated to give the crude product, which was purified by silica column chromatography (petroleum ether: EtOAc = 7:1 ) to afford the title compound as a yellow solid which was characterized by LC MS. LC-MS: m/z (M+l ) = 233.
	With N,N-dimethyl-aniline; trichlorophosphate; at 140℃; for 16h;	8-Chloroquinazoline-2,4-diol (step B, 15 g, 75.8 rnmol) was added to POC13 (70 mL, 763 mmol, 10 equiv.) in small portions. Dirnethylaniline (3.7 g, 30.5 rnmol, 0.4 equiv.) was added. The reaction mixture was stirred in 140C for 16 hours. The mixture was cooled to room temperature, and added drop wise to ice-water (500 mL). The precipitate was collected and washed with ice-water. The solid was dissolved in DCM (500 rnL), dried over MgSO4, filtered, and concentrated to give the crude product, which was purified by silica column chromatography (petroleum ether: EtOAc = 7:1) to afford the title compound as a yellow solid which was characterized by LC/MS. LC-MS: m/z (M+1) = 233.
	With N,N-dimethyl-aniline; trichlorophosphate; at 140℃; for 16h;	8-Chloroquinazoline-2,4-diol (step B, 15 g, 75.8 mmol) was added to POCI3 (70 mL, 763 mmol, 10 equiv.) in small portions. Dimethylaniline (3.7 g, 30.5 mmol, 0.4 equiv.) was added. The reaction mixture was stirred in 140C for 16 hours. The mixture was cooled to room temperature, and added drop wise to ice-water (500 mL). The precipitate was collected and washed with ice-water. The solid was dissolved in DCM (500 mL), dried over MgS04, filtered, and concentrated to give the crude product, which was purified by silica column chromatography (petroleum ether: EtOAc = 7: 1) to afford the title compound as a yellow solid which was characterized by LC/MS. LC-MS: m/z (M+l) = 233.

References: [1]Patent: WO2014/101120,2014,A1 .Location in patent: Paragraph 0145.
[2]Patent: WO2014/105666,2014,A1 .Location in patent: Paragraph 0141; 0140.
[3]Patent: WO2014/101373,2014,A1 .Location in patent: Page/Page column 65; 66.
[4]RSC Advances,2017,vol. 7,p. 22360 - 22368.

14
[ 62484-29-1 ]
[ 1616708-00-9 ]

References: [1]Patent: WO2014/101373,2014,A1 .

15
[ 62484-29-1 ]
[ 1616708-01-0 ]

References: [1]Patent: WO2014/105666,2014,A1 .
[2]Patent: WO2014/101373,2014,A1 .

16
[ 62484-29-1 ]
[ 1616707-97-1 ]

References: [1]Patent: WO2014/105666,2014,A1 .
[2]Patent: WO2014/101373,2014,A1 .

17
[ 62484-29-1 ]
[ 1664398-52-0 ]

References: [1]Patent: WO2014/105666,2014,A1 .
[2]Patent: WO2014/101373,2014,A1 .

18
[ 62484-29-1 ]
[ 1616707-98-2 ]

References: [1]Patent: WO2014/105666,2014,A1 .
[2]Patent: WO2014/101373,2014,A1 .

19
[ 62484-29-1 ]
[ 19407-55-7 ]