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Chemical Structure| 380605-28-7

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Product Details of [ 380605-28-7 ]

CAS No. :380605-28-7
Formula : C8H9N3O2
M.W : 179.18
SMILES Code : O=[N+](C1=C(NC2CC2)C=CN=C1)[O-]
MDL No. :MFCD11184481
InChI Key :OXWIUZUWZJVMSR-UHFFFAOYSA-N
Pubchem ID :22349359

Safety of [ 380605-28-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 380605-28-7 ]

* 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 [ 380605-28-7 ]

[ 380605-28-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 380605-28-7 ]
  • [ 146950-68-7 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 2585.81 Torr; Step 2: Synthesis of N'-cyclopropylpyridine-S^-diamine 5-c5- b (167 g, 932 mmol) in ethanol (1400 mL) was hydrogenated (50 Psi) at 20C with wet 10%) Pd/C (34 g) as a catalyst overnight. After uptake of H2 (3 eq.), the catalyst was filtered off and the filtrate was evaporated. The residue was washed with MTBE to afford compound 5-c as a yellow powder (133 g, 95%).
95% With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 2585.81 Torr; Intermediate 7-b (167 g, 932 mmol) in ethanol (1400 mL) was hydrogenated (50 Psi) at 20C with wet 10 % Pd/C (34 g) as a catalyst overnight. After uptake of H2 (3 eq), the catalyst was filtered off and the filtrate was evaporated. The residue was washed with methyl terbutyl ether to afford the title compound 7-c (133 g, 95%) as a yellow powder.
95% With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 2585.81 Torr; Step 2: Synthesis of N4-cyclopropylpyridine-3,4-diamine(5-c)A mixture of the intermediate 5-b (167 g, 932 mmol) in ethanol (1400 mL) was hydrogenated (50 Psi) at 20C with wet 10% Pd/C (34 g) as a catalyst overnight. After uptake of H2 (3 eq.), the catalyst was filtered off and the filtrate was evaporated. The residue was washed with MTBE to afford compound 5-c as a yellow powder (133 g, 95%).
95% With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; under 2585.81 Torr; Intermediate 10-b (167 g, 932 mmol) in ethanol (1400 mL) was hydrogenated (50 Psi) at 20C with wet 10 % Pd/C (34 g) as a catalyst overnight. After uptake of H2 (3 eq), the catalyst was filtered off and the filtrate was evaporated. The residue was washed with methyl tert-butyl ether to afford the title compound 10-c as a yellow powder (133 g, 95%).
95% With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; under 2585.81 Torr; Intermediate 7-b (167 g, 932 mmol) in ethanol (1400 mL) was hydrogenated (50 Psi) at 20 C. with wet 10% Pd/C (34 g) as a catalyst overnight. After uptake of H2 (3 eq), the catalyst was filtered off and the filtrate was evaporated. The residue was washed with methyl terbutyl ether to afford the title compound 7-c (133 g, 95%) as a yellow powder.
90.6% With hydrogen;palladium 10% on activated carbon; In ethanol; water; at 20℃; under 2585.81 Torr; for 16.0h; The synthesis of l-(cyclopropyl)-l,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one (fragment CI) was done as shown in scheme 7.g 7 fragment C1; Scheme 7A round-bottom flask was charged with 3-nitro-4-chloropyridine (600 g, 3.8 mol), absolute EtOH (3L), diisopropylethylamine (DIPEA) (1320 mL, 7.6 mol) and cyclopropyl amine (432g, 7.6 mol). The resulting solution was refluxed for lOh. The reaction was cooled to 0C, and the solid was collected by filtration. The filter cake was washed with cold ethanol (2x500 mL) to give compound 6. The mother liquor was concentrated and partitioned between water (1000 mL) and ethyl acetate (1000 mL). The aqueous layer was extracted with ethyl acetate (2x500mL), dried over MgS04, filtered, and concentrated to give a second batch of product (total: 650 g, 96%). A suspension of compound 6 (650g, 3.65mol) and 10% Pd/C (50% water; 163 g) in EtOH (7 L) was hydrogenated at 50 psi H2 for 16 h at room temperature. The suspension was filtered through Celite and concentrated. The residue was dried in vacuo to provide compound 7 (490 g, 90.6%). To a solution of compound 7 (490 g, 3.29 mol) in CH3CN (4 L) at 0C was added carbonyldiimidazole (CDI) (559 g, 3.45 mol, 1.05eq.), and the resulting mixture was warmed to room temperature and stirred for 16 h at room temperature. The precipitate was collected by filtration and the solid was washed with cold CH3CN (2 X 1000 mL). The solid was dried in vacuo to give fragment CI . (450 g, 78.2%). m/z = 176 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.84 - 0.91 (m, 2 H), 0.98 - 1.06 (m, 2 H), 2.89 (tt, J=7.0, 3.5 Hz, 1 H), 7.18 (d, J=5.5 Hz, 1 H), 8.16 (s, 1 H), 8.19 (d, J=5.5 Hz, 1 H), 10.98 (br. s., 1 H).
With palladium 10% on activated carbon; hydrogen; In ethanol; under 2585.81 Torr; for 2.0h; A solution of intermediate 10a3 (3.8 g, 21 mmol) and Pd/C 10% (760 mg) in EtOH (32 mL) is stirred under hydrogen atmosphere at 50 psi for 2 h. The catalyst is filtrated through Celite. The filtrate is evaporated under reduced pressure to afford intermediate 10a4.
With palladium 10% on activated carbon; hydrogen; In ethanol; at 30℃; under 2585.81 Torr; To a solution of N-cyclopropyl-3-nitropyridin-4-amine (100 g, 0.560 mol) in EtOH (800 mL) was added 10% Pd/C (8 g). The mixture was stirred under 50 psi of H2 at 30 C overnight. The catalyst was filtered, and the filtrate was concentrated to afford N4-cyclopropylpyridine-3,4- diamine. 1H NMR (400 MHz, DMSO- d6): 57.70- 7.58 (m, 2 H), 6.60 (d, J= 7.2 Hz, 1H), 5.85 (s, 1 H), 4.49 (s, 2 H), 2.43- 2.41 (m, 1H), 0.71- 0.68 (m, 2 H), 0.40- 0.38 (m, 2 H). MS (El) m/z: 150 [M+H]+.

  • 2
  • [ 31872-62-5 ]
  • [ 765-30-0 ]
  • [ 380605-28-7 ]
YieldReaction ConditionsOperation in experiment
72% With N-ethyl-N,N-diisopropylamine; In ethanol; for 3h;Reflux; Step 1: Synthesis of N-cyclopropyl-3-nitropyridin-4-amine 5-b4- Methoxy-3-nitropyridine 5-a (CAS 31872-62-5) (200 g, 1300 mmol), cyclopropylamine (CAS 765-30-0) (185.5 g, 3250 mmol) and DIEA (CAS 7087-68-5) (336 g, 2600 mmol) in dry ethanol (800 mL) were refluxed for 3 hours. The mixture was cooled to 0°C. The solid was collected by filtration. The filter cake was washed with cold ethanol (150 mL). The solid was dried to afford compound 5-b as a white powder (167 g, 72percent).
72% With N-ethyl-N,N-diisopropylamine; In ethanol; for 3h;Reflux; <strong>[31872-62-5]4-methoxy-3-nitropyridine</strong> 7-a (CAS 31872-62-5) (200 g, 1300 mmol), cyclopropyl- amine (185.5 g, 3250 mmol) and diisopropyl ethyl amine (336 g, 2600 mmol) in dry ethanol (800 mL) were refluxed for 3 hours. The mixture was cooled to 0°C. The solid was collected by filtration. The filter cake was washed with cold ethanol (150 mL). The solid was dried to afford the title compound 7-b (167 g, 72percent yield) as a white powder.
72% With N-ethyl-N,N-diisopropylamine; In ethanol; for 3h;Reflux; Scheme 5: Synthesis of l-cyclopropyl-lH-imidazo[4,5-c]pyridin-2(3H)-one (5-d) Step 1: Synthesis of N-cyclopropyl-3-nitropyridin-4-amine (5-b)<strong>[31872-62-5]4-Methoxy-3-nitropyridine</strong> 5-a (CAS 31872-62-5) (200 g, 1300 mmol), cyclopropyl- amine (CAS 765-30-0) (185.5 g, 3250 mmol) and DIEA (CAS 7087-68-5) (336 g, 2600 mmol) in dry ethanol (800 mL) was refluxed for 3 hours. The mixture was cooled to 0°C. The solid was collected by filtration. The filter cake was washed with cold ethanol (150 mL). The solid was dried to afford compound 5-b as a white powder (167 g, 72percent).
72% With N-ethyl-N,N-diisopropylamine; In ethanol; for 3h;Reflux; The mixture of <strong>[31872-62-5]4-methoxy-3-nitropyridine</strong> 10-a (200 g, 1300 mmol, CAS 31872-62-5), cyclopropylamine (185.5 g, 3250 mmol) and diisopropyl ethyl amine (336 g, 2600 mmol) in dry ethanol (800 mL) was refluxed for 3 hours. The mixture was cooled to 0°C. The solid was collected by filtration. The filter cake was washed with cold ethanol (150 mL). The solid was dried to afford the title compound 10-b as a white powder (167 g, 72percent).
72% With N-ethyl-N,N-diisopropylamine; In ethanol; for 3h;Reflux; <strong>[31872-62-5]4-methoxy-3-nitropyridine</strong> 7-a (CAS 31872-62-5) (200 g, 1300 mmol), cyclopropyl-amine (185.5 g, 3250 mmol) and diisopropyl ethyl amine (336 g, 2600 mmol) in dry ethanol (800 mL) were refluxed for 3 hours. The mixture was cooled to 0° C. The solid was collected by filtration. The filter cake was washed with cold ethanol (150 mL). The solid was dried to afford the title compound 7-b (167 g, 72percent yield) as a white powder.
In ethanol; Cyclopropyl-(3-nitro-pyridin-4-yl)-amine A solution of <strong>[31872-62-5]4-methoxy-3-nitropyridine</strong> (7.71 g, 50 mmol) and cyclopropylamine (7.14 g, 125 mmol) in EtOH (20 mL) was heated at 80° C. in a sealed tube for 2 h. The solvent was evaporated to give cyclopropyl-(3-nitro-pyridin-4-yl)-amine as a yellow solid. 1H NMR (CD3OD) delta: 0.72-0.75 (m, 2 H), 0.99-1.03 (m, 2 H), 2.63-2.68 (m, 1 H), 7.19 (d, J=6.2 Hz, 1 H), 8.26 (b, 1 H), 8.35 (d, J=6.2 Hz, 1 H), 9.22 (s, 1 H); IR (KBr, cm-1): 3369, 1613, 1560, 1515, 1406, 1254, 1195, 1039, 881, 846, 769, 545; MS m/e 180 (MH+).
With N-ethyl-N,N-diisopropylamine; In ethanol; for 3h;Reflux; A solution of 10a1 (4 g, 26 mmol) (Molekula), cyclopropylamine 10a2 (4.5 ml_, 64.9 mmol) (Avra) and N, N-diisopropylethylamine (8.9 ml_, 54 mmol) in EtOH (15 mL) is refluxed for 3 h. The reaction mixture is cooled to 0QC and the solid in suspension is collected by filtration. The solid obtained is washed with cold EtOH to afford intermediate 10a3.

 

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