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[ CAS No. 131885-33-1 ] {[proInfo.proName]}

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Chemical Structure| 131885-33-1
Chemical Structure| 131885-33-1
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Product Details of [ 131885-33-1 ]

CAS No. :131885-33-1 MDL No. :MFCD16744202
Formula : C9H11FN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 198.19 Pubchem ID :-
Synonyms :

Safety of [ 131885-33-1 ]

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Application In Synthesis of [ 131885-33-1 ]

* 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 [ 131885-33-1 ]

[ 131885-33-1 ] Synthesis Path-Downstream   1~30

  • 2
  • [ 131885-33-1 ]
  • [ 1026934-69-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In ethanol for 4h; Ambient temperature;
With hydrogen In methanol at 20℃; for 12h; 9.2 Step 2; 6-FLUORO-1-ISOPROPYL-13-DIHYDRO-2H-BENZIMIDAZOL-2-ONE; A mixture of (5-fluoro-2-nitrophenyl) ISOPROPYLAMINE (Step 1 of Example 9, 5. 85 g, 30 mmol) and 10% Pd-C (600 mg) in MEOH was stirred under atmosphere of hydrogen gas at at room temperature for 12 h. The catalyst was filtered off on a pad of Celite, and the filtrate was evaporated under reduced pressure. To the residue was added 1, I'-carbonyldiimidazole (4.5 g, 28 mmol) and THF (100 mL) and then stirred at 100°C for 10h. After cooling, the volatile materials were removed under reduced pressure and the residue was partitioned between ethylacetate and H2O. After extraction with ethylacetate (3 times), the combined organic phase was washed with brine, dried over MgS04 and concentrated. The residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (2: 1) to give 3.47 g (60%) of the title compound as a white solid. MS (ESI) m/z: 195 (M+H+), 193 (M-H+). I H NMR (CDC13) : 8 7.06-6. 99 (1 H, M), 6.90 (1 H, dd, J=9.2, 2.4 Hz), 6.82-6. 72 (1 H, M), 4.83-4. 62 (1 H, M), 1.54 (6 H, d, J=7.1 Hz)
With iron; ammonium chloride In ethanol; water at 85℃; for 3h; Inert atmosphere; 47a Step 47a: Preparation of 5-fluoro-N1-isopropylbenzene-1,2-diamine (Intermediate 501-91): 2,4-Difluoronitrobenzene (10 g, 62.9 mmol, 1.0 eq), isopropylamine (4.8 g, 81.8 mmol, 1.5 eq) and potassium carbonate (17.4 g, 125.8 mmol, 2.0 eq) were dissolved in DMF(150 mL) and reacted at room temperature for 18 hours. The LCMS check indicated reaction completion and the reaction was poured into water (400 mL) and stirred for 30 minutes to allow crystallize to precipitate out completely. The mixture was filtered and the filter cake was wash with water. _The filter cake was collected and dried in vacuum to give the product 5-fluoro-N-isopropyl-2-nitroaniline as a yellow solid (11.5 g, yield: 92.4%). The characterization data of this compound were: LCMS (ESI): m/z 199 [M + H]+. The compound obtained above (6.1 g, 62.9 mmol, 1.0 eq), iron powder (8.6 g, 154 mmol, 5.0 eq), ammonium chloride (8.2 g, 154 mmol, 3.0 eq) and water (20 mL) were dissolved in ethanol (100 mL). Under nitrogen protection condition, the reaction was heated to 85°C and reacted for 3 hours. The LCMS check indicated reaction completion. The reaction solution temperature was lowered to room temperature, and the reaction solution was poured into water (200 mL) and then dichloromethane was added (200 mL). The mixture was stirred for 5 minutes and filtered through celite and the filtrate was partitioned. The organic phase was dried over anhydrous sodium sulfate and the solvent was rotary evaporated to give the product 5-fluoro-N1-isopropylbenzene-1,2-diamine as a red oil (11.5 g, yield: 92.4%). The characterization data of this compound were: LCMS (ESI): m/z 169 [M + H]+.
  • 4
  • [ 75-15-0 ]
  • [ 399-52-0 ]
  • [ 131885-33-1 ]
  • 6-(5-fluoro-indol-1-yl)-1-isopropyl-1<i>H</i>-benzoimidazole-2-thiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-fluoro-1H-indole; (5-fluoro-2-nitrophenyl)isopropylamine With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 20h; Stage #2: With ammonium chloride; zinc In ethanol at 20 - 60℃; for 6h; Stage #3: carbon disulfide In ethanol at 90℃;
  • 6
  • [ 75-15-0 ]
  • [ 693-98-1 ]
  • [ 131885-33-1 ]
  • 1-isopropyl-6-(2-methyl-imidazol-1-yl)-1<i>H</i>-benzoimidazole-2-thiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-methylimidazole; (5-fluoro-2-nitrophenyl)isopropylamine With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 20h; Stage #2: With ammonium chloride; zinc In ethanol at 20 - 60℃; for 6h; Stage #3: carbon disulfide In ethanol at 90℃;
  • 7
  • [ 446-35-5 ]
  • [ 75-31-0 ]
  • [ 131885-33-1 ]
YieldReaction ConditionsOperation in experiment
92.4% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; 47a Step 47a: Preparation of 5-fluoro-N1-isopropylbenzene-1,2-diamine (Intermediate 501-91): 2,4-Difluoronitrobenzene (10 g, 62.9 mmol, 1.0 eq), isopropylamine (4.8 g, 81.8 mmol, 1.5 eq) and potassium carbonate (17.4 g, 125.8 mmol, 2.0 eq) were dissolved in DMF(150 mL) and reacted at room temperature for 18 hours. The LCMS check indicated reaction completion and the reaction was poured into water (400 mL) and stirred for 30 minutes to allow crystallize to precipitate out completely. The mixture was filtered and the filter cake was wash with water. _The filter cake was collected and dried in vacuum to give the product 5-fluoro-N-isopropyl-2-nitroaniline as a yellow solid (11.5 g, yield: 92.4%). The characterization data of this compound were: LCMS (ESI): m/z 199 [M + H]+. The compound obtained above (6.1 g, 62.9 mmol, 1.0 eq), iron powder (8.6 g, 154 mmol, 5.0 eq), ammonium chloride (8.2 g, 154 mmol, 3.0 eq) and water (20 mL) were dissolved in ethanol (100 mL). Under nitrogen protection condition, the reaction was heated to 85°C and reacted for 3 hours. The LCMS check indicated reaction completion. The reaction solution temperature was lowered to room temperature, and the reaction solution was poured into water (200 mL) and then dichloromethane was added (200 mL). The mixture was stirred for 5 minutes and filtered through celite and the filtrate was partitioned. The organic phase was dried over anhydrous sodium sulfate and the solvent was rotary evaporated to give the product 5-fluoro-N1-isopropylbenzene-1,2-diamine as a red oil (11.5 g, yield: 92.4%). The characterization data of this compound were: LCMS (ESI): m/z 169 [M + H]+.
88% With potassium carbonate In tetrahydrofuran at 0℃; for 13h; 9.1 EXAMPLE 9; 5-FLUORO-N-(T (4-HYDROXYTETRAHYDRO-2H-PYRAN-4-YL) METHYLLPIPERIDIN-4- YLLMETHYL)-3-ISOPROPYL-2-OXO-2, 3-DIKDRO-LH-BENZIMIDAZOLE-L-CARBOXAMIDE; Step 1; (5-FLUORO-2-NITROPHENYL . ISOPROPYLAMINE; To a stirred mixture OF 2, 4-DIFLUORO-1-NITROBENZENE (4.77 g, 30 mmol) and K2C03 (4.14 g, 30 mmol) in THF (30 mL) was added isopropyl amine (1.77g, 30 mmol) in THF (10 ML) at 0°C. After being stirred for 13h, the insoluble materials were removed by pad of Celite and the filtrate was consentrated under reduced pressure to give title compound (5.25 g, 88%) as a pale yellow oil. MS (ESI) m/z: 405 (M+H+). 1 H NMR (CDC13) : 8 8.21 (1 H, dd, J= 9.3, 6.0 Hz), 6. 48 (1 H, dd, J= 11.7, 2.6 Hz), 6.39-6. 29 (1 H, M), 3.81-3. 66 (1 H, M), 1. 33 (6 H, d, J=6.4 Hz)
77% In ethanol for 0.666667h; Heating;
In ethanol at 20℃; for 16h;

  • 8
  • [ 131885-33-1 ]
  • <i>N</i>2-isopropyl-4-pyrrol-1-yl-benzene-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: cesium carbonate / dimethylsulfoxide / 26 h / 100 - 140 °C 2: ammonium chloride; zinc / methanol / 2 h / 20 - 60 °C
  • 10
  • [ 131885-33-1 ]
  • 1-isopropyl-6-pyrrol-1-yl-1<i>H</i>-benzoimidazole-2-thiol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: cesium carbonate / dimethylsulfoxide / 26 h / 100 - 140 °C 2: ammonium chloride; zinc / methanol / 2 h / 20 - 60 °C 3: 60 mg / ethanol / 13 h / 88 - 95 °C
  • 11
  • [ 131885-33-1 ]
  • [ 709029-07-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: cesium carbonate / dimethylsulfoxide / 90 °C 2: zinc; ammonium chloride / ethanol / 20 °C 3: ethanol / 80 °C 4: cesium carbonate / dimethylformamide / 72 h / 60 °C
  • 12
  • [ 131885-33-1 ]
  • 6-imidazol-1-yl-1-isopropyl-1<i>H</i>-benzoimidazol-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: cesium carbonate / dimethylsulfoxide / 90 °C 2.1: zinc; ammonium chloride / methanol / 20 °C 2.2: morpholine / tetrahydrofuran
  • 13
  • [ 131885-33-1 ]
  • [ 131884-84-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: cesium carbonate / dimethylsulfoxide / 90 °C 2: zinc; ammonium chloride / ethanol / 20 °C 3: ethanol / 80 °C
  • 14
  • [ 131885-33-1 ]
  • 6-imidazol-1-yl-1-isopropyl-2-methanesulfinyl-1<i>H</i>-benzoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: cesium carbonate / dimethylsulfoxide / 90 °C 2: zinc; ammonium chloride / ethanol / 20 °C 3: ethanol / 80 °C 4: cesium carbonate / dimethylformamide / 72 h / 60 °C 5: meta-chloroperbenzoic acid / CHCl3; methanol / 0 - 20 °C
  • 15
  • [ 131885-33-1 ]
  • 6-imidazol-1-yl-1-isopropyl-2-methanesulfonyl-1<i>H</i>-benzoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: cesium carbonate / dimethylsulfoxide / 90 °C 2: zinc; ammonium chloride / ethanol / 20 °C 3: ethanol / 80 °C 4: cesium carbonate / dimethylformamide / 72 h / 60 °C 5: meta-chloroperbenzoic acid / CHCl3; methanol / 20 °C
  • 16
  • [ 131885-33-1 ]
  • [ 151448-19-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: H2 / 5percent Pd/C / ethanol / 4 h / Ambient temperature 2: EtNiPr2 / toluene / 1.) from -78 deg C to RT, 16 h, 2.) reflux, 24 h
  • 17
  • [ 131885-33-1 ]
  • 7-Fluoro-5-isopropyl-3-phenyl-5H-imidazo[1,5-a]quinoxalin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: H2 / 5percent Pd/C / ethanol / 4 h / Ambient temperature 2: EtNiPr2 / toluene / 1.) from -78 deg C to RT, 16 h, 2.) reflux, 24 h 3: 1.) KOtBu / 1.) THF, from -20 deg C to 0 deg C, 45 min, 2.) THF, from -40 deg C to RT, 30 min 4: KOtBu / tetrahydrofuran / 3 h / -78 - 20 °C
  • 18
  • [ 131885-33-1 ]
  • 7-Fluoro-3-(4-fluoro-phenyl)-5-isopropyl-5H-imidazo[1,5-a]quinoxalin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: H2 / 5percent Pd/C / ethanol / 4 h / Ambient temperature 2: EtNiPr2 / toluene / 1.) from -78 deg C to RT, 16 h, 2.) reflux, 24 h 3: 1.) KOtBu / 1.) THF, from -20 deg C to 0 deg C, 45 min, 2.) THF, from -40 deg C to RT, 30 min 4: KOtBu / tetrahydrofuran / 3 h / -78 - 20 °C
  • 19
  • [ 131885-33-1 ]
  • 7-Fluoro-5-isopropyl-3-(4-methoxy-phenyl)-5H-imidazo[1,5-a]quinoxalin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: H2 / 5percent Pd/C / ethanol / 4 h / Ambient temperature 2: EtNiPr2 / toluene / 1.) from -78 deg C to RT, 16 h, 2.) reflux, 24 h 3: 1.) KOtBu / 1.) THF, from -20 deg C to 0 deg C, 45 min, 2.) THF, from -40 deg C to RT, 30 min 4: KOtBu / tetrahydrofuran / 3 h / -78 - 20 °C
  • 20
  • [ 131885-33-1 ]
  • [ 1027167-17-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: H2 / 5percent Pd/C / ethanol / 4 h / Ambient temperature 2: EtNiPr2 / toluene / 1.) from -78 deg C to RT, 16 h, 2.) reflux, 24 h 3: 1.) KOtBu / 1.) THF, from -20 deg C to 0 deg C, 45 min, 2.) THF, from -40 deg C to RT, 30 min
  • 21
  • [ 131885-33-1 ]
  • 1-(2-((5-amino-4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxyphenyl)amino)pyrimidin-4-yl)-5-fluoro-3-isopropyl-1H-benzo[d]imidazol-2(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: ammonium chloride; iron / water; ethanol / 3 h / 85 °C / Inert atmosphere 2: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 3: caesium carbonate / N,N-dimethyl-formamide / 20 °C 4: hydrogenchloride / water; isopropyl alcohol / 18 h / 85 °C 5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / Reflux 6: ammonium chloride; iron / water; ethanol / 3 h / 85 °C
  • 22
  • [ 131885-33-1 ]
  • 6-fluoro-1-isopropyl-1,3-dihydro-2H-benzo[d]imidazol-2(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonium chloride; iron / water; ethanol / 3 h / 85 °C / Inert atmosphere 2: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere
  • 23
  • [ 131885-33-1 ]
  • 1-(2-chloropyrimidin-4-yl)-5-fluoro-3-isopropyl-1H-benzo[d]imidazol-2(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ammonium chloride; iron / water; ethanol / 3 h / 85 °C / Inert atmosphere 2: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 3: caesium carbonate / N,N-dimethyl-formamide / 20 °C
  • 24
  • [ 131885-33-1 ]
  • 1-(2-((4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxy-5-nitrophenyl)amino)pyrimidin-4-yl)-5-fluoro-3-isopropyl-1H-benzo[d]imidazol-2(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: ammonium chloride; iron / water; ethanol / 3 h / 85 °C / Inert atmosphere 2: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 3: caesium carbonate / N,N-dimethyl-formamide / 20 °C 4: hydrogenchloride / water; isopropyl alcohol / 18 h / 85 °C 5: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / Reflux
  • 25
  • [ 131885-33-1 ]
  • N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-5-(4-(5-fluoro-3-isopropyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)pyrimidin-2-ylamino)-4-methoxyphenyl)acrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: ammonium chloride; iron / water; ethanol / 3 h / 85 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 3.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C 4.1: hydrogenchloride / water; isopropyl alcohol / 18 h / 85 °C 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 18 h / Reflux 6.1: ammonium chloride; iron / water; ethanol / 3 h / 85 °C 7.1: tetrahydrofuran / 0.5 h / 0 °C 7.2: 18 h / Reflux
  • 26
  • [ 131885-33-1 ]
  • 1-(2-((4-fluoro-2-methoxy-5-nitrophenyl)amino)pyrimidin-4-yl)-5-fluoro-3-isopropyl-1H-benzo[d]imidazol-2(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: ammonium chloride; iron / water; ethanol / 3 h / 85 °C / Inert atmosphere 2: triethylamine / dichloromethane / 0.5 h / 0 - 5 °C / Inert atmosphere 3: caesium carbonate / N,N-dimethyl-formamide / 20 °C 4: hydrogenchloride / water; isopropyl alcohol / 18 h / 85 °C
  • 27
  • [ 131885-33-1 ]
  • C9H10FIN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-iodo-succinimide; acetic acid at 60℃; for 2h;
  • 28
  • [ 131885-33-1 ]
  • C9H12FIN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; N-iodo-succinimide / 2 h / 60 °C 2: iron; ammonium chloride / ethanol; water / 16 h / 20 °C
  • 29
  • [ 131885-33-1 ]
  • C10H10FIN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid; N-iodo-succinimide / 2 h / 60 °C 2: iron; ammonium chloride / ethanol; water / 16 h / 20 °C 3: methanol / 1 h / 70 °C
  • 30
  • [ 131885-33-1 ]
  • 1-((3S,5R)-1-acryloyl-5-(methoxymethyl)pyrrolidin-3-yl)-3-((6-fluoro-1-isopropyl-1H-benzo[d]imidazol-5-yl)ethynyl)-5-(methylamino)-1H-pyrazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: acetic acid; N-iodo-succinimide / 2 h / 60 °C 2: iron; ammonium chloride / ethanol; water / 16 h / 20 °C 3: methanol / 1 h / 70 °C 4: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 2 h / 90 °C
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