16499-62-0|4-Chloro-7-fluoroquinazoline| Ambeed

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Quality Control of [ 16499-62-0 ] Purity: 95% SDS Specification

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Product Details of [ 16499-62-0 ]

CAS No. :	16499-62-0
Formula :	C₈H₄ClFN₂
M.W :	182.58
SMILES Code :	FC1=CC2=NC=NC(Cl)=C2C=C1
MDL No. :	MFCD08236729
InChI Key :	JHBYQJRHJVEKPK-UHFFFAOYSA-N
Pubchem ID :	16227013

Safety of [ 16499-62-0 ]

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

Application In Synthesis of [ 16499-62-0 ]

* 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 [ 16499-62-0 ]

[ 16499-62-0 ] Synthesis Path-Downstream 1~35

1
[ 16499-57-3 ]
[ 16499-62-0 ]

Yield	Reaction Conditions	Operation in experiment
~ 100%	With thionyl chloride;Heating / reflux;	7-Fluoro-3H-quinazolin-4-one (8.2 g, 50 mmol) is heated at reflux in thionyl chloride (80 mL). Concentration affords the expected 4-Chloro-7-fluoro-quinazoline (9.1 g, quant).
	With thionyl chloride; N,N-dimethyl-formamide; for 8h;Reflux;	General procedure: A mixture of 4-quinazolone analogues 2a-2j (8.0 mmol) in SOCI2 (27.4 mL) containing DMF (2 drops) was refluxed for 8 h. SOCI2 was removed under reduced pressure and the residue was dissolved in DCM. The solution was washed with saturated NaHCO3 solution and brine, respectively, dried over anhydrous Na2S04 and then concentrated under reduced pressure to yield the compounds 3a-3j (65.1-88.9percent yield) as white or off-white solid.

References: [1]Patent: US2008/70935,2008,A1 .Location in patent: Page/Page column 54.
[2]Journal of Medicinal Chemistry,2021,vol. 64,p. 14477 - 14497.
[3]Synthetic Communications,2011,vol. 41,p. 3644 - 3653.
[4]Journal of Medicinal Chemistry,1996,vol. 39,p. 267 - 276.
[5]Organic Letters,2010,vol. 12,p. 552 - 555.
[6]MedChemComm,2014,vol. 5,p. 1290 - 1296.
[7]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4885 - 4888.
[8]Archiv der Pharmazie,2019,vol. 352.
[9]Bioorganic Chemistry,2020,vol. 98.
[10]Chemistry and biodiversity,2020,vol. 17.

2
[ 16499-62-0 ]
[ 591-19-5 ]
[ 198961-95-4 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 267 - 276.

3
[ 16499-62-0 ]
[ 130339-51-4 ]
[1-(4-difluoromethoxy-phenyl)-propyl]-(7-fluoro-quinazolin-4-yl)-amine [ No CAS ]

References: [1]Pesticide Science,1999,vol. 55,p. 896 - 902.

5
[ 16499-62-0 ]
[ 765-30-0 ]
Cyclopropyl-(7-fluoro-quinazolin-4-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In dichloromethane; at 20℃;	4-Chloro-7-fluoro-quinazoline (0.73 g, 4 mmol) and cyclopropylamine (0.23 g, 4 mmol) are stirred in dichloromethane at ambient temperature overnight. The solid product is precipitated with hexanes, filtered, and washed with hexane and ethyl acetate, affording 0.3 g of desired Cyclopropyl-(7-fluoro-quinazolin-4-yl)-amine. The filtrate is concentrated and precipitated with hexanes, yielding an additional 0.35, for a combined yield of 80%. LC/MS m/z=204 [M+H]+).

References: [1]Patent: US2008/70935,2008,A1 .Location in patent: Page/Page column 54.

6
[ 16499-62-0 ]
N⁴-(3-Bromo-phenyl)-N⁷-methyl-quinazoline-4,7-diamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 267 - 276.

7
[ 16499-62-0 ]
N⁴-(3-Bromo-phenyl)-N⁷-ethyl-quinazoline-4,7-diamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 267 - 276.

8
[ 16499-62-0 ]
N⁴-(3-Bromo-phenyl)-N⁷,N⁷-dimethyl-quinazoline-4,7-diamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 267 - 276.

9
[ 99724-19-3 ]
[ 16499-62-0 ]
[1-(7-fluoro-quinazolin-4-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20 - 100℃; for 0.375h;	A vial was charged with 4-chloro-7-fluoro-quinazoline (2.00 g, 11.0 mmol) (WO 9609294 A1), pyrrolidin-3-yl-carbamic acid tert-butyl ester (2.05 g, 11.0 mmol), DMSO (2.64 mL), and DIPEA (2.10 mL, 12.0 mmol) in quick succession. The mixture was stirred at "rt" for 20 min, during which time the reaction spontaneously warmed and became a homogeneous reddish-brown solution. The reaction was then stirred at 100 C. for 2.5 min to ensure complete reaction. The solution was shaken with water (20 mL) to dissolve the DMSO into the aqueous phase, and was extracted with EtOAc (120 mL). The organic layer was washed with 4 M NaCl (120 mL) and dried (Na2SO4). Upon addition of Na2SO4 to the organic phase, the title compound began to precipitate out. This was collected by filtration (easily decanted from the wet drying agent), dried, and powdered to afford the title compound as an off-white powder (1.42 g, 39%).
39%	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20 - 100℃; for 0.375h;	EXAMPLE NO. 70; 1-(4-Isopropyl-phenyl)-3-(1-{7-[2-(2-oxo-pyrrolidin-1-yl)-ethoxy]-quinazolin-4-yl}-pyrrolidin-3-yl)-urea (Compound No. 70); a. [1-(7-Fluoro-quinazolin-4-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester; A vial was charged with 4-chloro-7-fluoro-quinazoline (2.00 g, 11.0 mmol) (WO 9609294 A1), pyrrolidin-3-yl-carbamic acid tert-butyl ester (2.05 g, 11.0 mmol), DMSO (2.64 mL), and DIPEA (2.10 mL, 12.0 mmol) in quick succession. The mixture was stirred at “rt” for 20 min, during which time the reaction spontaneously warmed and became a homogeneous reddish-brown solution. The reaction was then stirred at 100 C. for 2.5 min to ensure complete reaction. The solution was shaken with water (20 mL) to dissolve the DMSO into the aqueous phase, and was extracted with EtOAc (1×20 mL). The organic layer was washed with 4 M NaCl (1×20 mL) and dried (Na2SO4). Upon addition of Na2SO4 to the organic phase, the title compound began to precipitate out. This was collected by filtration (easily decanted from the wet drying agent), dried, and powdered to afford the title compound as an off-white powder (1.42 g, 39%).

References: [1]Patent: US2006/281771,2006,A1 .Location in patent: Page/Page column 74.
[2]Patent: US2007/4763,2007,A1 .Location in patent: Page/Page column 62-63.

10
[ 124443-68-1 ]
[ 16499-62-0 ]
[ 916731-79-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20℃; for 2.61667 - 2.63333h;	EXAMPLE 65; 4-[7-(3-Methanesulfonylamino-propoxy)-quinazolin-4-yl]-piperidine-1-carboxylic acid (4-isopropoxy-phenyl)-amide; a. 4-(7-Fluoro-quinazolin-4-yl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester; A mixture of 4-chloro-7-fluoro-quinazoline (2.87 g, 15.4 mmol) (WO 9609294 A1) and piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (4.15 g, 17.1 mmol), as prepared in Example 1b, was placed in a -78 C. bath for 5 min under argon before adding a 1.08 M LiHMDS/THF solution (17.8 mL, 19.2 mmol) rapidly by syringe along the sides of the flask (to allow cooling and dispersion of the hindered base before reaction with the ester). Following completion of LiHMDS/THF addition, the reaction was manually swirled in the -78 C. bath for 2-3 min before removing the cold bath and allowing the mixture to stir with gradual warming to rt. After 2.5 h stirring at rt, the dark brown homogeneous solution was quenched with 1.0 M NaH2PO4 (38 mL) and extracted with DCM (1×150 mL and 1×25 mL). The organic layers were combined, dried (Na2SO4), and concentrated under reduced pressure, and subject to high vacuum at 90 C. with toluene chasers (3×10 mL) to provide the crude title compound as an opaque thick yellow oil that was used in the next step without further purification (6.83 g, “114%” crude yield). 1H-NMR (300 MHz, CDCl3) δ 9.26 (s, 1H), 8.11 (dd, 1H), 7.70 (dd, 1H), 7.36 (ddd, 1H), 3.74-3.64 (m, 2H), 3.62-3.51 (m, 2H), 3.61 (s, 3H), 2.47-2.38 (br m, 4H), 1.46 (s, 9H). LC/MS (ESI): calcd mass 389.2, found 390.1 (MH)+.

References: [1]Patent: US2006/281772,2006,A1 .Location in patent: Page/Page column 79-80.

11
[ 1206694-33-8 ]
[ 16499-62-0 ]
[ 1206694-07-6 ]

References: [1]Organic Letters,2010,vol. 12,p. 552 - 555.

12
[ 1206694-33-8 ]
[ 16499-62-0 ]
[ 1206694-27-0 ]

References: [1]Organic Letters,2010,vol. 12,p. 552 - 555.

13
[ 31230-17-8 ]
[ 16499-62-0 ]
[ 1206694-23-6 ]

References: [1]Organic Letters,2010,vol. 12,p. 552 - 555.

14
[ 31230-17-8 ]
[ 16499-62-0 ]
[ 1206694-03-2 ]

References: [1]Organic Letters,2010,vol. 12,p. 552 - 555.

15
[ 1020150-22-4 ]
[ 16499-62-0 ]
[ 1586047-39-3 ]

References: [1]ChemMedChem,2014,vol. 9,p. 590 - 601.

16
[ 2016-57-1 ]
[ 16499-62-0 ]
N-decyl-7-fluoroquinazolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In isopropyl alcohol; for 6h;Reflux;	A mixture of 1-decylamine (1.2 mL, 6.0 mmol), <strong>[16499-62-0]4-chloro-7-fluoroquinazoline</strong> (1.1 g, 6.0 mmol), and TEA (1.3 mL, 9.3 mmol) in 10 mL of IPA was heated at reflux for 6 hr. Then, the volatile components were evaporated, and the residue was partitioned between DCM (400, 300 mL) and 5% Na2C03 (400 mL). The organic phases were dried over anhydrous Na2S04, filtered through a pad of silica gel, washing with 10% MeOH/DCM, and concentrated. The product was crystallized from EA/Hex.

References: [1]Patent: WO2014/120995,2014,A2 .Location in patent: Page/Page column 159.

17
[ 2475-81-2 ]
[ 16499-62-0 ]

References: [1]MedChemComm,2014,vol. 5,p. 1290 - 1296.

18
5-nitro-2,3-dihydro-1H-inden-2-amine [ No CAS ]
[ 16499-62-0 ]
C₁₇H₁₃FN₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In isopropyl alcohol; at 65℃; for 2h;Inert atmosphere;	To a solution of compound SP-0011321-023 (500 mg, 2.75 mmol) and 5-nitro-2,3- dihydro-1H-inden-2-amine (490 mg, 2.75 mmol) in isopropyl alcohol (30 mL) was added triethylamine (2.8 g, 27.5 mmol). The resulting solution was heated to 65 C under N2 for 2 h. The mixture was cooled down and excess of isopropyl alcohol was removed by rotary evaporation to give the crude compound SP-0011321-025 (898 mg).

References: [1]Patent: WO2014/145512,2014,A2 .Location in patent: Page/Page column 83; 84.

19
[ 446-32-2 ]
[ 16499-62-0 ]

References: [1]Patent: WO2014/145512,2014,A2 .
[2]Patent: US2008/70935,2008,A1 .
[3]Archiv der Pharmazie,2019,vol. 352.
[4]Chemistry and biodiversity,2020,vol. 17.
[5]Patent: WO2020/128981,2020,A1 .
[6]Journal of Medicinal Chemistry,2021,vol. 64,p. 14477 - 14497.

20
[ 16499-57-3 ]
[ 16499-62-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With thionyl chloride; In N,N-dimethyl-formamide; toluene; for 10h;Reflux;	To a suspension of 7-fluoroquinazolin-4-ol compound A (6.32 g, 38.5 mmol) in dry PhMe (30 mL), SOCk (22 mL, 7.7 eq.) and DMF (2.6 mL) were added. The resulting mixture was refluxed for 10 h. The mixture was then cooled to room temperature, quenched with water (200 mL), and extracted with ethyl acetate (EtOAc; 170 mL). The combined organic extracts were washed with water (300 mL) and brine (30 mL), dried over sodium sulfate (Na2S04), and concentrated to afford compound B (6.08 g, 86%) as a yellow solid. LCMS (ESI) m/z calculated for C8H4CIFN2: 182, 184; found: 183, 185 [M+H]+.1H-NMR (400 MHz, CDCl3) d 9.04 (s, 1H), 8.33 (dd, J = 9.2 Hz,4JF,H= 6.0 Hz, 1H), 7.71 (dd,3JF,H= 9.2 Hz, J= 2.4 Hz, 1H), 7.52 (ddd, J = 9.2, 2.4 Hz,3JF,H= 8.4 Hz, 1H).
	With thionyl chloride; N,N-dimethyl-formamide; for 5h;Reflux;	To the crude product SP-0011321-021 (0.82 g, 5 mmol) was added thionyl dichloride (12.0 g, 0.1 mol) and catalytic amount of anhydrous DMF (0.5 mL). The reaction mixture was heated to reflux for 5 h. After the reaction was completed, the mixture was cooled down and excess thionyl dichloride was removed by rotary evaporation. The resulting crude product SP-0011321-023 (950 mg) was used in the next step of reaction without further purification.

References: [1]Patent: WO2020/210481,2020,A1 .Location in patent: Page/Page column 12; 13.
[2]Patent: WO2014/145512,2014,A2 .Location in patent: Page/Page column 83; 84.

21
[ 16499-62-0 ]
C₁₇H₁₅FN₄ [ No CAS ]

References: [1]Patent: WO2014/145512,2014,A2 .

22
[ 16499-62-0 ]
C₁₉H₁₇FN₄O [ No CAS ]

References: [1]Patent: WO2014/145512,2014,A2 .

23
[ 16499-62-0 ]
C₁₉H₁₇FN₄O₂ [ No CAS ]

References: [1]Patent: WO2014/145512,2014,A2 .

24
[ 16499-62-0 ]
C₂₂H₂₃FN₄O₂ [ No CAS ]

References: [1]Patent: WO2014/145512,2014,A2 .

25
[ 16499-62-0 ]
C₁₇H₁₆FN₅OS [ No CAS ]

References: [1]Patent: WO2014/145512,2014,A2 .

26
[ 16499-62-0 ]
[ 106006-83-1 ]
C₁₅H₁₄FN₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With triethylamine; In isopropyl alcohol; at 70℃;Inert atmosphere;	A mixture of <strong>[16499-62-0]4-chloro-7-fluoroquinazoline</strong> (100 mg, 0.55 mmol), 4,5,6,7- tetrahydrobenzo[d]thiazole-2,6-diamine (180 mg, 0.55 mmol) and triethylamine (1.0 mL, 7.2 mmol) in isopropyl alcohol (5 mL) was heated to 70 C under N2 overnight. The reaction mixture was cooled down and excess isopropyl alcohol was removed by rotary evaporation to give a residue. The residue was purified by Prep-HPLC to give A31-028 as a yellow solid (84 mg, yield: 48%). LC-MS 316 (M+H), purity 100% (UV 214 nm); ‘H NMR (400 MHz, MeOD-d4) ö 8.47 (s, 1 H), 8.29-8.33 (m, 1 H), 7.32-7.37 (m, 2 H), 4.70- 4.72 (m, 1 H), 3.05-3.10 (m, 1 H), 2.66-2.72 (m, 3 H), 2.21-224 (m, 1 H), 2.03-2.06 (m, 1H).

References: [1]Patent: WO2014/145512,2014,A2 .Location in patent: Page/Page column 129; 130.

27
[ 39979-08-3 ]
[ 16499-62-0 ]
7-((7-fluoroquinazolin-4-yl)amino)-N-hydroxyheptanamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4885 - 4888.

28
[ 39979-08-3 ]
[ 16499-62-0 ]
C₁₆H₂₀FN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In isopropyl alcohol; at 90℃; for 6h;	General procedure: 4-chloroqui nazoline analogues 3a-3j (10 mmol) and methyl 6-aminocaproate or methyl 7-aminoheptoate (11mmol) are dissolved in 30ml isopropanol and further added with 4 ml triethylamine. The reaction mixture is reacted under reflux for 6h followed by cooling to room temperature, and then added with a proper amount of water and extracted with ethyl acetate three times. The ethyl acetate layer is collected, dried over anhydrous Na2S04 and then concentrated under reduced pressure to get ester intermediates 4a-4l without further purification.

References: [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4885 - 4888.

29
[ 16499-62-0 ]
[ 98-80-6 ]
7-fluoro-4-phenylquinazoline [ No CAS ]