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[ CAS No. 887399-27-1 ]

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Chemical Structure| 887399-27-1
Chemical Structure| 887399-27-1
Structure of 887399-27-1 * Storage: {[proInfo.prStorage]}

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Product Details of [ 887399-27-1 ]

CAS No. :887399-27-1 MDL No. :MFCD26407106
Formula : C14H13N3O Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :239.27 g/mol Pubchem ID :59397049
Synonyms :

Safety of [ 887399-27-1 ]

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 [ 887399-27-1 ]

  • Downstream synthetic route of [ 887399-27-1 ]

[ 887399-27-1 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 641571-13-3 ]
  • [ 887399-27-1 ]
  • [ 887399-28-2 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; [00106] To a solution of 6-(3-Amino-phenylamino)-l ,3-dihydro-indol-2-one (36 mg, 0.15 mmol) and 3-(4-methyl-imidazol-l-yl)-5-trifluoromethyl-benzoic acid (53 mg, 0.195 mmol) in DMF (1.5 mL) is added N,N-diisopropylethylamine (78 muL, 0.45 mmol) followed by addition of HATU (63 mg, 0.165 mmol). The mixture is stirred at ambient temperature overnight. The mixture is diluted with EtOAc and washed with 10% Na2S2O3 aqueous solution and brine. The organic layer is separated, dried over MgSO4, EPO <DP n="36"/>and concentrated. The crude product is used in the next step without further purification: LC-MS: 492.1 (MH+).
  • 2
  • [ 887399-26-0 ]
  • [ 887399-27-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogen; acetic acid 1 [00105] To a solution of 2-nitro-4-(3-nitro-phenylamino)-phenyl]-acetic acid(317mg, 1 mmol) in acetic acid (5 mL) is added 10% Pd/C (48 mg). The mixture is put on a Parr shaker (60 psi) overnight. The catalyst is filtered and the solvent is evaporated to dryness. The crude product is purified by column chromatography (EtOAc/Hexane=9: 1) to give the desired product: 1H NMR (400 MHz, CD3OD) δ .6.90 (s, 1 H), 6.92 (t, 1 H), 6.65-6.60 (m, 2 H), 6.45 (s, 1 H), 6.4 (d, 1 H); 6.23 (d, IH), 3.37 (s, 2H); LC-MS: 240.4 (MH+).
  • 3
  • [ 887399-27-1 ]
  • [ 887399-47-5 ]
  • [ 887399-46-4 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20.0℃; To a solution of 6-(3-amino-phenylamino)-1,3-dihydro-indol-2-one (120 mg, 0.50 mmol, prepared as described in Example 1) and 4-(4-ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-benzoic acid hydrochloride (213 mg, 0.60mmol) in DMF (5 mL) is added N,N-diisopropylethylamine (437 muL, 2.5 mmol) followed by addition of HATU (191 mg, 0.50 mmol). The mixture is stirred at ambient temperature overnight. The mixture is dilute with EtOAc and washed with 10% Na2S2O3 aqueous solution and brine. The organic layer is separated, dried over MgSO4, and concentrated. The crude is purified by column chromatography (CH2Cl2/CH3OH=9:1) to give the desired compound. LC-MS: 538.2 (MH+).
  • 4
  • [ 887399-27-1 ]
  • [ 329-01-1 ]
  • [ 1033771-64-0 ]
YieldReaction ConditionsOperation in experiment
94% With triethylamine In tetrahydrofuran at 20℃; for 3h; 1 Synthesis of l-[3-(2-oxo-2,3-dihydro-lH-indol-6-ylamino)phenyl]-3-(3- trifluoro-methylphenyl)urea (6); [00100] To a solution of 6-(3-aminophenylamino)-l,3-dihydroindol-2-one (800 mg, 3.34 mmol) in THF (35 mL) are added 3-(trifluoromethyl)phenyl isocyanate (506 μL, 3.67 mmol) and triethyl amine (1.4 mL, 10 mmol). The mixture is stirred at room temperature for 3 hr. It is then concentrated and purified by column chramatography (EtOAc/hexane, gradient, 0-100%) to give the desired product. LC-MS (m/z) 427.1 (MM).
With triethylamine In tetrahydrofuran at 20℃;
  • 5
  • [ 887399-27-1 ]
  • [ 32315-10-9 ]
  • [ 163733-96-8 ]
  • [ 1033771-66-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: bis(trichloromethyl) carbonate; 3,4,5-trifluoro aniline With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.25h; Stage #2: 6-(3-aminophenylamino)indolin-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.533333h; 2 Example 2; l-|3-r2-oxo-3-(lH-pyrrol-2-ylmethylene)-2,3-dihvdro-lH-indol-6-ylaminol-phenyl)-3-(3A5-trifluorophenyl)urea; [00103] Synthesis of l-[3-(2-oxo-2,3-dihydro-lH-indol-6-ylamino)phenyl]-3-(3,4,5-trifluoro-phenyl)urea (8); [00104] A solution of 3,4,5-trifluoroaniline (14.7 mg, 0.1 mmol) and diisopropylethylamine (38 μL, 0.22 mmol) in CH2Cl2 (2 mL) is added drop wise to a solution of triphosgene (11 mg, 0.37 mmol) in CH2Cl2 (1 mL) under N2. The mixture is stirred at room temperature for 15 min. This solution is added drop wise to a solution of 6-(3-aminophenylamino)-l,3-dihydroindol-2-one (5, 20 mg, 0.084 mmol) and diisopropylethylamine (32 μL, 0.18 mmol) in CH2Cl2 (2 mL) over 2 min. The mixture is stirred at room temperature for 30 min. After solvent removal in vacuo, the crude product is used in the next step without further purification. LC-MS (m/z) 413.1 [M++l].
  • 6
  • [ 887399-27-1 ]
  • [ 1033771-68-4 ]
  • [ 1033771-70-8 ]
YieldReaction ConditionsOperation in experiment
In toluene at 85℃; 3 Synthesis of l-[3-(2-oxo-2,3-dihydro-lH-indol-6-ylamino)phenyl]-3-(2,4,5-trifluoro-phenyl)urea (11); [00110] To a suspension of 6-(3-aminophenylamino)-l,3-dihydroindol-2-one (5,310 mg, 1.30 mmol) in toluene (15 mL) is added 2,4,5-trifluorobenzoyl azide (392 mg, 1.95 mmol)). The mixture is heated at 80 0C overnight. After cooling to room temperature, the mixture is concentrated and the crude is purified by column chromatography (silica gel, EtOAc/hexane, gradient, 0-100%) to give the desired product. LC-MS (m/z) 413.1 (M++l).
  • 7
  • [ 1033771-61-7 ]
  • [ 887399-27-1 ]
YieldReaction ConditionsOperation in experiment
51% With hydrogen; acetic acid at 20℃; 1 Synthesis of 6-(3-aminophenylamino)-l,3-dihydroindol-2-one (5); [0098] To a solution of [2-nitro-4-(3-nitrophenylamino)phenyl]acetic acid ethyl ester (14.6 g, 0.042 mol) in acetic acid (250 mL) is added 10% Pd/C (10 wt%, 1.46 g).The mixture is stirred under a hydrogen balloon at room temperature overnight. The mixture is filtered through Celite. The filtrate is concentrated and purified (silica gel,EtOAc/hexane, gradient, 0-100%) to give the desired product. 1H NMR (400 MHz,DMSO-(I6) δ 10.18 (s, 1 H), 7.76 (s, 1 H), 6.98 (d, 1 H), 6.85 (t, 1 H), 6.58 (d, 1 H), 6.55(m, 1 H), 6.35 (m, 1 H), 6.25-6.20 (m, 1 H), 6.10-6.05 (m, 1 H), 4.91 (s, 2 H), 3.33 (s, 2H); LC-MS (m/z) 240.1 (M++l).
51% With palladium 10% on activated carbon; hydrogen In acetic acid at 20℃;
  • 10
  • [ 199328-35-3 ]
  • [ 887399-27-1 ]
  • 12
  • 4-(4-methylpiperazin-1-yl)-3-(trifluoromethyl)benzoic acid [ No CAS ]
  • [ 887399-27-1 ]
  • C27H26F3N5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃;
  • 17
  • [ 6127-11-3 ]
  • [ 887399-27-1 ]
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