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[ CAS No. 1190380-38-1 ] {[proInfo.proName]}

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Chemical Structure| 1190380-38-1
Chemical Structure| 1190380-38-1
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Product Details of [ 1190380-38-1 ]

CAS No. :1190380-38-1 MDL No. :MFCD17214360
Formula : C9H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :VNYNRNAJJGDULT-UHFFFAOYSA-N
M.W :162.19 Pubchem ID :52911247
Synonyms :

Safety of [ 1190380-38-1 ]

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 [ 1190380-38-1 ]

* 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 [ 1190380-38-1 ]

[ 1190380-38-1 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 1190380-36-9 ]
  • [ 1190380-38-1 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 2-methyl-5-nitroisoindolin-1-one With hydrogenchloride; iron(0) In ethanol at 95℃; for 3h; Inert atmosphere; Stage #2: With ammonia In methanol; ethanol 62 A mixture of Intermediate 60 (68 mg), Fe (180 mg), and HCl (53 μl), in EtOH (3 ml), was refluxed at 950C under N2 for 3 h. The reaction was basified with a few drops of 2M NH3 in MeOH then concentrated under vacuum. The residues were taken up in 20% MeOH in DCM, filtered twice through a plug of silica gel, and the filtrate was concentrated under vacuum to give the desired product (58 mg, 99%). 1H NMR (400 MHz, DMSO-^6) δ ppm 2.96 (s, 3 H), 4.24 (s, 2 H), 5.75 (br. s, 2 H), 6.54 - 6.64 (m, 2 H), 7.27 (d, /=7.78 Hz, 1 H); m/z (ES+APCI)+ : 163 [M+H]+.
96.94% With palladium on activated charcoal; hydrogen In methanol for 8h; EN-5 (1.1g, 5.72mmol, 1 equiv) was dissolved in methanol stirred at room temperature, and then Pd/C (150mg, 0.014mmol, 0.05 equiv) was added to the solution. The reaction mixture was stirred at room temperature for 8h under the protection of hydrogen and TLC analysis indicated the reaction was completed. After completed, filter off Pd/C with celite to get filtrate, concentrated to give the desired product (29b). It was obtained as a gray solid 0.9g in 96.94% yield. 1H NMR (400MHz, DMSO-d6) δ 7.28 (d, J=8.1Hz, 1H), 6.62 - 6.56 (m, 2H), 5.72 (s, 2H), 4.24 (s, 2H), 2.97 (s, 3H).
85% With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 7h;
81% With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 2h; 52.3 5-amino-2-methylisoindolin-1-one The compound 2-methyl-5-nitroisoindolin-1-one 52c (920 mg, 4.8 mmol) was dissolved in ethyl acetate (50 mL),Then, 10% palladium-carbon (400 mg) was added, and the mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours.After the reaction was completed, the filtrate was filtered, and the solvent was removed under reduced pressure.The target product 5-amino-2-methylisoindolin-1-one 52d (630 mg, off-white solid) was obtained in a yield of 81%.
81% With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 2h; 52.3 5-Amino-2-methylisoindol-1-one Compound 2-methyl-5-nitroisoindolin-1-one 52c (920 mg, 4.8 mmol) was dissolved in ethyl acetate (50 mL), then 10% palladium on carbon (400 mg) was added, and under hydrogen atmosphere Stir at room temperature for 2 hours.After the completion of the reaction, it was filtered, and the filtrate was removed from the solvent under reduced pressure to obtain the target product 5-amino-2-methylisoindol-1-one 52d (630 mg, nearly white solid), yield: 81%.
81% With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 2h; 52.3 5-Amino-2-methylisoindol-1-one Compound 2-methyl-5-nitroisoindolin-1-one 52c (920 mg, 4.8 mmol) was dissolved in ethyl acetate (50 mL), then 10% palladium on carbon (400 mg) was added, and under hydrogen atmosphere Stir at room temperature for 2 hours.After the completion of the reaction, it was filtered, and the filtrate was removed from the solvent under reduced pressure to obtain the target product 5-amino-2-methylisoindol-1-one 52d (630 mg, nearly white solid), yield: 81%.
30% With iron(0); ammonia hydrochloride In ethanol; lithium hydroxide monohydrate at 90℃; for 1h; 61 5-Amino-2-meth lisoindolin-1-one (61.5) Fe (350 mg, 6.2 mmol) and NH4Cl (337 mg, 6.2 mmol) were added to the solution of 2-methyl-5-nitroisoindolin-1-one (61.4) (200 mg, 1.0 mmol) in EtOH (10 mL) and H2O (1 mL). The mixture was stirred at 90 °C for 1 h. After cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated to afford the crude product. The crude product was purified by column chromatography (ethyl acetate/hexane: 1/10) to afford 5-amino-2-methylisoindolin-1-one (61.5) as a brown solid (50 mg, 30%). [00875] LCMS: 163.1 [M+1]+.
With stannous chloride In ethanol at 79℃; for 2h; 45a.2 Step 2: 5-ammo-2-methylisoindolm-1-one The 2-methyl-5-nitroisoindolin-1-one (50 mg, 0.26 ϖunol) was dissolved in EtOH (1.3 ml) with heating, and tin chloride (117 mg, 0.52 mmol) added. The solution was stirred at 79 °C for 2 hours. The mixture was cooled to RT, diluted with 4:1 water: saturated sodium bicarbonate (aq, 100 ml), extracted with EtOAc (3x100 ml), the organics combined, washed with brine, dried over Na2SO4, filtered and the volatiles removed in vacuum. The product was purified by chromatography on SiO2 eluting with 5% MeOH : DCM +1% TEA to give the titled compound. LRMS calc: 162.08; obs: 163.18 (M+l).

  • 2
  • [ 1975-51-5 ]
  • [ 1190380-38-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sulfuric acid / water / 20 - 55 °C 2.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 79 °C / Inert atmosphere 2.2: 2 h / 20 °C 3.1: tin(ll) chloride / ethanol / 2 h / 79 °C
Multi-step reaction with 4 steps 1: thionyl chloride / 2 h / 0 - 80 °C 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 80 °C 3: methanol / 2 h / 20 °C 4: iron; ammonium chloride / water; ethanol / 1 h / 90 °C
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C 2: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 21 h / 85 °C 3: triethylamine / methanol / 24 h / Inert atmosphere; Reflux 4: hydrogenchloride; iron / ethanol / 3 h / 95 °C / Inert atmosphere
  • 4
  • [ 1190380-38-1 ]
  • (R)-1-(3-((2-chloro-5-fluoropyrimidin-4-yl)amino)piperidin-1-yl)prop-2-en-1-one [ No CAS ]
  • (R)-5-(4-(1-acryloylpiperidin-3-ylamino)-5-fluoropyrimidin-2-ylamino)-2-methylisoindolin-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; DavePhos In tert-Amyl alcohol at 100℃; for 1h; Inert atmosphere; 61 (R)-5-(4-(1-Acryloylpiperidin-3-ylamino)-5-fluoropyrimidin-2-ylamino)-2- methylisoindolin-1-one (I-61) (R)-1-(3-(2-Chloro-5-fluoropyrimidin-4-ylamino)piperidin-1-yl)prop-2-en-1-one (intermediate B, 130 mg, 0.46 mmol) and Cs2CO3 (295 mg, 0.91 mmol) were added to the solution of 5-amino-2-methylisoindolin-1-one (61.5) (44 mg, 0.27 mmol) in tert-amyl alcohol (4 mL). Tris(dibenzylideneacetone)dipalladium(0) (41 mg, 0.046 mmol) and DavePhos (18 mg, 0.046mmol) were added under N2. The reaction mixture was stirred at 100 °C for 1 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated to afford the crude product. The crude product was purified by column chromatography (DCM/MeOH: 10/1) to afford (R)-5-(4-(1-acryloylpiperidin-3-ylamino)-5-fluoropyrimidin-2-ylamino)-2- methylisoindolin-1-one (I-61) as a yellow solid (50 mg, 45%). [00878] Mp: 120-122 °C [00879] LCMS: 411.3 [M+1]+. [00880] 1H NMR (400 MHz, DMSO-d6): δ 1.42-1.48 (m, 1H), 1.65-1.70 (m, 1H), 1.81-1.85 (m, 1H), 1.99-2.01 (m, 1H), 2.65-2.84 (m, 1H), 2.99-3.05 (m, 3.5H), 3.12-3.18 (m, 0.5H), 4.02- 4.05 (m, 2H), 4.18-4.38 (m, 2.5H), 4.50-4.54 (m, 0.5H), 5.45 (d, 0.5H), 5.72-5.75 (m, 0.5H), 6.00 (d, 0.5H), 6.15 (dd, 1H), 6.60-6.66 (m, 0.5H), 6.86-6.93 (m, 0.5H), 7.45-7.64 (m, 3H), 7.96- 8.10 (m, 2H), 9.51 (d, J = 8 Hz, 1H).
  • 6
  • [ 1190380-38-1 ]
  • [ 16727-47-2 ]
  • 5-(2,6-bis-benzyloxy-pyridin-3-ylamino)-2-methyl-2,3-dihydro-isoindol-1-one [ No CAS ]
  • 7
  • [ 372118-01-9 ]
  • [ 1190380-38-1 ]
  • methyl 6-chloro-4-((2-methyl-1-oxoisoindolin-5-yl)amino)pyridazine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% In ethanol; at 90℃; for 3h;Microwave irradiation; Compound <strong>[372118-01-9]4,6-dichloropyridazine-3-carboxylic acid methyl ester</strong> 1a (310 mg, 1.50 mmol)And 5-amino-2-methylisoindolin-1-one 52d (267 mg, 1.65 mmol) were dissolved in ethanol (20 mL), and then heated to 90 C. in a microwave reactor and stirred for 3 hours.After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane / methanol = 100/1 to 20/1),The target product 6-chloro-4-((2-methyl-1-oxoisoindolin-5-yl) amino) pyridazine-3-carboxylic acid methyl ester 52e (120 mg, pale yellow solid) was obtained,Yield: 24%.
  • 8
  • [ 1190380-38-1 ]
  • methyl 6-(2,6-difluorophenyl)-4-((2-methyl-1-oxoisoindol-5-yl)amino)pyridazine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 3 h / 90 °C / Microwave irradiation 2: N-ethyl-N,N-diisopropylamine; tetrakis-(triphenylphosphine)-palladium / 1,4-dioxane / 1 h / 110 °C / Microwave irradiation; Inert atmosphere
Multi-step reaction with 2 steps 1: ethanol / 3 h / 90 °C / Microwave irradiation 2: tetrakis-(triphenylphosphine)-palladium; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 110 °C / Inert atmosphere; Microwave irradiation
  • 9
  • [ 1190380-38-1 ]
  • 6-(2,6-difluorophenyl)-4-((2-methyl-1-oxo-2,3-dihydro-1H-isoindol-5-yl)amino)pyridazine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 3 h / 90 °C / Microwave irradiation 2: N-ethyl-N,N-diisopropylamine; tetrakis-(triphenylphosphine)-palladium / 1,4-dioxane / 1 h / 110 °C / Microwave irradiation; Inert atmosphere 3: ammonium hydroxide / tetrahydrofuran / 15 h / 20 °C
Multi-step reaction with 3 steps 1: ethanol / 3 h / 90 °C / Microwave irradiation 2: tetrakis-(triphenylphosphine)-palladium; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 1 h / 110 °C / Inert atmosphere; Microwave irradiation 3: ammonia / tetrahydrofuran / 15 h / 20 °C
  • 10
  • [ 7677-24-9 ]
  • [ 1190380-38-1 ]
  • [ 67-64-1 ]
  • C13H15N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With zinc(II) chloride at 40℃; for 2h; 4.1.21 Synthesis of 2-methyl-2-((1-oxo-1,3-dihydroisobenzofuran-5-yl)amino)propanenitrile (30a) General procedure: 29a (0.5g, 3.35mmol, 1 equiv) was reacted with TMSCN (1.26mL, 10.06mmol, 3 eqviu) using ZnCl2 (46mg, 0.33mmol, 0.1 equiv) in 2mL Acetone at the temperature of 40 for 2h. After work up, the solution was concentrated. Then the solution was extracted with EtOAc, the organic phase was washed with saturated brine, dried over Na2SO4, filtered, concentrated and purified by silica gel chromatography (30%-60% EtOAc/hexanes) to give the desired product. It was obtained as a white solid 576mg in 78.22% yield. 1H NMR (400MHz, DMSO-d6) δ 7.63 (d, J=9.0Hz, 0H), 7.18 (s, 0H), 6.97 (d, J=2.1Hz, 0H), 6.96 - 6.94 (m, 0H), 5.29 (s, 0H), 1.72 (s, 1H).
  • 11
  • [ 1190380-38-1 ]
  • 4-(4,4-dimethyl-3-(2-methyl-1-oxoisoindolin-5-yl)-5-oxo-2-thioxoimidazolidin-1-yl)-2-(trifluoromethyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: zinc(II) chloride / 2 h / 40 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C 2.2: 1 h / 20 - 25 °C 2.3: 2 h / 80 °C
YieldReaction ConditionsOperation in experiment
61% Stage #1: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 20h; Inert atmosphere; Stage #2: In methanol at 20℃; for 2h; 9.1 Synthesis method: General procedure: Dissolve methyl 2-methyl-4-nitrobenzoate (0.50g, 2.56mmol) in CCl4 (10ml), add NBS (0.68g, 3.84mmol), AIBN (42mg, 0.25mmol), Reaction under nitrogen, heating at 80°C and refluxing for 20 hours. After the reaction was monitored by TLC, the reaction was cooled to room temperature and filtered with suction. The filtrate was concentrated, and the concentrate was added to the methanol solution of N,N-dimethylethylenediamine (2M, 5ml). As long as it was easy to handle at room temperature for 2h, the reaction solution was concentrated and passed Purification by silica gel column chromatography (DCM/MeOH=10/1) gave the target product 284 mg with a yield of 44%.
  • 13
  • [ 1190380-38-1 ]
  • 2-(4-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)-2,5-dioxopiperazin-1-yl)-3-phenylpropionic acid [ No CAS ]
  • 2-(4-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)-2,5-dioxopiperazin-1-yl)-N-(2-methyl-1-oxoisoindolin-5-yl)-3-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With 1-propanephosphonic acid cyclic anhydride; N-ethyl-N,N-diisopropylamine In ethyl acetate at 70℃; for 4h; 12 Example 12 2-(4-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)-2,5-dioxapiperazin-1-yl)-N-(2-methyl-1-oxoisoindolin-5-yl)-3-phenylpropanamide 2-(4-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)-2,5-dioxapiperazin-1-yl)-3-phenylpropionic acid 1i( 50 mg, 113.42 μmol) and 5-amino-2-methylisoindol-1-one 12a (27.59 mg, 170.13 μmol) were dissolved in ethyl acetate (5 mL),N,N-diisopropylethylamine (87.95 mg, 680.52 μmol) and 1-propylphosphoric anhydride (216.53 mg, 340.26 μmol, 50% ethyl acetate solution) were added, and the mixture was reacted at 70° C. for 4 hours.After the reaction was completed, it was concentrated under reduced pressure, and the obtained residue was further separated and purified by silica gel column chromatography (eluent: B system),yields 2-(4-(5-Chloro-2-(1H-tetrazol-1-yl)phenyl)-2,5-dioxapiperazin-1-yl)-N-(2-methyl- 1-oxoisoindolin-5-yl)-3-phenylpropanamide 12 (35 mg), yield: 52%.
  • 14
  • [ 1190380-38-1 ]
  • [ 868066-91-5 ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: 5-amino-2-methylisoindolin-1-one With hydrogen bromide; NaNO2 In lithium hydroxide monohydrate; acetonitrile at 0℃; for 0.5h; Inert atmosphere; Stage #2: With copper(II) bromide In lithium hydroxide monohydrate; acetonitrile at 0 - 20℃; for 2h; Inert atmosphere;
  • 15
  • [ 1190380-38-1 ]
  • [ 926308-01-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: NaNO2; hydrogen bromide / acetonitrile; lithium hydroxide monohydrate / 0.5 h / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: 1-methyl-pyrrolidin-2-one / 1 h / 220 °C / Microwave irradiation; Inert atmosphere 3.1: boron trifluoride diethyl ether complex; sulfuric acid / 168 h / Reflux; Inert atmosphere
  • 16
  • [ 1190380-38-1 ]
  • 2-methyl-1-oxoisoindoline-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaNO2; hydrogen bromide / acetonitrile; lithium hydroxide monohydrate / 0.5 h / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: 1-methyl-pyrrolidin-2-one / 1 h / 220 °C / Microwave irradiation; Inert atmosphere
  • 17
  • [ 1190380-38-1 ]
  • methyl 3-(6-bromo-2-methyl-3-oxoisoindolin-1-yl)-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaNO2; hydrogen bromide / acetonitrile; lithium hydroxide monohydrate / 0.5 h / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: tetra-n-butylammonium azide; tetra-n-butylammonium tetrafluoroborate / acetonitrile / 0.33 h / 20 °C / Electrochemical reaction; Inert atmosphere
  • 18
  • [ 1190380-38-1 ]
  • methyl 3-(3-methoxy-3-oxo-1-phenylpropyl)-2-methyl-1-oxoisoindoline-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: NaNO2; hydrogen bromide / acetonitrile; lithium hydroxide monohydrate / 0.5 h / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: 1-methyl-pyrrolidin-2-one / 1 h / 220 °C / Microwave irradiation; Inert atmosphere 3.1: boron trifluoride diethyl ether complex; sulfuric acid / 168 h / Reflux; Inert atmosphere 4.1: tetra-n-butylammonium azide; tetra-n-butylammonium tetrafluoroborate / acetonitrile / 1 h / 20 °C / Electrochemical reaction; Inert atmosphere
  • 19
  • [ 1190380-38-1 ]
  • methyl 3-(6-cyano-2-methyl-3-oxoisoindolin-1-yl)-3-phenylpropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: NaNO2; hydrogen bromide / acetonitrile; lithium hydroxide monohydrate / 0.5 h / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: 1-methyl-pyrrolidin-2-one / 1 h / 220 °C / Microwave irradiation; Inert atmosphere 3.1: tetra-n-butylammonium azide; tetra-n-butylammonium tetrafluoroborate / acetonitrile / 1 h / 20 °C / Electrochemical reaction; Inert atmosphere
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