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[ CAS No. 69454-42-8 ] {[proInfo.proName]}

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Chemical Structure| 69454-42-8
Chemical Structure| 69454-42-8
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Product Details of [ 69454-42-8 ]

CAS No. :69454-42-8 MDL No. :MFCD10655727
Formula : C11H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :DPYAPCOWWDVERX-UHFFFAOYSA-N
M.W : 203.19 Pubchem ID :641183
Synonyms :

Calculated chemistry of [ 69454-42-8 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.09
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.85
TPSA : 59.16 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) : -6.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.01
Log Po/w (XLOGP3) : 1.4
Log Po/w (WLOGP) : 1.31
Log Po/w (MLOGP) : 1.51
Log Po/w (SILICOS-IT) : 2.43
Consensus Log Po/w : 1.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.34
Solubility : 0.922 mg/ml ; 0.00454 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 1.15 mg/ml ; 0.00567 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.69
Solubility : 0.0415 mg/ml ; 0.000204 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 69454-42-8 ]

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

Application In Synthesis of [ 69454-42-8 ]

* 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 [ 69454-42-8 ]

[ 69454-42-8 ] Synthesis Path-Downstream   1~77

  • 1
  • methyl 2-azido-3-(o-formylphenyl)propenoate [ No CAS ]
  • [ 69454-42-8 ]
  • 2
  • methyl 2-azido-3-(o-formylphenyl)propenoate [ No CAS ]
  • [ 69454-42-8 ]
  • [ 111686-57-8 ]
  • 3
  • methyl 2-azido-3-<o-(1,3-dioxolan-2-yl)phenyl>propenoate [ No CAS ]
  • [ 69454-42-8 ]
  • methyl 2-azido-3-(o-formylphenyl)propenoate [ No CAS ]
  • 4
  • [ 77-78-1 ]
  • 3-carboxy-1(2H)-isoquinoline [ No CAS ]
  • [ 69454-42-8 ]
  • 5
  • [ 4122-56-9 ]
  • [ 89524-99-2 ]
  • [ 69454-42-8 ]
  • 7
  • [ 69454-42-8 ]
  • [ 349552-70-1 ]
YieldReaction ConditionsOperation in experiment
90% With trichlorophosphate; In methanol; at 130℃; for 0.166667h;Microwave irradiation; A mixture of 30 (594 mg, 2.92 mmol) and POCl3 (3 ml, 32.8 mmol) was heated 10 min at 130 C using Biotage Initiator microwave synthesizer. The resulting reaction mixture was dissolved in ethyl acetate (100 ml) and washed with HCl (1 M, 3× 100 ml). The organic phase was dried (Na2SO4) and evaporated to dryness. The crude product was purified by flash chromatography (silica gel) eluting with EtOAc/PE 1:3 to give 31 (585 mg, 90%). 1H NMR (DMSO-d6): delta 8.59 (s, 1H); 8.27 (d, 1H, 3JHH = 8.1 Hz); 8.23 (d, 1H, 3JHH = 7.3 Hz); 7.94 (m, 2H); 3.99 (s, 3H). 13C NMR (DMSO-d6): delta 163.9; 150.1; 139.3; 136.6; 132.0; 131.2; 128.7; 127.1; 125.4; 124.0; 52.2.
87% With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene; for 5h;Reflux; The mixture of 35 (190 mg, 0.94 mmol),POCl3 (94 muL, 1.03 mmol) and DIPEA (360 muL, 2.07 mmol) in toluene (8 mL) was refluxed for5 h. After cooled down, the mixture was diluted with EtOAc (15 mL) and washed with ice-coldwater, saturated NaHCO3, brine. The organic layer was dried over Na2SO4. The solvent wasremoved under reduced pressure and the residue was purified by silica gel to give 138 mg whitesolid, in 87% yield. 1H NMR (400 MHz, CDCl3) 8.54 (s, 1H), 8.43 (m, 1H), 8.02 (m, 1H),7.887.82 (m, 2H), 4.05 (s, 3H).
87% With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene; for 5h;Reflux; Themixture of 42 (190 mg, 0.94mmol), POCl3 (94 muL, 1.03 mmol) and DIPEA (360 muL, 2.07 mmol) intoluene (8 mL) was refluxed for 5 h. After cooled down, the mixture was dilutedwith EtOAc (15 mL) and washed with ice-cold water, saturated NaHCO3,brine. The organic layer was dried over Na2SO4. Thesolvent was removed under reduced pressure and the residue was purified bysilica gel to give 138 mg white solid, in 87% yield. 1H NMR (400MHz, CDCl3) d 8.54(s, 1H), 8.43 (m, 1H), 8.02 (m, 1H), 7.88-7.82(m, 2H), 4.05 (s, 3H)
64% Synthesis of methyl 4-chloroisoquinoline-2-carboxylate: Methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate (0.68g, 3.3mmoles) was dissolved in excess phosphorus oxy chloride (5 mis) and the clear solution heated (950C) for 3 hours and overnight at room temperature. The reaction was diluted with toluene (10mIs) and azeotroped twice. The residual oil was diluted with dichloromethane (10mls) and quenched with ice cooled water (50mIs). Further dichloromethane was added (15mls) and the layers separated. The aqueous layer was extracted with dichloromethane (10mIs) and the dichloromethane phases combined and washed with saturated sodium bicarbonate (10mIs), water (10mIs) and brine (10mIs). After drying over magnesium sulphate the solution was filtered and concentrated to give an off white solid. (0.47g, 64% yield).

  • 8
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  • 10
  • [ 67-56-1 ]
  • [ 610-94-6 ]
  • immobilized on REM resin N-acetyldehydroalanine [ No CAS ]
  • [ 69454-42-8 ]
  • 11
  • [ 35356-70-8 ]
  • [ 610-97-9 ]
  • [ 69454-42-8 ]
YieldReaction ConditionsOperation in experiment
72% With sodium hydrogencarbonate;tetrabutyl-ammonium chloride; palladium diacetate; In N,N-dimethyl-formamide; at 55℃; for 15h; Example 1Preparation of (4-fluorophenyl)Q-(5-methyl-lH-pyrazol-3-ylamino)isoquinolin-3-yl)methanone[00225] Step A: To a stirred mixture of methyl 2-iodobenzoate (1.46 g, 5.57 mmol), palladium (0) acetate (25 mg, 0.11 mmol), tetrabutylammonium chloride (1.54 g, 5.57 mmol) and sodium hydrogen carbonate (1.17 g, 13.92 mmol) in N, N- dimethylformamide (11 mL) was added methyl 2-acetamidoacrylate (1.19g, 8.35 mmol), and the mixture was heated at 55 C for 15 h. After cooling to rt, the mixture was partitioned between water and EtOAc, and then the separated aqueous layer was extracted three times with EtOAc. The combined organic layers were dried over Na2S04, filtered, and concentrated under reduced pressure. The residue was recrystallized from EtOAc to afford methyl l-oxo-l,2-dihydroisoquinoline-3- carboxylate as a colorless solid (820 mg, 72%). JH NMR (400 MHz, DMSO-d6) delta 11.21 (s, 1H), 8.26 (d, J= 8.0 Hz, 1H), 7.92 (d, J= 7.6 Hz, 1H), 7.79-7.83 (m, 1H), 7.65-7.69 (m, 1H), 7.46 (s, 1H), 3.90 (s, 3H); LC-MS (ESI) m/z 204 (M+H)+.
  • 12
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  • [ 124-41-4 ]
  • [ 69454-42-8 ]
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  • [ 69454-42-8 ]
  • [ 439614-62-7 ]
  • 14
  • [ 69454-42-8 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 82 percent / POBr3; K2CO3 / acetonitrile / 1.5 h / Heating 2: 90 percent / K2PO4 / Pd(PPh3)4 / dimethylformamide / 5 h / 80 °C 3: 95 percent / NaOH / aq. ethanol / 1 h / Heating
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  • [ 349552-76-7 ]
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  • [ 349552-77-8 ]
  • 19
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  • [ 349552-75-6 ]
  • 20
  • [ 69454-42-8 ]
  • (+)-3-bromomethyl-1-(2-hydroxy-1-naphthyl)isoquinoline [ No CAS ]
  • 21
  • [ 69454-42-8 ]
  • [ 349552-73-4 ]
  • 22
  • [ 69454-42-8 ]
  • [ 349552-72-3 ]
  • 23
  • [ 69454-42-8 ]
  • [ 349552-71-2 ]
  • 24
  • [ 69454-42-8 ]
  • (+)-3-bromomethyl-1-(3,6-di-tert-butyl-2-hydroxy-1-naphthyl)isoquinoline [ No CAS ]
  • 25
  • [ 69454-42-8 ]
  • bis[3-(1-(2-hydroxy-1-naphthyl)isoquinolyl)methyl]sulphide [ No CAS ]
  • 26
  • [ 69454-42-8 ]
  • bis[3-(1-(3,6-di-tert-butyl-2-hydroxy-1-naphthyl)isoquinolyl)methyl]sulphide [ No CAS ]
  • 27
  • [ 119-67-5 ]
  • [ 69454-42-8 ]
  • 31
  • [ 69454-42-8 ]
  • 3-Carbomethoxy-N-(3,4-dimethoxybenzenesulphonyl)-1-oxo-1,2-dihydroisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 18 3-Carbomethoxy-N-(3,4-dimethoxybenzenesulphonyl)-1-oxo-1,2-dihydroisoquinoline. Prepared from <strong>[69454-42-8]3-carbomethoxy-1-oxo-1,2-dihydroisoquinoline</strong> (J. Org. Chem., 1979,44, 1887-1888). Purification by column chromatography afforded an off-white solid (0.13 g). TLC Rf 0.4 (50% ethyl acetate/hexane). mp 160-162 C.
  • 32
  • [ 100-39-0 ]
  • [ 69454-42-8 ]
  • [ 945771-34-6 ]
YieldReaction ConditionsOperation in experiment
96% With silver carbonate; In toluene; at 100℃; for 2h;Inert atmosphere; To a stirred solution of compound 3 (300 mg, 1.48 mmol) in toluene (10 mL) at RT and under an inert atmosphere, were added benzyl bromide (0.21 mL, 1.77 mmol) and Ag2C03 (611 mg, 2.22 mmol). The reaction mixture was heated at 100 C for 2 h. The reaction mixture was filtered through a pad of celite (to remove solid impurities) then the filtrate was concentrated under reduced pressure. The residue was purified (silica gel; eluting with 15% EtOAc in hexanes) to afford compound 4 (420 mg, 96%) as pale yellow viscous liquid. 1H NMR (500 MHz, CDC13): delta 8.35 (d, J= 8.1 Hz, 1H), 8.20 (s, 1H), 7.88 (d, J= 8.1 Hz, 1H), 7.74 (t, J= 6.9 Hz, 1H), 7.67 (t, J= 7.2 Hz, 1H), 7.60 (d, J= 7.2 Hz, 2H), 7.42 (t, J= 6.9 Hz, 2H), 7.36 (m, 1H), 5.69 (s, 2H), 4.03 (s, 3H); LCMS Mass: 293.9 (M++l).
With silver carbonate; In toluene; at 100℃; for 2h; (4) The mixture of methyl l-oxo-l,2-dihydroisoquinoline-3-carboxylate (15.3g), benzyl bromide (10.75ml), silver carbonate (3Ig) and toluene (300ml) is stirred at 100C for 2 hours. The insoluble materials are removed by filtration through Celite, and the filtrate is concentrated under reduced pressure. Crystallization of the residue from diisopropylether gives methyl l-benzyloxy-isoquinoline-3-carboxylate (21.3g). MS (m/z): 294 [M+H]+
  • 33
  • [ 67-56-1 ]
  • [ 7509-13-9 ]
  • [ 69454-42-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid;Heating / reflux; (3) The mixture of l-oxo-l^-dihydroisoquinoline-S-carboxylic acid (19.Og), a concentrated sulfuric acid (100ml) and methanol (500ml) is heated under reflux overnight. The reaction solution is poured into ice- water and the mixture is extracted with chloroform. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The precipitated crystals are filtered with diisopropylether to give methyl l-oxo-l,2-dihydroisoquinoline- 3-carboxylate (15.4g). MS (m/z): 204 [M+H]+
  • 34
  • [ 23364-15-0 ]
  • [ 69454-42-8 ]
YieldReaction ConditionsOperation in experiment
22% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane;Reflux; Synthesis of Starting Material 1:; DDQ/1 ,4-dioxane reflux To a solution of compound 1-Oxo-l, 2, 3, 4-tetrahydroisoquinoline 3- carboxymethyl ester (13.6 Ig; 66 mmol) in 200 rnL of 1 ,4-dioxane was added 2,3- dichloro-5,6-dicyanobenzoquinone (DDQ) (16.Og; 70.5 mmol). The resultant mixture was refluxed overnight. After the reaction was complete, the solvent was removed. The residue was taken up with 200 mL ethyl acetate and washed with 5% NaOH (2x50mL). The organic layer was dried over anhydrous sodium sulfate. The drying agent was filtered and the filtrate was evaporated. The crude product was purified with flash chromatography (silica gel/ ethyl acetate/ hexanes) to give the product (starting material 1) as a white solid (3.0 g; 22%), mp 154-155 0C. 1H NMR (CDCl3): 3.92 (s, 3H), 7.52-7.68 (m, 4H), 8.37-8.41 (m, IH), 9.12 (s, IH).
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YieldReaction ConditionsOperation in experiment
Synthesis of Compounds V-14 and V-15:; To a solution of starting material 1 (5 mmol) in 10 mL dioxane was added IM lithium hydroxide (10 mL), and the reaction mixture was stirred at room temperature for 1 h. The solvent was removed on the rotary evaporator and the residue was treated with 20 mL water and acidified to pH 2, forming a precipitate. The precipitate was collected by suction filtration and washed with 20 mL ethyl acetate to give the corresponding acid as a white solid (80% yield), mp 230-232 0C. 1H NMR (DMSO- 5 D6): 7.40 (s, IH), 7.60-7.68 (t, IH), 7.75-7.83 (t, IH), 7.83-7.88 (d, IH), 8.20-8.25 (d, 1 H), 11.80 (s, IH). A solution of the acid (2 mmol) in dry N, N- dimethylformamide (DMF) (5 mL) was treated with l-[3-(dimethylamino)propyl]- 3-ethylcarbodiimide hydrochloride (EDCI) (0.38 g; 2 mmol), followed by 2 mmol of amine RNH2 (R is D4 for Compound V-14; R is D5 for Compound V-15). The10 reaction mixture was stirred at room temperature overnight. The solvent was removed under vacuum and to the residue was added ethyl acetate (30 mL). The organic layer was washed with 5% aqueous HCl (3 x 10 mL), saturated aqueous NaHCO3 (3 x 10 mL), and brine (10 mL). The organic layer was dried over anhydrous sodium sulfate. The drying agent was filtered and the solvent was removed. The15 crude product was purified by flash chromatography (silica gel/ ethyl acetate/ hexanes) to give the product.Compound V-14: white solid (15% yield), mp 189-191 0C. 1H NMR (CDCl3) 4.68- 4.73 (d, 2H), 7.20-8.08 (m, 10H), 10.88 (s, IH).Compound V-15: white solid (10% yield), mp 138-140 0C. 1H NMR (DMSO-D6) 20 4.48 (s, 2H), 6.34-6.36 (m, IH), 6.60-6.62 (m, IH), 7.35 (s, IH), 7.57-7.80 (m, 4H), 8.20-8.24 (d, IH).
803 mg With water; sodium hydroxide; In tetrahydrofuran; methanol; at 10 - 35℃; for 12h; Reference Example 99 1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid To a mixed solution of <strong>[69454-42-8]methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate</strong> (914 mg, synthesized by a method described in Tetrahedron Lett., 1999, 40, 7935) in THF (10 ml)-methanol (10 ml) was added 1N aqueous sodium hydroxide solution (10 ml), and the mixture was stirred at room temperature for 12 hrs. The reaction mixture was acidified with 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The obtained crude crystals were washed with diisopropy ether to give the title compound (803 mg). 1HNMR (CDCl3) delta: 7.40 (1H, s), 7.59-7.69 (1H, m), 7.79 (1H, dt, J=1.4 Hz, 7.5 Hz), 7.88 (1H, d, J=7.0 Hz), 8.25 (1H, d, J=7.6 Hz), 10.90 (1H, br a).
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YieldReaction ConditionsOperation in experiment
99% With potassium hydroxide; In methanol; at 65℃; for 1h; Synthesis of methyl 1-oxo-1,2-dihydroisoquinoline-3-carboxylate: The 2-carboxymethylbenzaldehyde hippuric acid adduct from above (1.0g, 3.3mmoles) was dissolved in methanol (20mIs) and solid potassium hydroxide (0.37g, 6.6mmoles) was added. The clear solution was heated (65C) for 1 hour. The reaction was evaporated and the solid residue partitioned between water (25mls) and ethyl acetate (25mls). The aqueous layer was further extracted with ethyl acetate (2x10mIs) and the combined ethyl acetate extracts washed with brine (10mls) water (10mls). After drying over magnesium sulphate the solution was evaporated to leave a yellow solid (0.68g, 99% yield).
87% To the suspension of 34 (5.064g, 16.48 mmol) in MeOH (50 mL) was added KOH (85% pellets, 5.634 g, 85.36 mmol). Theresultant mixture was refluxed for 2 h. After cooled down, water (30 mL) was added and themixture was neutralized with 1 N HCl, and extracted with EtOAc (45 mL 2). The combinedorganic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure. To theresidue was added 1 N HCl (25 mL), and the mixture was then heated at 100 C for several23minutes. The precipitate was collected by filtration, washed with water and dried to give 2.899 gwhite solid, in 87% yield. 1H NMR (400 MHz, CDCl3) 9.06 (brs, 1H, exchangeable), 8.46 (dd,J = 0.42 Hz, 7.98 Hz, 1H), 7.767.61 (m, 3H), 7.37 (s, 1H), 3.99 (s, 3H).
87% To the suspension of 41 (5.064 g, 16.48 mmol) in MeOH (50 mL) was added KOH (85%pellets, 5.634 g, 85.36 mmol). The resultant mixture was refluxed for 2 h.After cooled down, water (30 mL) was added and the mixture was neutralized with1 N HCl, and extracted with EtOAc (45 mL 2). The combined organic phases were dried over Na2SO4,filtered, and concentrated under reduced pressure. To the residue was added 1 NHCl (25 mL), and the mixture was then heated at 100 C forseveral minutes. The precipitate was collected by filtration, washed with waterand dried to give 2.899 g white solid, in 87% yield. 1H NMR (400MHz, CDCl3) d 9.06(brs, 1H, exchangeable), 8.46 (dd, J = 0.42 Hz, 7.98 Hz, 1H),7.76-7.61 (m, 3H), 7.37 (s, 1H),3.99 (s, 3H)
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YieldReaction ConditionsOperation in experiment
1.53 g With potassium hydroxide; In methanol; at 100℃; for 0.416667h;Microwave irradiation; A mixture of the crude 29 (3.05 g, 9.92 mmol) from the previous step, KOH (1.11 g, 19.8 mmol) and MeOH (10 ml) was heated 25 min at 100 C using Biotage Initiator microwave synthesizer. The resulting reaction mixture was dissolved in ethyl acetate (100 ml) and washed with saturated Na2CO3 (2× 100 ml) and H2O (2× 100 ml). The organic phase was dried (Na2SO4) and evaporated to dryness. The crude product was purified by flash chromatography (silica gel) eluting with EtOAc/PE 1:5 to 1:1 to give 30 (1.53 g, 76% calculated from 28). 1H NMR (DMSO-d6): delta 10.70 (s, 1H); 8.25 (d, 1H, 3JHH = 8.0 Hz); 7.80-7.68 (m, 2H), 7.54 (t, 1H, 3JHH = 8.1 Hz); 6.82 (s, 1H), 3.20 (s, 3H). 13C NMR (DMSO-d6): delta 162.5; 136.8; 135.3; 132.94; 127.5; 127.4; 127.1; 126.5; 112.4; 105.7; 49.9.
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  • [ 1268691-06-0 ]
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  • 41
  • [ 69454-42-8 ]
  • [ 1268691-09-3 ]
  • 42
  • [ 61650-22-4 ]
  • [ 922-67-8 ]
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  • 44
  • [ 64-17-5 ]
  • [ 69454-42-8 ]
  • [ 94726-24-6 ]
YieldReaction ConditionsOperation in experiment
83% Step B: A mixture of methyl l-oxo-l,2-dihydroisoquinoline-3-carboxylate (2.03 g, 10 mmol) and IN HCl/EtOH (20 mL) was stirred at 100 C for 3 h. The mixture was cooled to rt, concentrated under reduced pressure, and adjusted to pH 7 with aq sodium hydrogen carbonate. The mixture was then extracted with EtOAc and the combined organic layers were dried over Na2S04j filtered, and concentrated under reduced pressure to afford ethyl l-oxo-l,2-dihydroisoquinoline-3-carboxylate as a tan solid (1.8 g, 83%). 1H NMR (400 MHz, DMSO-d6) delta 11.19 (s, 1H), 8.26 (d, J= 8.0Hz, 1H), 7.92 (d, J= 8.0 Hz, 1H), 7.79-7.73 (m, 1H), 7.66-7.68 (m, 1H), 7.44 (s, 1H), 4.36 (q, J= 7.2 Hz, 2H), 1.36 (t, J= 7.2 Hz, 3H); LC-MS (ESI) m/z 218 (M+H)+
  • 45
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  • [ 1256353-08-8 ]
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  • [ 1362689-45-9 ]
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  • [ 1362689-16-4 ]
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  • [ 1362689-15-3 ]
  • 57
  • [ 69454-42-8 ]
  • 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(1-methylisoquinolin-3-carboxamido)morphinan hydrochloride [ No CAS ]
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  • 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(1-cyanoisoquinoline-3-carboxamido)morphinan hydrochloride [ No CAS ]
  • 60
  • [ 69454-42-8 ]
  • 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(1-chloroisoquinoline-3-carboxamido)morphinan hydrochloride [ No CAS ]
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  • 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(1-cyanoisoquinoline-3-carboxamido)morphinan hydrochloride [ No CAS ]
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  • 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-(1-methylisoquinolin-3-carboxamido)morphinan hydrochloride [ No CAS ]
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  • N-[3-(methyloxy)phenyl]methyl}-1-oxo-1,2-dihydroisoquinoline-3-carboxamide [ No CAS ]
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  • [ 1220959-04-5 ]
  • 65
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  • 4-bromo-1-oxo-1,2-dihydroisoquinoline-3-carbaldehyde [ No CAS ]
  • 66
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  • 5-Methyl-4-oxo-4,5-dihydro-thieno[3,2-c]quinoline-2-carboxylic acid [ No CAS ]
  • 67
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  • C10H8BrNO2 [ No CAS ]
  • 68
  • [ 69454-42-8 ]
  • N-(2-(4-benzylpiperidin-1-yl)ethyl)-5-methyl-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-2-carboxamide [ No CAS ]
  • 69
  • [ 69454-42-8 ]
  • methyl 5-methyl-4-oxo-4,5-dihydrothieno[3,2-c]quinoline-2-carboxylate [ No CAS ]
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  • [ 83-33-0 ]
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  • [ 945771-35-7 ]
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  • 1-(benzyloxy)-3-(chloromethyl)isoquinoline [ No CAS ]
  • 75
  • [ 69454-42-8 ]
  • 3-(azidomethyl)-1-(benzyloxy)isoquinoline [ No CAS ]
  • 76
  • [ 69454-42-8 ]
  • 3-(aminomethyl)isoquinolin-1(2H)-one [ No CAS ]
  • 77
  • C17H21NO6 [ No CAS ]
  • [ 69454-42-8 ]
YieldReaction ConditionsOperation in experiment
93% With hydrogenchloride; In 1,4-dioxane; dichloromethane; at 0 - 20℃; for 16h; To a stirred solution of methyl 2-((tert-butoxycarbonyl)amino)-2- (dimethoxyphosphoryl)acetate 2 (1.81 g, 6.1 mmol) in DCM (40 mL) at RT and under an inert atmosphere, were added DBU (927 mg, 6.1 mmol) and methyl 2-formylbenzoate 1 (1 g, 6.1 mmol). The mixture was stirred at RT for 16 h. The reaction mixture was diluted with water (30 mL) and extracted with DCM (2 chi 60 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified (silica gel; eluting with 20% EtOAc in hexanes) to afford the N-Boc derivative (1.6 g, 87%) as white solid. (0735) [00301] This derivative was dissolved in DCM (15 mL) and cooled to 0 C. To this was added 4 M HCI in 1,4-dioxane (5 mL). The reaction mixture was warmed to RT and stirred for 16 h. The mixture was concentrated under reduced pressure, and the obtained residue was diluted with water and extracted with DCM (2 chi 50 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2S04), filtered, and concentrated under reduced pressure to afford compound 3 (1 g, 93%) as white solid. 1H MR (400 MHz, CDC13): delta 9.07 (br s, 1H), 8.46 (d, J = 7.9 Hz, 1H), 7.60 - 7.78 (m, 3H), 7.38 (s, 1H), 3.99 (s, 3H); LCMS Mass: 203.9 (M++l).
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