129112-65-8|2,4-Dichloro-7-nitroquinazoline| Ambeed

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Quality Control of [ 129112-65-8 ] Purity: 95% SDS Specification

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Product Details of [ 129112-65-8 ]

CAS No. :	129112-65-8
Formula :	C₈H₃Cl₂N₃O₂
M.W :	244.03
SMILES Code :	O=[N+](C1=CC2=NC(Cl)=NC(Cl)=C2C=C1)[O-]
MDL No. :	MFCD18157742
InChI Key :	GTUFSSBJSUBKFD-UHFFFAOYSA-N
Pubchem ID :	12703362

Safety of [ 129112-65-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 129112-65-8 ]

* 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 [ 129112-65-8 ]

[ 129112-65-8 ] Synthesis Path-Downstream 1~35

1
[ 174565-63-0 ]
[ 129112-65-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With N-ethyl-N,N-diisopropylamine; trichlorophosphate; at 140℃; for 3h;	To a mixture of 7-nitroquinazoline-2,4(lH,3H)-dione (3.0 g, 14.4 mmol) in phosphoryl trichloride (20 mL) was added DIEA (3.7 g, 28.9 mmol) slowly at rt. The reaction mixture was heated to 140C for 3h. Then the reaction mixture was cooled and concentrated in vacuo. The residue was purified by column chromatography (PE:EA = 5: 1) to afford 2,4-dichloro-7-nitroquinazoline (2.5 g, 71%) as a yellow solid.1HNMR (400 MHz, CDCb): d 8.48-8.49 (m, 2H), 8.86 (s, 1H).
52%	With N-ethyl-N,N-diisopropylamine; trichlorophosphate; at 140℃; for 3h;	7-Nitroquinazoline-2,4(1H,3H)-dione (2a, 1.03 g, 5 mmol), DIPEA (1.17 mL, 10 mmol), and POCl3 (5.0 mL) were mixed and refluxed at 140 C for 3 h. The solution was cautiously poured into crushed ice and stirred vigorously. This aqueous mixture was extracted with CH2Cl2, the combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The crystalline solid was redissolved in CH2Cl2, filtered over a pad of silica using CH2Cl2 as eluent. Removal of the organic solvent gave 3a as gray solid (630 mg, 52% yield, Rf = 0.31 in 1:10 EtOAc/PE). 3a was used for the following reaction without further purification.
	With trichlorophosphate; In 2,3,5-trimethyl-pyridine; water; ethyl acetate; acetonitrile;	b) 18.6 ml (0.204 mol) of phosphorus oxychloride were added to a solution of 3.5 g (0.01 7 mol) of 7-nitro-1,2,3,4-tetrahydroquinazoline-2,4-dione and 6.5 ml (0.051 mol) of collidine in 60 ml of acetonitrile and the mixture was subsequently heated at reflux for 4 hrs. The solvent was removed on a rotary evaporator and the residue was partitioned between 300 ml of water and 300 ml of ethyl acetate. The organic phase was washed with 200 ml of saturated NaHCO3 solution and 2* with 200 ml of saturated sodium chloride solution and finally dried over sodium sulphate. After filtration and concentration the residue was chromatographed over Florisil with methylene chloride as the eluent. 2.46 g (60%) of 2,4-dichloro-7-nitroquinazoline were obtained as yellow crystals; MS: me/e=243, 245 (M+).

	With triethylamine; trichlorophosphate; at 115℃; for 17h;	General procedure: Anthranilic acids (3, 29.1 mmol, 1 eq) and urea (582.8 mmol, 20 eq) were poured into 100 mL round bottom flask. Then, the reaction mixture was heated at 150 oC for 20 h. The reaction was monitored by TLC. After the reaction was completed, it cooled down to room temperature. Then, 60 mL water was poured and the reaction mixture was heated at 100 oC for 1 h. The reaction mixture was cooled in ice bath and the white solid was precipitated. The white solid was filtered and washed with water and hexane. The residue (4, 28.3 mmol, 97%) was dried in vacuo and used next step without further purification. The chemical yield of first reaction was usually around 90%. The compound 4 (28.3 mmol, 1 eq) was dissolved in triethylamine (56.6 mmol, 2 eq). Then, POCl3 (254.5 mmol, 9 eq) was slowly added to the reaction mixture. The reaction mixture was heated at 115 oC for 17 h. The reaction was monitored by TLC. After the completion of the reaction, the reaction solvents were evaporated with toluene several times. The residue was diluted with water and extracted with ethyl acetate several times. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude 5 (25.2 mmol) was used in next step without further purification. The crude 5 (25.2 mmol) was dissolved in 2 N NaOH solution (75.6 mmol, 38 mL, 3 eq) and was stirred at room temperature for 20 h. The reaction mixture was cooled to room temperature. Acetic acid (75.6 mmol, 3 eq) was added to the reaction mixture. The aqueous phase was extracted with ethyl acetate and the combined organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford crude 6 (19.4 mmol), which was used in next step without further purification. To a 25 mL round bottom flask were added crude 6 (0.93 mmol), anilines (7, 2.8 mmol, 3 eq), and DMF (3.1 mL). The reaction mixture was stirred at 85 oC for 16 h. The reaction mixture was cooled to room temperature and precipitates were formed. The precipitates were washed with water and hexane thoroughly. The residue (8, 0.88 mmol, 94%) was dried in vacuo. If the precipitates were not formed, the reaction mixture was purified by prep HPLC (Shim-pack PREP-ODS, H2O:CH3CN:CH3OH=40:30:30 to H2O:CH3CN:CH3OH=1:49.5:49.5, flow rate=12 mL/min, 40 oC, λ=254 nm, retention time : 30 min). The chemical yields for each final products are described below.
	With trichlorophosphate; at 0 - 110℃; for 16h;	To a stirred solution of <strong>[174565-63-0]7-nitroquinazoline-2,4(1H,3H)-dione</strong> (10.3 g, 49.76 mmol) in phosphorus oxychloride (48 mL, 497.58 mmol) and N, N-diisopropylethylamine (13 mL, 74.64 mmol) at 0 C and the mixture was heated to 110 C for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with crushed ice and stirred for 10 min. The resulting solids were filtered and dried under vacuum to give the desired product. LCMS(m/z) 244.11 [M+H]+.

References: [1]Patent: WO2021/11796,2021,A1 .Location in patent: Paragraph 00226.
[2]European Journal of Medicinal Chemistry,2016,vol. 108,p. 644 - 654.
[3]Journal of the Chemical Society,1948,p. 1759,1765.
[4]Patent: US5688803,1997,A .
[5]Bioorganic and Medicinal Chemistry Letters,2021,vol. 39.
[6]Patent: WO2021/130638,2021,A1 .Location in patent: Paragraph 1054.

2
[ 129112-65-8 ]
[ 100-36-7 ]
[ 76004-46-1 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 127 - 140.

3
[ 129112-65-8 ]
[ 129112-64-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; at 20℃; for 20.0h;	General procedure: Anthranilic acids (3, 29.1 mmol, 1 eq) and urea (582.8 mmol, 20 eq) were poured into 100 mL round bottom flask. Then, the reaction mixture was heated at 150 oC for 20 h. The reaction was monitored by TLC. After the reaction was completed, it cooled down to room temperature. Then, 60 mL water was poured and the reaction mixture was heated at 100 oC for 1 h. The reaction mixture was cooled in ice bath and the white solid was precipitated. The white solid was filtered and washed with water and hexane. The residue (4, 28.3 mmol, 97%) was dried in vacuo and used next step without further purification. The chemical yield of first reaction was usually around 90%. The compound 4 (28.3 mmol, 1 eq) was dissolved in triethylamine (56.6 mmol, 2 eq). Then, POCl3 (254.5 mmol, 9 eq) was slowly added to the reaction mixture. The reaction mixture was heated at 115 oC for 17 h. The reaction was monitored by TLC. After the completion of the reaction, the reaction solvents were evaporated with toluene several times. The residue was diluted with water and extracted with ethyl acetate several times. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude 5 (25.2 mmol) was used in next step without further purification. The crude 5 (25.2 mmol) was dissolved in 2 N NaOH solution (75.6 mmol, 38 mL, 3 eq) and was stirred at room temperature for 20 h. The reaction mixture was cooled to room temperature. Acetic acid (75.6 mmol, 3 eq) was added to the reaction mixture. The aqueous phase was extracted with ethyl acetate and the combined organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford crude 6 (19.4 mmol), which was used in next step without further purification. To a 25 mL round bottom flask were added crude 6 (0.93 mmol), anilines (7, 2.8 mmol, 3 eq), and DMF (3.1 mL). The reaction mixture was stirred at 85 oC for 16 h. The reaction mixture was cooled to room temperature and precipitates were formed. The precipitates were washed with water and hexane thoroughly. The residue (8, 0.88 mmol, 94%) was dried in vacuo. If the precipitates were not formed, the reaction mixture was purified by prep HPLC (Shim-pack PREP-ODS, H2O:CH3CN:CH3OH=40:30:30 to H2O:CH3CN:CH3OH=1:49.5:49.5, flow rate=12 mL/min, 40 oC, λ=254 nm, retention time : 30 min). The chemical yields for each final products are described below.
	With sodium hydroxide; In tetrahydrofuran; at 0 - 20℃; for 2.0h;	To a stirred solution of <strong>[129112-65-8]2,4-dichloro-7-nitroquinazoline</strong> (20 g, 82.3 mmol) in THF (5 mL) was added 1M NaOH solution (197 mL, 197.53 mmol) at 0 C and the mixture was stirred for 2 h at RT. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was acidified with acetic acid to pH ~ 5 at 0 C. The resulting solids were filtered and dried under vacuum to give the desired product. LCMS(m/z) 226.21 [M+H]+.

References: [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 681 - 687.
[2]Bioorganic and Medicinal Chemistry Letters,2021,vol. 39.
[3]Patent: WO2021/130638,2021,A1 .Location in patent: Paragraph 1055.

4
[ 129112-65-8 ]
[ 76004-97-2 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 127 - 140.

5
[ 129112-65-8 ]
[ 129112-62-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 681 - 687.

6
[ 129112-65-8 ]
[ 129112-52-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 681 - 687.

7
[ 129112-65-8 ]
[ 129112-50-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 681 - 687.

8
[ 129112-65-8 ]
[ 129112-48-7 ]

References: [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 681 - 687.

9
[ 129112-65-8 ]
2-(4-Methyl-1-piperazinyl)-7-nitro-4(3H)-quinazolinone Hydrochloride [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 681 - 687.

10
[ 619-17-0 ]
[ 129112-65-8 ]

References: [1]Journal of the Chemical Society,1948,p. 1759,1765.
[2]European Journal of Medicinal Chemistry,2016,vol. 108,p. 644 - 654.
[3]Patent: WO2021/11796,2021,A1 .
[4]Bioorganic and Medicinal Chemistry Letters,2021,vol. 39.
[5]Patent: WO2021/130638,2021,A1 .

11
[ 129112-65-8 ]
[ 174565-64-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ice-water; dimethyl sulfoxide; butan-1-ol;	c) 1.574 g (0.015 mol) of ethyl carbazate were added to a solution of 2.45 g (0.01 mol) of <strong>[129112-65-8]2,4-dichloro-7-nitroquinazoline</strong> in 100 ml of dimethyl sulphoxide. The reaction mixture was stirred at RT for 2 hrs. and then poured on to ice-water. The brown precipitate was filtered off and dried. The brown crystals were suspended in 20 ml of n-butanol and the suspension was heated to 90 C. for 2 hrs. The mixture was left to cool to room temperature, the crystals were filtered off and dried in a vacuum. 1.77 g (60%) of ethyl 7-nitro-2-hydroxy-4-quinazolinecarbazate were obtained as yellow crystals.

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

12
[ 504-15-4 ]
[ 129112-65-8 ]
[ 1242243-76-0 ]
C₃₀H₁₈N₆O₈ [ No CAS ]

References: [1]European Journal of Organic Chemistry,2010,p. 4122 - 4129.

13
[ 129112-65-8 ]
C₄₅H₆₆N₈O₈ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2315 - 2325.

14
[ 129112-65-8 ]
N₂-{4-[(3-cyclohexylaminopropylamino)methyl]benzyl}-7-nitro-N₄-piperidin-4-yl-quinazoline-2,4-diamine hydrochloride salt [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2315 - 2325.

15
[ 129112-65-8 ]
[ 87120-72-7 ]
C₁₈H₂₂ClN₅O₄ [ No CAS ]