Structure of 22312-62-5
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CAS No. : | 22312-62-5 |
Formula : | C14H14N2O |
M.W : | 226.27 |
SMILES Code : | O=C(NC1=CC=CC(C)=C1)C2=CC=CC=C2N |
MDL No. : | MFCD00442835 |
InChI Key : | ZLUXETNDOIBMSR-UHFFFAOYSA-N |
Pubchem ID : | 2467368 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene; at 100℃; for 12h; | General procedure: 7.1.13. Solution-phase synthesis of library compounds 21Isatoic anhydride (20) (0.1 mmol) was partitioned into reaction vials and treated with aniline (0.10 mmol) in toluene (1.0 mL) at 100 C for 12 h. The mixture in each vessel was allowed to coolto ambient temperature, and the solvent was removed under reduced pressure. The residue in each vessel was dissolved in pyridine(1.0 mL) and treated with compound 37 (0.10 mol) at ambient temperature for 12 h. The mixture was then treated with polymer-bound tris(2-aminoethyl)amine for 12 h and filtered off. The filtrate was collected in vials and the solutions were evaporatedin vacuo to afford anthranilamide derivatives 21, which were analyzed by HPLC and MS. 21a; FAB-MS m/z 443 [M+H]+, 21b; FABMS m/z 443 [M+H]+, 21c; FAB-MS m/z 443 [M+H]+, 21d; FAB-MS m/z 463 [M+H]+, 21e; FAB-MS m/z 463 [M+H]+, 21g; FAB-MS m/z459 [M+H]+, 21h; FAB-MS m/z 489 [M+H]+, 21i; FAB-MS m/z 493[M+H]+, 21j; FAB-MS m/z 513 [M+H]+, 21k; FAB-MS m/z 521[M+H]+, 21l; FAB-MS m/z 472 [M+H]+, 21m; FAB-MS m/z 457 [M+H]+, 21n; FAB-MS m/z 471 [M+H]+, 21o; FAB-MS m/z 430[M+H]+, 21p; FAB-MS m/z 444 [M+H]+, 21q; FAB-MS m/z 444[M+H]+, 21r; FAB-MS m/z 444 [M+H]+, 21s; FAB-MS m/z 460 [M+H]+, 21t; FAB-MS m/z 449 [M]+, 21u; FAB-MS m/z 433[M+H]+, 21v; FAB-MS m/z 469 [M+H]+, 21w; FAB-MS m/z 480[M+H]+. Compound 21f was obtained from 2-amino-5-chloro-3-hydroxy-40-methoxybenzanilide using the methods described forthe synthesis of compound 19 as a colorless solid (423 mg, 56%): | |
With ethyl acetate; at 70℃; for 24h; | General procedure: A flame-dried 25 mL reaction tube was placed with a stirring bar. Then, Nmethylisatoicanhydride (2 mmol), amine compounds (1.0 equiv) and EtOAc (4.0 mL)were added. The resulting mixture was stirred at 70 for 24 hours. Then, the reactionmixture was concentrated and purified by column chromatography (silica gel) to givethe target product A. A flame-dried 100 mL round-bottom flask was placed with a stirring bar. Then, A (1.5 mol), R2B(OH)2 (1.5 equiv), CuCl (20 mol%), Et3N (50 mol%) and MeOH (30 mL)were added, The resulting mixture was stirred at room temperature for 12 hours. Then,the reaction mixture was filtered, concentrated, and purified by columnchromatography (silica gel) to give the target product B. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With tert.-butylnitrite; tetra-(n-butyl)ammonium iodide; In acetonitrile; at 60℃; for 12h;Sealed tube; | General procedure: 2-aminobenzamides (1a-z, 0.2 mmol), TBAI (3.7 mg, 0.01 mol), tert-butylnitrite (72 μL, 0.6 mmol) and CH3CN (2.0 mL) were successively addedto a 10 mL of sealed tube. The mixture was stirred at 60 C for 12 h at air. The solution was then cooled to r.t. and evaporated undervaccum. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 6:1 to 3:1) to afford the desired products3a-z. |
82% | With tert.-butylnitrite; tetra-(n-butyl)ammonium iodide; In acetonitrile; at 60℃; for 12h;Green chemistry; | The reaction flask was added with 1c (2mmol, 452mg), and added tert-butyl nitrite (6mmol, 0.72mL), followed by tetrabutylammonium iodide (5mol%,37 mg ) and acetonitrile (20mL). Then the system was heated for 12 hours at 60 deg C. air, vacuum spin dry acetateAfter the nitrile with petroleum ether / ethyl acetate = 6/1 mixed solvent of a simple column chromatography to give the product 2c, yield 82%. yellowSolid color |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iron; ammonium chloride; In ethanol; water; at 90℃; for 3h; | General procedure: Compound c (15 mmol), reductive iron powder (15 mmol),NH4Cl (45 mmol), and ethanol aqueoussolution (75%, 60 mL) were added in a flask. The reaction proceeded with refluxing for 3 h, at 90 C.When the reaction finished, the mixtures were cooled to room temperature and extracted with CH2Cl2(3 x 20 mL) and the organic phase was evaporated in a vacuum to obtain compound d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(2ac) 2-Amino-N-(3-methylphenyl)benzamide, m.p. 115-117 C., utilizing 3-methylaniline; (2ad) 2-Amino-N-(3-benzoylphenyl)benzamide, as a yellow oil, utilizing (3-aminophenyl)phenylmethanone; (2ae) 2-Amino-N-[(3-aminocarbonyl)phenyl]benzamide, utilizing 3-aminobenzamide. Intermediate 2af: 2-Amino-N-(4-methylphenyl)-6-methylbenzamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1,2-dichloro-ethane; triethylamine; In N,N-dimethyl-formamide; | Step 1: Preparation of 2-amino-N-(3-methylphenyl)benzamide (64) To a solution of 2-aminobenzoic acid (290 mg) and 3-methylaniline (215 mg) in 10 mL of DMF was added 1-hydroxybenzotriazole (300 mg), EDC (400 mg) and triethylamine (500 μL). The resulting solution was stirred for 16 h. The reaction solution was partitioned with ethyl acetate and water. The ethyl acetate layer was extracted w/50 mL each of 5% citric acid, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation of 2-[2(R)-Amino-3-mercaptopropylamino]-N-(3-methylphenyl)-benzamide trifluoroacetate (65) The title compound was prepared from 64 using the method described in Steps 3 and 4 of Example 1, except that the ion exchange with BioRad AG 3-X4 was omitted. Analysis Calculated for C17 H21 N3 OS·1.15 TFA·0.3 H2 O: C, 51.28; H, 5.07; N, 9.30; Found: C, 51.29; H, 5.04; N, 9.29. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | for 5h;Heating / reflux; | A mixture of commercially available 49 (2 g, 0.009 mol) and 1,1,1-triethoxy-ethane (5.2 mL, 0.028 mol) were heated for 5 hours. The reaction mixture was poured into water, washed with water yielding 50 (70%). After recrystallization from EtOH the crude material was used in next step without further purification. |
for 5h;Heating; | 2-Methyl-3-m-tolyl-3H-quinazolin-4-one (50): A mixture of commercially available 49 (2 g, 0.009 mol) and 1,1,1-triethoxy-ethane (5.2 mL, 0.028 mol) were heated for 5 hours. The reaction mixture was poured into water, washed with water yielding 50 (70%). After recrystallization from EtOH the crude material was used in next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: 7.1.13. Solution-phase synthesis of library compounds 21Isatoic anhydride (20) (0.1 mmol) was partitioned into reaction vials and treated with aniline (0.10 mmol) in toluene (1.0 mL) at 100 C for 12 h. The mixture in each vessel was allowed to coolto ambient temperature, and the solvent was removed under reduced pressure. The residue in each vessel was dissolved in pyridine(1.0 mL) and treated with compound 37 (0.10 mol) at ambient temperature for 12 h. The mixture was then treated with polymer-bound tris(2-aminoethyl)amine for 12 h and filtered off. The filtrate was collected in vials and the solutions were evaporatedin vacuo to afford anthranilamide derivatives 21, which were analyzed by HPLC and MS. 21a; FAB-MS m/z 443 [M+H]+, 21b; FABMS m/z 443 [M+H]+, 21c; FAB-MS m/z 443 [M+H]+, 21d; FAB-MS m/z 463 [M+H]+, 21e; FAB-MS m/z 463 [M+H]+, 21g; FAB-MS m/z459 [M+H]+, 21h; FAB-MS m/z 489 [M+H]+, 21i; FAB-MS m/z 493[M+H]+, 21j; FAB-MS m/z 513 [M+H]+, 21k; FAB-MS m/z 521[M+H]+, 21l; FAB-MS m/z 472 [M+H]+, 21m; FAB-MS m/z 457 [M+H]+, 21n; FAB-MS m/z 471 [M+H]+, 21o; FAB-MS m/z 430[M+H]+, 21p; FAB-MS m/z 444 [M+H]+, 21q; FAB-MS m/z 444[M+H]+, 21r; FAB-MS m/z 444 [M+H]+, 21s; FAB-MS m/z 460 [M+H]+, 21t; FAB-MS m/z 449 [M]+, 21u; FAB-MS m/z 433[M+H]+, 21v; FAB-MS m/z 469 [M+H]+, 21w; FAB-MS m/z 480[M+H]+. Compound 21f was obtained from 2-amino-5-chloro-3-hydroxy-40-methoxybenzanilide using the methods described forthe synthesis of compound 19 as a colorless solid (423 mg, 56%): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With choline chloride; toluene-4-sulfonic acid; at 20℃; for 1h;Green chemistry; | General procedure: To a mixture of 2-formylbenzoic acid (1; 1 mmol) and the appropriate amine 2, 4, or 6 (1 mmol) was added the DES (1.5 g), prepared from ChCl and TsOH.31 The resulting mixture was stirred at r.t. until the starting materials were completely consumed (TLC). The reaction mass was then diluted with H2O (5mL), and the desired product, obtained as a precipitate, was isolated by filtration and crystallized from the appropriate solvent.The filtrate was evaporated under vacuum at 70 C for 2 h, and the residual DES was reused in further reaction cycles. |
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