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[ CAS No. 115643-59-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 115643-59-9
Chemical Structure| 115643-59-9
Chemical Structure| 115643-59-9
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Product Details of [ 115643-59-9 ]

CAS No. :115643-59-9 MDL No. :MFCD00816881
Formula : C7H7FN2O Boiling Point : -
Linear Structure Formula :- InChI Key :REPZELLBLWMUAB-UHFFFAOYSA-N
M.W :154.14 Pubchem ID :2778939
Synonyms :

Calculated chemistry of [ 115643-59-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 38.9
TPSA : 69.11 Ų

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) : -7.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.76
Log Po/w (XLOGP3) : 0.02
Log Po/w (WLOGP) : 0.93
Log Po/w (MLOGP) : 1.02
Log Po/w (SILICOS-IT) : 0.68
Consensus Log Po/w : 0.68

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.15
Solubility : 11.0 mg/ml ; 0.0715 mol/l
Class : Very soluble
Log S (Ali) : -1.02
Solubility : 14.6 mg/ml ; 0.0948 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.89
Solubility : 1.98 mg/ml ; 0.0128 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 115643-59-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 115643-59-9 ]

* 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 [ 115643-59-9 ]

[ 115643-59-9 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 122-51-0 ]
  • [ 115643-59-9 ]
  • [ 436-72-6 ]
YieldReaction ConditionsOperation in experiment
at 130℃; for 46h; 2.7 g (1 1.4 mmol) of <strong>[115643-59-9]2-amino-6-fluorobenzamide</strong> (ABCR, Karlsruhe, Germany) in 50 ml triethylorthoformate (Fluka, Buchs, Switzerland) is heated for 46 h at 1300C. The reaction mixture is evaporated to dryness in vacuo. The residue is triturated in hexane/EtOAc and the solid is filtered and dry to give the title compound as as an off-white solid. ES-MS: 243, 245 (M + H)+; analytical HPLC: trthetat = 2.49min (Grad 1 ).
  • 2
  • [ 115643-59-9 ]
  • 5-fluoro-2-[3-(4-phenyl-3,6-dihydro-2<i>H</i>-pyridin-1-yl)-propyl]-3<i>H</i>-quinazolin-4-one [ No CAS ]
  • 3
  • [ 115643-59-9 ]
  • [ 437998-58-8 ]
  • 5
  • [ 77326-36-4 ]
  • [ 115643-59-9 ]
  • [ 898554-22-8 ]
YieldReaction ConditionsOperation in experiment
64% NaNO2 (139.7 mg, 2.02 mmol) was added to a suspension of 2-amino-6- fluorobenzamide (~282 mg, 1.8 mmol) and 2-amino-6-fluorobenzonitrile (~46 mg, 0.34 mmol) in HCl (2 N, 5 mL) at 0 C. The mixture was stirred for 1 h. Na2CO3 (20 % soln) was added until the solution was basic and the resulting solid removed via vacuum filtration. The filtrate was then acidified with HCl (2 N) and the precipitate collected via vacuum filtration to provide 178.5 mg (64 %) of the title compound. 1H NMR (DMSO- d6) delta 8.08 (td, 1 H), 8.05 - 7.97 (m, 1 H), 7.70 (ddd, 1 H). MS (ES) 164 (M - H), 166 (M + H).
  • 6
  • [ 1121-60-4 ]
  • [ 115643-59-9 ]
  • 2-fluoro-6-[(pyridin-2-ylmethylidene)amino]benzamide [ No CAS ]
  • 7
  • [ 98-01-1 ]
  • [ 115643-59-9 ]
  • 2-fluoro-6-[(furan-2-ylmethylidene)amino]benzamide [ No CAS ]
  • 8
  • [ 98-01-1 ]
  • [ 115643-59-9 ]
  • [ 1098336-95-8 ]
  • 9
  • [ 10400-19-8 ]
  • [ 115643-59-9 ]
  • C13H10FN3O2 [ No CAS ]
  • 10
  • [ 14254-57-0 ]
  • [ 115643-59-9 ]
  • C13H10FN3O2 [ No CAS ]
  • 11
  • [ 455-19-6 ]
  • [ 115643-59-9 ]
  • [ 1098337-02-0 ]
  • 12
  • [ 3739-94-4 ]
  • [ 115643-59-9 ]
  • C21H15F2N5O4 [ No CAS ]
  • 13
  • [ 626-19-7 ]
  • [ 115643-59-9 ]
  • [ 1098337-00-8 ]
  • 14
  • [ 77326-36-4 ]
  • [ 115643-59-9 ]
YieldReaction ConditionsOperation in experiment
94% With water; potassium carbonate; In water; at 150℃; for 0.5h;Microwave irradiation; General procedure: Adapted from a literature procedure,1 the appropriate organonitrile (1.0 eq.) and K2CO3(0.2eq.)wereaddedtoamicrowavetubewithastir-barwithdeionizedwater(8.5mLpermmolsubstrate).Afterirradiationundermicrowaveat150Cfor30minutes,thereactionmixturewascooled,extractedwithEtOAc(320mL),thecombinedphasesdriedoverMgSO4andexcesssolventremovedinvacuo.TheresiduewaspurifiedbyFCC,ifrequired,togivethetitlecompound.
With sulfuric acid; at 65℃; for 1.5h; A solution of2-amino-6-fluorobenzonitrile (10.0 g) in H2S04 (75.0 mL) wasstirred for 1.5 h at 65 C. Then the mixture was poured into ice and brought topH= 9 by 20% NaOH aqueous solution, followed by the extraction with ethylacetate three times. The combined organic layer were washed with brine anddried over Na2S04. It was filtered to remove insoluble matters and it wasconcentrated in vacuo to give compound 1-1 as a pale yellow solid.
A solution of 2-amino-6-fluorobenzonitrile (10.0 g) in H2S04 (75.0 mL) was stirred for 1.5 h at 65 C. Then the mixture was poured into ice and brought to pH = 9 by 20% NaOH aqueous solution, followed by the extraction with ethyl acetate three times. The combined organic layer were washed with brine and dried over Na2S04. It was filtered to remove insoluble matters and it was concentrated in vacuo to give compound 1-1 as a yellow solid.
  • 15
  • [ 108-24-7 ]
  • [ 115643-59-9 ]
  • [ 1379304-63-8 ]
  • 16
  • [ 459-57-4 ]
  • [ 115643-59-9 ]
  • [ 1098337-01-9 ]
  • 17
  • [ 123-11-5 ]
  • [ 115643-59-9 ]
  • 2-fluoro-6-[(4-methoxybenzylidene)amino]benzamide [ No CAS ]
  • 18
  • [ 90-02-8 ]
  • [ 115643-59-9 ]
  • 2-fluoro-6-[(2-hydroxybenzylidene)amino]benzamide [ No CAS ]
  • 19
  • [ 98-88-4 ]
  • [ 115643-59-9 ]
  • C14H11FN2O2 [ No CAS ]
  • 20
  • [ 97-51-8 ]
  • [ 115643-59-9 ]
  • 2-fluoro-6-[(2-hydroxy-5-nitrobenzylidene)amino]benzamide [ No CAS ]
  • 21
  • [ 4755-77-5 ]
  • [ 115643-59-9 ]
  • [ 869299-02-5 ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 3h; Step 1 To a solution of <strong>[115643-59-9]2-amino-6-fluorobenzamide</strong> (3.80 g, 24.7 mmol) and triethylamine (2.99 g, 29.6 mmol) in THF (50 mL) was added dropwise ethyl chloroglyoxylate (3.70 g, 27.1 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. The mixture was partitioned between ethyl acetate and water, and the organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was suspended in ethanol, and the insoluble material was collected by filtration to give ethyl ((2-(aminocarbonyl)-3-fluorophenyl)amino)(oxo)acetate as a white powder (4.95 g, 79%).
79% With triethylamine; In tetrahydrofuran; at 35℃; for 3h;Cooling with ice; Step 1 To a solution of <strong>[115643-59-9]2-amino-6-fluorobenzamide</strong> (3.80 g, 24.7 mmol) and triethylamine (2.99 g, 29.6 mmol) in THF (50 mL) was added dropwise ethyl chloroglyoxylate (3.70 g, 27.1 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hrs. The mixture was partitioned between ethyl acetate and water, and the organic layer was washed with saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The obtained concentrated residue was suspended in EtOH, and insoluble material was collected by filtration to give ethyl ((2-(aminocarbonyl)-3-fluorophenyl)amino)(oxo)acetate as a white powder (4.95 g, 79%).
  • 22
  • [ 590-86-3 ]
  • [ 115643-59-9 ]
  • [ 1086673-30-4 ]
  • 23
  • [ 558442-97-0 ]
  • [ 869937-03-1 ]
  • [ 115643-59-9 ]
  • C30H33F4N7O4 [ No CAS ]
  • 24
  • [ 5390-04-5 ]
  • [ 115643-59-9 ]
  • [ 1208003-39-7 ]
  • 25
  • [ 59046-72-9 ]
  • [ 115643-59-9 ]
  • [ 1226978-03-5 ]
  • 26
  • [ 107586-15-2 ]
  • [ 115643-59-9 ]
  • [ 1226978-06-8 ]
  • 27
  • 5-(4-fluorophenyl)-1,3-dioxolane-2,4-dione [ No CAS ]
  • [ 115643-59-9 ]
  • [ 1241915-00-3 ]
YieldReaction ConditionsOperation in experiment
[00293] Step A: 5 -(4-fluorophenyl)- 1, 3-dioxolane-2, 4-dione was prepared according to JACS, 2002 2870-2871. To <strong>[115643-59-9]2-amino-6-fluorobenzamide</strong> (550 mg, 3.5 mmol) in THF (15 mL) was added 5-(4-fluorophenyl)-l,3-dioxolane-2,4-dione (1049 mg, 5.35 mmol) and the mixture was heated at 50 0C overnight. The solvent was evaporated to afford crude 2-(2,2-difluoro-2-(4-fluorophenyl)acetamido)-4- methoxybenzamide and the crude mixture was dissolved in ethanol (12 mL), added aq potassium carbonate solution and heated the reaction mixture at 80 0C for overnight. The crude mixture was extracted with EtOAc and water and the EtOAc layer was concentrated in vacuum to afford (R,S)-5-fluoro-2-((4- fluorophenyl)(hydroxyl)methyl)quinazolin-4-ol (650 mg, %). LC-MS (ESI) m/z 290 (M + Na)+.
  • 28
  • [ 536-74-3 ]
  • [ 115643-59-9 ]
  • [ 1246861-71-1 ]
  • 29
  • [ 50270-27-4 ]
  • [ 115643-59-9 ]
  • [ 1246067-19-5 ]
  • 30
  • [ 59046-72-9 ]
  • [ 115643-59-9 ]
  • [ 1364405-93-5 ]
  • (R)-7-fluoro-4b,5-dihydro-12-phenylisoquinolino[2,1-a]quinazolin-6-one [ No CAS ]
  • 31
  • [ 221458-82-8 ]
  • [ 115643-59-9 ]
  • [ 1364406-25-6 ]
  • 32
  • [ 100-51-6 ]
  • [ 115643-59-9 ]
  • [ 1098336-86-7 ]
  • 33
  • [ 79544-29-9 ]
  • [ 115643-59-9 ]
  • 34
  • [ 115643-59-9 ]
  • 8-fluoro-3-ethyl-1H-isochromen-1-one [ No CAS ]
  • 35
  • [ 107-00-6 ]
  • [ 115643-59-9 ]
  • [ 1431758-13-2 ]
  • 36
  • [ 115643-59-9 ]
  • [ 1616069-02-3 ]
  • 37
  • [ 115643-59-9 ]
  • [ 1616069-08-9 ]
  • 38
  • [ 115643-59-9 ]
  • [ 1616238-76-6 ]
  • 39
  • [ 115643-59-9 ]
  • (R)-2-((7-carbamoyl-3-(1,3-dioxoisoindolin-2-yl)benzo[d]isothiazol-6-yl)amino)-1-((2R,6S)-6-methyl-3-oxo-4-(1-(6-(trifluoromethyl)pyridazin-4-yl)-1H-pyrazol-3-yl)morpholin-2-yl)-2-oxoethyl acetate [ No CAS ]
  • (S)-(3-(1,3-dioxoisoindolin-2-yl)-9-oxo-6,9-dihydroisothiazolo[5,4-f]quinazolin-7-yl)((2R,6S)-6-methyl-3-oxo-4-(1-(6-(trifluoromethyl)pyridazin-4-yl)-1H-pyrazol-3-yl)morpholin-2-yl)methyl acetate [ No CAS ]
  • 40
  • [ 115643-59-9 ]
  • [ 1616069-09-0 ]
  • 41
  • [ 115643-59-9 ]
  • [ 1616238-70-0 ]
  • 42
  • [ 115643-59-9 ]
  • [ 1616238-83-5 ]
  • 43
  • [ 115643-59-9 ]
  • [ 1616238-72-2 ]
  • 44
  • [ 115643-59-9 ]
  • [ 1616238-93-7 ]
  • 45
  • [ 115643-59-9 ]
  • [ 1616069-01-2 ]
YieldReaction ConditionsOperation in experiment
With iodine; silver sulfate; In ethanol; at 20℃; for 1.5h; To a suspension ofh (12.4 g) andAg2S04 (15.2 g) in EtOH (420 mL) wasadded compound 1-1 (7.50 g), and it was stirred for 1.5 hat room temperature.Then the reaction mixture was filtered with Celite. The filtrate was concentratedin vacuo to give a crude material of compound 1-2 as a pale brown solid, whichwas used in the next step without further purification.
With iodine; silver sulfate; In ethanol; at 20℃; for 1.5h; To a suspension of I2 (12.4 g) and Ag2S04 (15.2 g) in EtOH (420 mL) was added compound 1-1 (7.50 g), and it was stirred for 1.5 h at room temperature. Then the reaction mixture was filtered with Celite (Fluka) diatomite is diatomaceous earth. The filtrate was concentrated in vacuo to give a crude material of compound 1 -2 as a pale brown solid, which was used in the next step without further purification.
  • 46
  • [ 115643-59-9 ]
  • [ 1616069-03-4 ]
  • 47
  • [ 115643-59-9 ]
  • [ 1616069-07-8 ]
  • 48
  • [ 115643-59-9 ]
  • [ 1616068-51-9 ]
  • 49
  • [ 115643-59-9 ]
  • [ 1616069-12-5 ]
  • 50
  • [ 115643-59-9 ]
  • [ 1616068-54-2 ]
  • 51
  • [ 20260-53-1 ]
  • [ 115643-59-9 ]
  • C13H10FN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; dichloromethane; for 15h;Reflux; General procedure: To a solution of 2-aminobenzamide (1.0 mmol) and triethylamine (10.0 mmol) in tetrahydrofurane (1.0 ml) and dichloromethane (1.0 ml) was added aromatic acid chloride (1.0 mmol) in one portion. The reaction mixture was heated to reflux with stirring. After 15 h the solvents were removed in vacuo and obtained solid was dissolved in ethyl acetate (10.0 ml) and extracted with water (3.0 ml) three times. After evaporation of solvent the appropriate N-(2-carbamoylphenyl)arylamide was obtained. This compound was then dissolved in aqueous KOH (1M, 3.0 ml) and stirred with heating to 100 C for 10 h. The resulting solution was diluted with water (20.0 ml) and the resulting 2-arylquinazolin-4(3H)-one was filtered off and washed with water (20.0 ml). Treating this compound with POCl3 (10.0 mmol) in dimethylformamide (10.0 ml) at 80 C followed by decomposition of excess of POCl3 on ice (100 g) and neutralization with sodium hydroxide (20% aqueous solution) led to crude product. Appropriate 4-chloroquinazoline derivative was obtained after chromatography (CHCl3 with gradient of MeOH).
With triethylamine; In tetrahydrofuran; dichloromethane; for 15h;Reflux; General procedure: To a solution of 2-aminobenzamide (1.0 mmol) and triethylamine (10.0 mmol) in tetrahydrofurane (1.0 ml) and dichloromethane (1.0 ml) was added aromatic acid chloride (1.0 mmol) in one portion. The reaction mixture was heated to reflux with stirring. After 15 h the solvents were removed in vacuo and obtained solid was dissolved in ethyl acetate (10.0 ml) and extracted with water (3.0 ml) three times. After evaporation of solvent the appropriate N-{2- carbamoylphenyl)arylamide was obtained. This compound was then dissolved in aqueous KOH (IM, 3.0 ml) and stirred with heating to 100 C for 10 h. The resulting solution was diluted with water (20.0 ml) and the resulting 2-arylquinazolin-4(3H)-one was filtered off and washed with water (20.0 ml). Treating this compound with POCI3 (10.0 mmol) in dimethylformamide (10.0 ml) at 80 C followed by decomposition of excess of POCI3 on ice (100 g) and neutralization with sodium hydroxide (20% aqueous solution) led to crude product. Appropriate 4- chloroquinazoline derivative was obtained after chromatography (CHC13 with gradient of MeOH).
  • 52
  • [ 115643-59-9 ]
  • [ 1623478-68-1 ]
  • 53
  • [ 115643-59-9 ]
  • C13H8FN3O [ No CAS ]
  • 54
  • [ 77287-34-4 ]
  • [ 115643-59-9 ]
  • [ 436-72-6 ]
YieldReaction ConditionsOperation in experiment
55% With ytterbium(III) triflate; In 1,3,5-trimethyl-benzene; at 165℃; for 6h;Inert atmosphere; General procedure: A mixture of 2-aminobenzamide (1, 4.0 mmol), carboxamide (2, 6.0 mmol), Yb(OTf)3 (0.20 mmol,5.0 mol%), and mesitylene (5.0 mL) was placed in a 20-mL Pyrex flask equipped with a magnetic stirring bar and a reflux condenser under a flow of argon. The reaction was carried out at 120-165 oC (bath temp.) for 6 h with stirring. Then, the reaction mixture was cooled to room temperature, and analyzed by GLC, GC-MS (EI), and LC-MS (ESI). After evaporation of mesitylene under vacuum,the products (3) were isolated by recrystallization from MeOH/hexane and/or medium pressure column chromatography on silica gel (eluent: EtOAc/hexane = 50/50 ~ EtOAc 100%. For 3j, eluent:MeOH/CHCl3 = 50/50). 1H NMR spectra were recorded at 400 MHz, and 13C NMR spectra wererecorded at 100 MHz in DMSO-d6. The analytical and spectral data of 3a-e,38 3f,39 3g,40 3h,41 and3j,42 were consistent with those reported previously. The product, 3i, was characterized below.
  • 55
  • [ 53293-00-8 ]
  • [ 115643-59-9 ]
  • 6,7,8,9-tetrahydro-1-fluoro-9-methylene-11H-pyrido[2,1-b]quinazolin-11-one [ No CAS ]
  • 56
  • [ 53293-00-8 ]
  • [ 115643-59-9 ]
  • 2-(4-pentynyl)-5-fluoro-4(3H)-quinazolinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of 5-hexynoic acid (3.0 mmol) in dryCH2Cl2 (5 mL) was added EDCI (3.1 mmol) and HOBt(3.1 mmol). The resulting mixture was stirred at rt for 2 h. Then substituted or unsubstituted 2-aminobenzamide (3.0 mmol) wasadded, and the reaction mixture was stirred at rt for 12 h whilebeing monitored by TLC. After the addition of H2O (10 mL) themixture was extracted with ethyl acetate (3 × 20 mL). Theorganic layers were combined and concentrated under vacuumto give the amide intermediate.
  • 57
  • [ 6089-09-4 ]
  • [ 115643-59-9 ]
  • 2-(3-butynyl)-5-fluoro-4(3H)-quinazolinone [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: To a solution of 5-hexynoic acid (3.0 mmol) in dryCH2Cl2 (5 mL) was added EDCI (3.1 mmol) and HOBt(3.1 mmol). The resulting mixture was stirred at rt for 2 h. Then substituted or unsubstituted 2-aminobenzamide (3.0 mmol) wasadded, and the reaction mixture was stirred at rt for 12 h whilebeing monitored by TLC. After the addition of H2O (10 mL) themixture was extracted with ethyl acetate (3 × 20 mL). Theorganic layers were combined and concentrated under vacuumto give the amide intermediate.
  • 58
  • [ 6089-09-4 ]
  • [ 115643-59-9 ]
  • 2,3-dihydro-1-methylene-8-fluoro-pyrrolo[2,1-b]quinazolin-9(1H)-one [ No CAS ]
  • 59
  • [ 589-18-4 ]
  • [ 115643-59-9 ]
  • 5-fluoro-2-(4-methylphenyl)quinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With potassium hydroxide; In toluene; at 90℃; for 20h; General procedure: To an oven-dried 20 cm3 test tube with a ground-in stopperequipped with a stir bar were added anthranilamide (1.0 mmol), benzyl alcohol (1.0 mmol), KOH (2.0 mmol),and 4 cm3 toluene. The test tube was put in an oil bath potpreheated at 90 C and the mixture was stirred for 20 h at90 C. After cooling to room temperature, the reactionmixture was added about 5 g silica gel and directly condensedon a rotator under vacuum. The resulting residualwas transferred to a silica gel chromatography column andeluted with a solution of petroleum ether and ethyl acetate[4/1 (v/v)] to give a white solid 2-phenyl-4(3H)-quinazolinone.For some products (3f, 3g, 3n, and 3t) onlysparingly soluble in ethyl acetate, the reaction mixtureswere condensed in vacuo on a rotary evaporator. Theresiduals were washed three times with water and oncewith ethyl acetate, and then dried in an infrared oven togive the desired products pure enough for NMR analysis.
  • 60
  • [ 30414-54-1 ]
  • [ 115643-59-9 ]
  • 5-fluoro-2-propylquinazolin-4(3H)-one [ No CAS ]
  • 61
  • [ 115643-59-9 ]
  • [ 2881-83-6 ]
  • 5-fluoro-2-(4-methoxyphenyl)quinazolin-4(3H)-one [ No CAS ]
  • 62
  • [ 123-54-6 ]
  • [ 115643-59-9 ]
  • [ 143745-24-8 ]
YieldReaction ConditionsOperation in experiment
95% With camphor-10-sulfonic acid; In water; at 100℃; for 24h; 2-Amino-6-fluorobenzamide (30.8 mg, 0.2 mmol), Camphorsulfonic acid (4.6 mg, 10 mol%) And 2,4-pentanedione (30.0 mg, 0.3 mmol) were added to 1 ml of a mixed solvent (Vwater: VLactic acid ethyl ester= 9:1) 100 C under reaction 24h, thin layer chromatography to give 2-methyl-5-fluoroquinazolinone 33.8mg, 95% yield, purity 98%
92% With ytterbium(III) triflate; In 1,3,5-trimethyl-benzene; at 60℃; for 24h;Inert atmosphere; General procedure: 2-aminobenzamide (1, 1.0 mmol), 1,3-diketone (2, 1.5 mmol), Yb(OTf)3 (0.050 mmol, 5.0 mol%),and mesitylene (2.0 mL) was placed in a 20-mL Pyrex flask equipped with a magnetic stirring bar and a reflux condenser under a flow of argon. The reaction was carried out at 60C (bath temp.) for 24 h with stirring. The reaction mixture was then cooled to room temperature and analyzed by GLCand GC-MS. The product 3 was isolated by medium-pressure column chromatography on silica gel(eluent: EtOAc/hexane = 30/70 ~ EtOAc 100%. For 3j, eluent: MeOH/CHCl3 = 30/70 ~ 50/50) andrecrystallization from MeOH/hexane. The products 3l and 3m were isolated by recrystallizationfrom EtOAc/hexane. 1H NMR spectra were recorded at 400 MHz, and 13C NMR spectra wererecorded at 100 MHz in DMSO-d6 (For 3j, in a mixture of DMSO-d6 and methanol-d4). Elemental analyses were performed at the Microanalytical Center of Kyoto University. The analytical and spectral data of 3a,10 3b-c,11 3d,12 3e,13 3f,14 3g-h,10 and 3j-l,7 are fully consistent with those reported previously. The products 3i,15 and 3m16 were characterized below.
79% With iron(III) chloride hexahydrate; In water; at 100℃; for 24h;Green chemistry; General procedure: A flask was charged with 2-aminobenzamide (1a; 27.2 mg, 0.2 mmol), pentane-2,4-dione (2A;30.0 mg, 0.3 mmol), FeCl3·6H2O (10.8 mg, 0.04 mmol), and PEG-400/H2O (1.0 mL, 1:9 (v/v)).The reaction was stirred at 100 C for 24 h. When the reaction was complete monitored by TLC,the mixture was cooled to room temperature, extracted with EtOAc (3×20 mL). The combined organic phase was washed with water, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the product 3aA (29.3 mg, 91%) as white solid.
  • 63
  • [ 18362-64-6 ]
  • [ 115643-59-9 ]
  • 5-fluoro-2-(1-methylethyl)quinazolin-4(3H)-one [ No CAS ]
  • 64
  • [ 504-02-9 ]
  • [ 115643-59-9 ]
  • 5-fluoro-2-(4-oxopentyl)quinazolin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With camphor-10-sulfonic acid; In water; ethyl acetate; at 100℃; for 24h; <strong>[115643-59-9]2-amino-6-fluorobenzamide</strong> (30.8 mg, 0.2 mmol)Camphorsulfonic acid (4.6 mg, 10 mol%) and 1,3-cyclohexanedione (33.6 mg, 0.3 mmol) were added to 1 mL of a mixed solvent (V water: v ethyl lactate = 9: 1)At 100 C for 24 h, and purified by thin layer chromatography5-fluoro-2- (4-oxopentyl) quinazolinone49.1 mg, yield 99%, purity 98%.
  • 65
  • [ 115643-59-9 ]
  • [ 869294-95-1 ]
  • 66
  • [ 115643-59-9 ]
  • 6-fluoro-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]
  • 67
  • [ 115643-59-9 ]
  • (E)-3-((dimethylamino)methylene)-6-fluoro-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one [ No CAS ]
  • 68
  • [ 4635-59-0 ]
  • [ 115643-59-9 ]
  • 2-(4-chlorobutanamido)-6-fluorobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With triethylamine; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere; General procedure: Asolutionoftheappropriatesubstituted2-aminobenzamide(1.0eq)inTHF(2.5mLpermmolsubstrate)wascooledto0Candtriethylamine(2.0eq)thentheappropriateacidchloride(1.2eq)inTHF(2mLpermmolsubstrate)wereaddedtothestirredsolution.ThereactionwasstirredatroomtemperatureuntilcompletionasindicatedbyTLC,whenthemixturewasdilutedwithEtOAcandquenchedwithNaHSO4(20mL).TheaqueousphasewasextractedwithEtOAc(320mL),combinedorganicphasesdriedoverMgSO4,excesssolventremovedinvacuoandtheresiduepurifiedbyFCC.
  • 69
  • [ 287917-97-9 ]
  • [ 115643-59-9 ]
  • C11H6BrFN4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium metabisulfite; In N,N-dimethyl acetamide; for 5h;Inert atmosphere; Reflux; Under the argon 2-amino-6-fluoro-benzamide (77 mg, 0 . 50mmol) dissolved in dimethylacetamide (5 ml) in, by adding 4-bromo -1H-pyrazole-5-formaldehyde (88 mg, 0 . 50mmol) and Na 2 S 2 O 5 (143 mg, 0 . 75mmol), and the mixture stirred under the reflow conditions for 5 hours. After the cooling to room temperature, the reaction mixture is concentrated, and dissolved in acetonitrile and N, N-dimethyl formamide in a mixture. Filtered and thoroughly drying the remaining solid, get colorless solid 2 - (4-bromo -1H-pyrazol-5-yl) - 5- [...] -4 (3H)-one (30 mg, of the setpoint value of 19%). 1 HNMR (400MHz, d 6-DMSOdelta, PPM) 13.91 (br.s, 1H, NH), 12.03 (br.s, 1H, NH), 8.22 (s, 1H), 7.80 (dd, 1H), 7.51 (d, 1H), 7.27 (dd, 1H).
  • 70
  • [ 100-52-7 ]
  • [ 115643-59-9 ]
  • [ 1098336-86-7 ]
  • 71
  • [ 6061-04-7 ]
  • [ 115643-59-9 ]
  • 5-fluoro-2-(nitromethyl)quinazolin-4(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In water; at 70℃; for 1.5h; General procedure: 2-Aminobenzamides (1 mmol) and 1,1-dichloro-2-nitroethene (1.2 mmol) were added to 5 mL of water in a 25 mL round-bottom flask. Then stirred at corresponding temperature and corresponding reaction time, after completion, the product precipitated from the reaction mixture and can be easily separated by filtration, then give the pure products.
  • 72
  • [ 119072-55-8 ]
  • [ 115643-59-9 ]
  • 2-(tert-butylamino)-5-fluoroquinazolin-4(3H)-one [ No CAS ]
  • 73
  • [ 171734-72-8 ]
  • [ 115643-59-9 ]
  • 7-fluoro-5,11,12,13-tetrahydro-6H-dibenzo[b,f][1,5]diazonin-6-one [ No CAS ]
  • 74
  • [ 171734-72-8 ]
  • [ 115643-59-9 ]
  • C15H14BrFN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 150℃; for 1h;Inert atmosphere; Microwave irradiation; General procedure: A dry 10 mL microwave flask equipped with a septum inlet and magnetic stirring bar was charged with amine 1a-b/1d-i/4h-i(0.5 mmol), 1-bromo-2-(bromomethyl)benzene (2b, 0.5 mmol) and ACN (2.0 mL) under nitrogen atmosphere. The mixture was then carried out under MW conditions at temperatures as stated in Tables 2 and 3 The reaction was monitored by TLC and LCMS. After completion of step-1, Cs2CO3 (1.5 mmol), CuI (10 mol%) and L-proline (20 mol%) were added and the mixture was continued under MW conditions (pressure 200 psi, power 150 W). The progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was diluted with EtOAc (30 mL)and washed with cold water (2 10 mL). The organic layer was separated, dried over Na2SO4 and purified using flash chromatography to deliver the titled compounds.
  • 75
  • [ 1023284-62-9 ]
  • [ 115643-59-9 ]
  • 2-(3-((4S,4aR,5S,7S,8S,9aS)-4,8-dimethyl-3-oxo-3,4,4a,5,6,7,8,9-octahydro-5,8-epoxy-7,9a-methanobenzo[7]annulen-4-yl)propanamido)-6-fluorobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; General procedure: To a solution of PTMA (1d) (29.0 mg, 0.10 mmol) and aminobenzoates 2 (1.5 mmol or 0.20 mmol) in DMF (1.0 mL) at room temperature were added Et3N or pyridine (0.42 mmol) and HATU(76.1 mg, 0.20 mmol). The mixture was stirred at room temperature overnight and monitored by TLC. Then brine (10 mL) was added.The resulting mixture was extracted with EtOAc (3 5.0 mL), and the combined organic portions were dried over anhydrous sodium sulfate and concentrated in vacuo. compounds 3 were finally prepared through flash column chromatography (eluent: EtOAc/lightpetroleum ether 1:20e5:1).
  • 76
  • [ 100-52-7 ]
  • [ 115643-59-9 ]
  • [ 1571119-70-4 ]
YieldReaction ConditionsOperation in experiment
In water; for 2h;Reflux; 2-Amino-6-fluorobenzamide(154 mg, lmmol), Benzaldehyde (106 mg, lmmol), Water (1 · OmL)And then added to 5mL single-mouth bottle. The mixture was reacted at reflux temperature for 2 hours and then cooled to room temperature. Then join[Cp * Ir (H20) 3] [0Tf] 2 (6.8 mg, 0. ol mmol, 1 mol%) was reacted at reflux temperature for 1 hour and then cooled to room temperatureTheThe solvent was removed under vacuum under reduced pressure and then passed through a column chromatography (developing solvent): Ethyl acetate / n-hexane) to give the pure title compoundObjects,Yield: 84%.
  • 77
  • [ 115643-59-9 ]
  • C16H14FN9O [ No CAS ]
  • 78
  • [ 115643-59-9 ]
  • C16H13FIN9O [ No CAS ]
  • 79
  • [ 115643-59-9 ]
  • C10H6FN3O [ No CAS ]
  • 80
  • [ 434-76-4 ]
  • [ 115643-59-9 ]
YieldReaction ConditionsOperation in experiment
80% With N-hydroxybenzotriazole ammonium salt; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 6h; To a stirred solution of <strong>[434-76-4]2-amino-6-fluoro-benzoic acid</strong> (15 g, 96.77 mmol) in THF (150 mL),EDC.HCl (27 g, 145.16 mmol), HOBt·NH3 (21 g, 145.16 mmol), and DIPEA (52 mL, 290.32mmol) were added at room temperature and stirred for 6 h (TLC indicated completeconversion of compound 1). The reaction mixture was diluted with EtOAc (300 mL) and washed with water (3 x 100 mL), brine (1 x 150 mL). The organic layer was separated, driedover Na2S04, volatiles were evaporated under reduced pressure to afford the crude productwhich was washed with 10% EtOAc-hexanes (2 x 150 mL), dried under high vacuum tofurnish 2-amino-6-fluoro-benzamide ( 12.2 g, 80%) as a pale yellow solid.
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