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[ CAS No. 74733-24-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 74733-24-7
Chemical Structure| 74733-24-7
Chemical Structure| 74733-24-7
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Product Details of [ 74733-24-7 ]

CAS No. :74733-24-7 MDL No. :MFCD17169951
Formula : C10H10O4 Boiling Point : -
Linear Structure Formula :- InChI Key :KCBBJVDPDKULDQ-UHFFFAOYSA-N
M.W : 194.18 Pubchem ID :10631650
Synonyms :

Calculated chemistry of [ 74733-24-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.6
TPSA : 52.6 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.14
Log Po/w (XLOGP3) : 1.79
Log Po/w (WLOGP) : 1.29
Log Po/w (MLOGP) : 1.0
Log Po/w (SILICOS-IT) : 1.9
Consensus Log Po/w : 1.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.22
Solubility : 1.16 mg/ml ; 0.00596 mol/l
Class : Soluble
Log S (Ali) : -2.51
Solubility : 0.596 mg/ml ; 0.00307 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.55
Solubility : 0.542 mg/ml ; 0.00279 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 74733-24-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 74733-24-7 ]

* 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 [ 74733-24-7 ]

[ 74733-24-7 ] Synthesis Path-Downstream   1~64

  • 1
  • [ 68771-39-1 ]
  • [ 74733-24-7 ]
  • [ 188244-70-4 ]
  • 2
  • [ 79236-96-7 ]
  • [ 74733-24-7 ]
YieldReaction ConditionsOperation in experiment
86% With manganese(IV) oxide; In dichloromethane; at 45℃; for 15h; In a 250 m round-bottomed flask, methyl 4-(hydroxymethyl)-3-methoxybenzoate (2.24 g, 11.4 mmol) was combined with dichloromethane (150 ml) to give a colorless solution. Manganese dioxide (7.94 g, 91.3 mmol) was added. The reaction mixture was heated to 45 C and stirred for 15 h. The reaction mixture was filtered through celite and concentrated in vacuum to yield methyl 4-formyl-3-methoxybenzoate as a white solid (1.9 g, 86%); MS (ISN) m/z = 195.1 [(M+H)+].
  • 3
  • [ 74733-24-7 ]
  • [ 103505-61-9 ]
  • [ 188244-63-5 ]
  • 4
  • [ 143-33-9 ]
  • [ 74733-24-7 ]
  • 2-amino-2-(2'-methoxy-4'-methoxycarbonyl)phenylacetonitrile [ No CAS ]
  • 5
  • [ 619-12-5 ]
  • [ 74-88-4 ]
  • [ 74733-24-7 ]
YieldReaction ConditionsOperation in experiment
71.1% With potassium carbonate; In dimethyl sulfoxide; at 25℃; for 4h; Example 23 rel-3-[4-((1S,2S,3R,5S,7S)-5-Hydroxy-adamantan-2-ylcarbamoyl)-2-methoxy-benzyl]-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester A mixture of <strong>[619-12-5]4-formyl-3-hydroxy-benzoic acid</strong> (1 g, 6.01 mmol) in dimethylsulfoxide (10 mL) at 25 C. was treated with potassium carbonate (5.1 g, 37.3 mmol) and methyl iodide (1.3 mL, 20.4 mmol). The reaction was stirred at 25 C. for 4 h. At this time, the reaction was diluted with water (100 mL) and then was extracted into ethyl acetate (3*50 mL). The organics were washed with water (2*100 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford 4-formyl-3-methoxy-benzoic acid methyl ester (830.2 mg, 71.1%) as a light yellow solid. ES+-HRMS m/e calcd for C10H10O4 [M+H+] 195.0652 found 195.0652.
58% With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 3h; To a solution of <strong>[619-12-5]4-formyl-3-hydroxybenzoic acid</strong> (0.5 g, 3.0 mmol) in DMSO (5.2 mL, 0.60 M) was added finely ground potassium carbonate (2.6 g, 19 mmol) and methyl iodide (0.65 mL, 3.0 mmol, 1.0 equiv). The reaction mixture was allowed to stir at rt for 3hrs before being diluted with water and extracted into EtOAc. The organic layer was washed with water (2x), dried over MgSO4, filtered and concentrated in vacuo. The crude product was then purified using flash column chromatography on Si02 (5% MeOH/DCM) to yield a white solid (0.34 g, 58 %).
  • 6
  • [ 109-97-7 ]
  • [ 74733-24-7 ]
  • Tetramethyl 3,3',3",3'"-tetramethoxy-4,4',4",4'"-(21H,23H-porphine-5,10,15,20-tetrayl)tetrabenzoate [ No CAS ]
  • 7
  • [ 399-51-9 ]
  • [ 74733-24-7 ]
  • [ 593267-72-2 ]
  • 8
  • [ 17422-33-2 ]
  • [ 74733-24-7 ]
  • [ 241498-69-1 ]
  • 9
  • [ 267-48-1 ]
  • [ 74733-24-7 ]
  • [ 593267-73-3 ]
  • 10
  • [ 6146-52-7 ]
  • [ 74733-24-7 ]
  • [ 107786-36-7 ]
  • 11
  • [ 86608-70-0 ]
  • [ 74733-24-7 ]
  • 4-((E)-3-[1,3]Dioxolan-2-yl-propenyl)-3-methoxy-benzoic acid methyl ester [ No CAS ]
  • 12
  • [ 74733-24-7 ]
  • [ 80893-99-8 ]
YieldReaction ConditionsOperation in experiment
1.72 g of <strong>[74733-24-7]methyl 4-formyl-3-methoxybenzoate</strong> was dissolved in 8.6 ML of methanol, to which 2.6 ML of a 20% aqueous solution of sodium hydroxide was added at room temperature, and this solution was stirred for one hour at the same temperature.. The reaction mixture, to which water was added, was adjusted to PH 2 with 6M hydrochloric acid, and resultant precipitate was filtered out therefrom and washed with water to yield 1.49 g of 4-formyl-3-methoxybenzoic acid as light yellow solid. NMR(400MHz,DMSO-d6) delta value: 3.99(3H,s), 7.62(1H,d,J=8.0Hz), 7.68(1H,d,J=1.2Hz), 7.79(1H,d,J=8.0Hz), 10.40(1H,s), 13.51(1H,brs)
  • 13
  • [ 74733-24-7 ]
  • [ 667916-16-7 ]
  • 14
  • [ 74733-24-7 ]
  • [ 615581-31-2 ]
  • 15
  • [ 74733-24-7 ]
  • methyl 4-(4-oxopentyl)-3-methoxybenzoate [ No CAS ]
  • 16
  • [ 74733-24-7 ]
  • [ 615581-30-1 ]
  • 17
  • [ 74733-24-7 ]
  • 4-[(1-benzhydryl-6-chloro-1H-indol-3-yl)methyl]-3-methoxybenzoic acid [ No CAS ]
  • 18
  • [ 74733-24-7 ]
  • [ 241498-59-9 ]
  • 19
  • [ 74733-24-7 ]
  • 4-(1-benzhydryl-6-fluoro-1<i>H</i>-indol-3-ylmethyl)-3-methoxy-benzoic acid methyl ester [ No CAS ]
  • 20
  • [ 74733-24-7 ]
  • 4-(1-benzhydryl-6-fluoro-1<i>H</i>-indol-3-ylmethyl)-3-methoxy-benzoic acid [ No CAS ]
  • 21
  • [ 74733-24-7 ]
  • 4-(1-benzhydryl-5-nitro-1<i>H</i>-indol-3-ylmethyl)-3-methoxy-benzoic acid methyl ester [ No CAS ]
  • 22
  • [ 74733-24-7 ]
  • 4-[(1-benzhydryl-5-nitro-1H-indol-3-yl)methyl]3-methoxybenzoic acid [ No CAS ]
  • 23
  • [ 74733-24-7 ]
  • 4-[(5-benzhydryl-5H-[1,3]dioxolo[4,5-f]indol-7-yl)methyl]-3-methoxybenzoic acid [ No CAS ]
  • 24
  • [ 74733-24-7 ]
  • 4-(5-benzhydryl-5<i>H</i>-[1,3]dioxolo[4,5-<i>f</i>]indol-7-ylmethyl)-3-methoxy-benzoic acid methyl ester [ No CAS ]
  • 25
  • [ 74733-24-7 ]
  • 2-amino-(2'-methoxy-4'-carboxy)phenylacetic acid hydrochloride [ No CAS ]
  • 26
  • [ 3556-83-0 ]
  • [ 74733-24-7 ]
YieldReaction ConditionsOperation in experiment
2.50 g of methyl 3-methoxy-4-methylbenzoate was dissolved in 25 ML of benzene, to which 2.72 g of N-bromosuccinimide and 0.23 g of 2,2'-azobisisobutyronitrile were successively added at room temperature, and this solution was stirred for one hour while heating it under reflux.. After 3.90 g of hexamethylenetetramine dissolved in 7.8 ML of acetic acid and 7.8 ML of water was added dropwise to the reaction mixture, benzene was distilled out therefrom, and then the mixture was stirred for one hour while heating it under reflux.. The reaction mixture, which was cooled to room temperature, was added to a mixture of chloroform and water and then adjusted to PH 7 with a 20% aqueous solution of sodium hydroxide, and the organic phase was separated therefrom.. After the resultant organic phase was successively washed with water, a saturated aqueous solution of sodium hydrogen carbonate, and a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure.. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=3:1] to yield 1.74 g of methyl 4-formyl-3-methoxybenzoate as white solid. NMR(400MHz,CDCl3) delta value: 3.96(3H,s), 4.00(3H,s), 7.67(1H,s), 7.68(1H,d,J=7.8Hz), 7.88(1H,d,J=7.8Hz), 10.52(1H,s)
  • 27
  • [ 70264-94-7 ]
  • [ 74733-24-7 ]
YieldReaction ConditionsOperation in experiment
39% With sodium hydrogencarbonate; In dimethyl sulfoxide; at 50℃; for 3h; Reference Example 5; Methyl 4-formyl-3-methoxybenzoate; To a solution of methyl 4-(bromomethyl)-3- methoxybenzoate (3.00 g, 11.6 mmol) in dimethyl sulfoxide (16 ml) was added sodium hydrogen carbonate (1.00 g, 13.6 mmol), and the mixture was stirred at 50C for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous MgS04 and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (1: 0-7:3, v/v) to give the title compound (870 mg, 39%) as a colorless oil. ¹H-NMR (CDCl3) No.: 3.96 (3H, s) , 3. 99 (3H, s) , 7. 67 (lH, s) 7,68 (1H, d, J=8.9 Hz), 7.88 (1H, d, J=8.9 Hz), 10.51 (lH, s).
37% With sodium hydrogencarbonate; In dimethyl sulfoxide; at 50℃; for 3h; To a solution of methyl 4-(bromomethyl)-3-methoxybenzoate (1 .93 mmol, 500 mg) in anhydrous DMSO (2.7 ml_) was added NaHC03 (2.32 mmol, 195 mg). The reaction mixture was stirred for 3 h at 505C. Water was added to the reaction mixture, and the mixture was extracted with EtAcO. The organic layer was dried over anhydrous MgS04, the solvent was filtered and evaporated. The crude product was purified by flash chromatography on silica gel using an elution of 8% ethylacetate in hexanes to give methyl 4-formyl-3-methoxybenzoate (140 mg. Yield: 37%). 1 H NMR (400 MHz, CDCI3) delta 10.51 (1 H, s), 7.87 (1 H, d, J=8.Hz), 7.69-7.67 (2H, m), 4.00 (3H, s), 3.95 (3H, s). LC-MS: tR = 2.75 [M+H]+ = 195 (method 3).
37% With sodium hydrogencarbonate; dimethyl sulfoxide; at 50℃; for 3h; full text is not avalable from article
  • 28
  • [ 74733-24-7 ]
  • [ 188244-67-9 ]
  • 29
  • [ 74733-24-7 ]
  • [ 188244-74-8 ]
  • 30
  • [ 74733-24-7 ]
  • [ 188244-73-7 ]
  • 31
  • [ 74733-24-7 ]
  • [ 188244-66-8 ]
  • 32
  • [ 74733-24-7 ]
  • [ 195433-30-8 ]
  • 33
  • [ 74733-24-7 ]
  • [ 195433-31-9 ]
  • 34
  • [ 74733-24-7 ]
  • [ 195433-24-0 ]
  • 35
  • [ 74733-24-7 ]
  • [ 195433-23-9 ]
  • 36
  • [ 74733-24-7 ]
  • [ 188244-65-7 ]
  • 37
  • [ 74733-24-7 ]
  • [ 188244-71-5 ]
  • 38
  • [ 74733-24-7 ]
  • {2-[2-Methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1-methyl-4-oxo-1,4-dihydro-quinolin-7-yl}-carbamic acid cyclopentyl ester [ No CAS ]
  • 39
  • [ 74733-24-7 ]
  • {2-[2-Methoxy-4-(toluene-2-sulfonylaminocarbonyl)-benzyl]-1-methyl-4-oxo-1,4-dihydro-quinolin-6-yl}-carbamic acid cyclopentyl ester [ No CAS ]
  • 40
  • [ 56256-14-5 ]
  • [ 144-55-8 ]
  • [ 74733-24-7 ]
YieldReaction ConditionsOperation in experiment
79% With dimethyl sulfoxide; at 80℃; for 18h; Example 15 Biphenyl-2-yl-carbamic Acid 1-(2-[4-(4-Carbamoyl-piperidin-1-ylmethyl)-2-methoxybenzoyl]methylamino}ethyl)piperidin-4-yl Ester To a stirred solution of 4-bromo-3-methoxy-benzoic acid (15.0 g, 58 mmol) in DMSO (150 mL) was added NaHCO3 (20.0 g, 230 mmol). This was heated to 80 C. for 18 hours. The reaction was then cooled to room temperature and the solvent removed under reduced pressure. The crude reaction mixture was then dissolved in DCM (200 mL) and washed with 1N HCl (100 mL), water (100 mL), NaCl (sat.) (100 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was sufficiently pure to use without further purification. The product, 4-formyl-3-methoxybenzoic acid methyl ester, was obtained in 79% yield (8.9 g, 45.8 mmol).
  • 41
  • [ 74733-24-7 ]
  • [ 256936-25-1 ]
YieldReaction ConditionsOperation in experiment
47% With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20℃; for 4h; To a stirred solution of <strong>[74733-24-7]4-formyl-3-methoxy-benzoic acid methyl ester</strong> (5.0 g, 26 mmol) in tert-butyl alcohol (200 mL) was added NaH2PO4.2H2O (3.6 g, 26 mmol), water (50 mL), 2-methyl-2-butene (11 mL, 104 mmol), and finally NaClO2 (7.02 g, 78 mmol). The reaction was allowed to stir at room temperature for 4 hours. The solvent was then removed under reduced pressure. The crude reaction mixture was then dissolved in DCM (200 mL) and the product was extracted with 1N NaOH (200 mL). The aqueous layer was washed with DCM (200 mL) and then neutralized with 6N HCl (~40 mL) and the product extracted with DCM (200 mL). The organic layer was then washed with water (100 mL), NaCl (sat.) (100 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was sufficiently pure to use without further purification. The product, 2-methoxyterephthalic acid 4-methyl ester, was obtained in 47% yield (2.4 g, 12.3 mmol).
47% With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20℃; for 4h; To a stirred solution of <strong>[74733-24-7]4-formyl-3-methoxybenzoic acid methyl ester</strong> (5.0 g, 26 mmol; prepared as described in Preparation 17) in tert-butyl alcohol (200 mL) was added NaH2PO4-2H2O (3.6 g, 26 mmol), water (50 mL), 2-methyl-2-butene (11 mL, 104 mmol), and finally NaClO2 (7.02 g, 78 mmol). The reaction was allowed to stir at room temperature for 4 hours. The solvent was then removed under reduced pressure. The crude reaction mixture was then dissolved in DCM (200 mL) and the product was extracted with 1N NaOH (200 mL). The aqueous layer was washed with DCM (200 mL) and then neutralized with 6N HCl (~40 mL) and the product extracted with DCM (200 mL). The organic layer was then washed with water (100 mL), NaCl (sat.) (100 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was sufficiently pure to use without further purification. The title intermediate was obtained in 47% yield (2.4 g, 12.3 mmol).
  • 42
  • [ 74733-24-7 ]
  • [ 210037-76-6 ]
YieldReaction ConditionsOperation in experiment
91% With formic acid; hydroxylamine hydrochloride; at 20 - 50℃; for 25h; Reference Example 51; Methyl 4-cyano-3-methoxybenzoate; To a solution (20 ml) of methyl 4-formyl-3- methoxybenzoate (870 mg, 4.48 mmol) in formic acid was added hydroxylamine hydrochloride (405 mg, 5.82 mmol), and the mixture was stirred at room temperature for 1 hr. The temperature was raised to 50C, and the mixture was further stirred for 24 hrs. Water was added to the reaction mixture, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was dried over anhydrous MgS04, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane- ethyl acetate (1: 0-7:3, v/v) to give the title compound (780 mg, 91%) as a colorless oil. ¹H-NMR (CDCl3) No.: 3.96 (3H, s) , 3. 99 (3H, s) , 7 . 62-7 . 69 (3H, m)
  • 43
  • 5H2 O [ No CAS ]
  • K2 S2 O8 [ No CAS ]
  • [ 3556-83-0 ]
  • [ 74733-24-7 ]
YieldReaction ConditionsOperation in experiment
1.47 g (23%) In water; acetonitrile; 11. Methyl 4-formyl-3-methoxy benzoate (11). To a magnetically stirred solution of 10 (5.87 g, 32.6 mmol) in 1:1 CH3 CN/H2 O (250 mL) was added consecutively CuSO4. 5H2 O (8.13 g, 32.6 mmol) and K2 S2 O8 (26.4 g, 97.7 mmole). The reaction mixture was heated at reflux for 50 minutes then transferred to a separatory funnel and extracted with EtOAc (2*100 mL). The combined organic extracts were dried over Na2 SO4, filtered and evaporated. Purification on silica gel by gravity chromatography (ht of silica gel: 33 cm, diameter: 4 cm, eluent: 5:1 hexanes/EtOAc then 4:1 hexanes/EtOAc) provided 1.47 g (23%) of pure 11.
  • 44
  • [ 56256-14-5 ]
  • [ 67-68-5 ]
  • [ 74733-24-7 ]
YieldReaction ConditionsOperation in experiment
79% With sodium hydrogencarbonate; at 80℃; for 18h; To a stirred solution of 4-bromo-3-methoxybenzoic acid (15.0 g, 58 mmol) in DMSO (150 mL) was added NaHCO3 (20.0 g, 230 mmol). This was heated to 80 C. for 18 hours. The reaction was then cooled to room temperature and the solvent removed under reduced pressure. The crude reaction mixture was then dissolved in DCM (200 mL) and washed with 1N HCl (100 mL), water (100 mL), NaCl (sat.) (100 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was sufficiently pure to use without further purification. The title intermediate was obtained in 79% yield (8.9 g, 45.8 mmol).
  • 45
  • [ 75-16-1 ]
  • [ 74733-24-7 ]
  • [ 1196047-07-0 ]
YieldReaction ConditionsOperation in experiment
Production Example 28; To a mixture of <strong>[74733-24-7]methyl 4-formyl-3-methoxybenzoate</strong> (3.30 g) and THF (30 mL) was added dropwise methyl magnesium bromide (3 M diethyl ether solution, 3.60 mL) under ice-cooling. After dropwise addition, the mixture was stirred for 1 hour under ice-cooling. A saturated aqueous ammonium chloride solution was added thereto to stop the reaction, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, and then dried over an aqueous anhydrous sodium sulfate solution. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain methyl 4-(1-hydroxyethyl)-3-methoxybenzoate (1.92 g).
  • 46
  • [ 74733-24-7 ]
  • [ 1196047-09-2 ]
  • 47
  • [ 74733-24-7 ]
  • [ 1402345-16-7 ]
  • 48
  • [ 74733-24-7 ]
  • [ 1402345-17-8 ]
  • 49
  • [ 74733-24-7 ]
  • [ 1402345-18-9 ]
  • 50
  • [ 74733-24-7 ]
  • [ 1402345-19-0 ]
  • 51
  • [ 1080675-01-9 ]
  • [ 74733-24-7 ]
  • [ 1402345-15-6 ]
YieldReaction ConditionsOperation in experiment
86.8% With sodium methylate; In methanol; at 25℃; for 48h; A mixture of 1-(2-phenylamino-pyridin-3-yl)-ethanone (833 mg, 3.92 mmol) in methanol (16.5 mL) at 25 C. was treated with <strong>[74733-24-7]4-formyl-3-methoxy-benzoic acid methyl ester</strong> (508 mg, 2.61 mmol) and sodium methoxide in methanol (4.37M, 1.2 mL, 5.23 mmol). The reaction was stirred at 25 C. for 48 h. At this time, the reaction was diluted with water (100 mL), neutralized with a 1N aqueous hydrochloric acid solution, and extracted with methylene chloride (3*75 mL). The combined organics were dried over sodium sulfate filtered and concentrated in vacuo. Flash chromatography (40 g silica column, 10-50% ethyl acetate/hexanes) afforded 3-methoxy-4-[(E)-3-oxo-3-(2-phenylamino-pyridin-3-yl)-propenyl]-benzoic acid methyl ester (880 mg, 86.8%) as a red solid. ES+-HRMS m/e calcd for C23H20N2O4 [M+H+] 389.1496 found 389.1494.
  • 52
  • [ 74733-24-7 ]
  • C25H19N2O6(1-)*K(1+) [ No CAS ]
  • 53
  • [ 74733-24-7 ]
  • 3-[4-((1S,2S,3R,5S,7S)-5-hydroxy-adamantan-2-ylcarbamoyl)-2-methoxy-benzyl]-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester [ No CAS ]
  • 54
  • [ 61-54-1 ]
  • [ 20577-61-1 ]
  • [ 74733-24-7 ]
  • [ 1560893-00-6 ]
  • 55
  • [ 571188-59-5 ]
  • [ 68-11-1 ]
  • [ 74733-24-7 ]
  • [ 1402049-25-5 ]
YieldReaction ConditionsOperation in experiment
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; at 0 - 20℃; for 3h; <strong>[74733-24-7]4-formyl-3-methoxy-benzoic acid methyl ester</strong> (1.0 mmol), amine 3 (1.0 mmol), thioglycolic acid (1.0 mmol) were stirred in ethyl acetate, propylphosphonic anhydride (T3P) (1.5 mmol) was added to the reaction mixture at 0 C. The reaction kept for stirring at room temperature for 3 h. After completion of the reaction, the mixture was diluted with water (20 mL) and neutralized by adding 10% NaHCO3 solution. The product was extracted with ethyl acetate (10 mL × 2) and the combined organic layers were washed with water followed by brine solution. The organic phase was dried over anhydrous Na2SO4. The solvent was dried under reduced pressure to afford a desired product as off white solid which was pure enough to perform the next reaction. 1H NMR (400 MHz, DMSO-d6): delta 7.90-7.89 (d, J = 2.4 Hz, 1H, ArH), 7.75-7.72 (m, 2H, ArH), 7.46-7.42 (dd, J = 2.8 Hz, 1H, ArH), 7.34-7.30 (dd, J = 3.2 Hz, 1H, ArH), 6.99-6.97 (d, J = 8.2 Hz, 1H, ArH), 6.72 (s, 1H, thiazolidinone-CH), 3.96-3.90 (m, 2H, thiazolidinone-CH2), 3.71 (s, 3H, OCH3), 3.82 (s, 3H, OCH3), 3.61-3.58 (m, 4H, piperazine-CH2), 3.27-3.25 (m, 4H, piperazine-CH2), 1.51 (s, 9H, t-butyl-CH3).
  • 56
  • [ 150619-47-9 ]
  • [ 74733-24-7 ]
  • [ 1173177-01-9 ]
YieldReaction ConditionsOperation in experiment
62.5% With potassium carbonate; In methanol; at 80℃; for 2h; In a 50 m round-bottomed flask, <strong>[74733-24-7]methyl 4-formyl-3-methoxybenzoate</strong> (1.9 g, 9.78 mmol) was combined with methanol (20 ml) to give a colorless solution. Toluene-4-sulfonylmethyl isocyanide (TOSMIC, 1.91 g, 9.78 mmol) and potassium carbonate (1.35 g, 9.78 mmol) were added. The reaction mixture was heated to 80 C and stirred for 2 h, then cooled to room temperature. Water was added and the reaction mixture was then extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and the solvent was removed under vacuum. The crude material was purified by flash chromatography (silica gel, 40 g, 0% to100% EtOAc in heptane), to yield methyl 3-methoxy-4-(oxazol-5-yl)-benzoate as a white solid(1.43g, 62.5%); MS (ISN) m/z = 233.9 [(M+H)+].
  • 57
  • [ 79236-97-8 ]
  • [ 74733-24-7 ]
  • 58
  • [ 74733-24-7 ]
  • [ 1578190-67-6 ]
  • 59
  • [ 74733-24-7 ]
  • [ 1610874-32-2 ]
  • 60
  • [ 542-92-7 ]
  • [ 106-49-0 ]
  • [ 74733-24-7 ]
  • methyl 4-(3a,4,5,9b-tetrahydro-8-methyl-3H-cyclopenta[c]quinolin-4-yl)-3-methoxybenzoate [ No CAS ]
  • methyl 4-(3a,4,5,9b-tetrahydro-8-methyl-3H-cyclopenta[c]quinolin-4-yl)-3-methoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With scandium tris(trifluoromethanesulfonate); In acetonitrile; at 20℃; for 16h; full text is not avalable from article
  • 61
  • [ 542-92-7 ]
  • [ 104-94-9 ]
  • [ 74733-24-7 ]
  • endo-methyl 4-(3a,4,5,9b-tetrahydro-8-methoxy-3H-cyclopenta[c]quinolin-4-yl)-3-methoxybenzoate [ No CAS ]
  • exo-methyl 4-(3a,4,5,9b-tetrahydro-8-methoxy-3H-cyclopenta[c]quinolin-4-yl)-3-methoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With scandium tris(trifluoromethanesulfonate); In acetonitrile; at 20℃; for 16h; full text is not avalable from article
  • 62
  • [ 24589-98-8 ]
  • [ 74-88-4 ]
  • [ 74733-24-7 ]
  • 63
  • [ 2301-80-6 ]
  • [ 74733-24-7 ]
  • C17H18NO3(1+)*I(1-) [ No CAS ]
  • 64
  • [ 74733-24-7 ]
  • [ 102362-00-5 ]
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