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Chemical Structure| 573758-69-7 Chemical Structure| 573758-69-7

Structure of 573758-69-7

Chemical Structure| 573758-69-7

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Product Details of [ 573758-69-7 ]

CAS No. :573758-69-7
Formula : C10H7N3
M.W : 169.18
SMILES Code : N#CC1=NC=C(N)C2=C1C=CC=C2
MDL No. :MFCD13193455
InChI Key :AILGQDQQFHALOG-UHFFFAOYSA-N
Pubchem ID :21875272

Safety of [ 573758-69-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 573758-69-7 ]

* 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 [ 573758-69-7 ]

[ 573758-69-7 ] Synthesis Path-Downstream   1~5

YieldReaction ConditionsOperation in experiment
92% 13D. 4-Aminoisoquinoline-1-carbonitrile Compound 13C (50 mg, 0.16 mmol) was treated with TFA (0.5 mL) for 1 h. The highly colored mixture was partitioned between EtOAc (30 mL) and 1 N NaOH (30 mL). After washing with brine (15 mL), the organic layer was dried (MgSO4) and concentrated under reduced pressure to afford compound 13D (24 mg, 92%) as a yellow solid. HPLC: 99% at 1.09 min (retention time) (Phenomenex C-18, 5 micron column, 4.6*30 mm, eluding with 10-90% aqueous MeOH over 2 min containing 0.1% TFA, 4 mL/min, monitoring at 254 nm). MS (ES+) m/z 170 [M+H]+.
  • 2
  • [ 108-31-6 ]
  • [ 573758-69-7 ]
  • [ 573761-48-5 ]
YieldReaction ConditionsOperation in experiment
263 mg (90%) In acetic acid; A. 4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-isoquinoline-1-carbonitrile (748A) A mixture of compound 470D (200 mg, 1.18 mmol) and maleic anhydride (470 mg, 4.7 mmol) in glacial acetic acid (5 mL) was heated to reflux for 4 hours. After removing the volatiles in vacuo, the residue was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was washed with saturated sodium bicarbonate solution (2*50 mL) and brine (50 mL). After drying over magnesium sulfate, the organic layer was filtered through a 1*5 cm plug of silica gel. The filtrate was concentrated to afford 263 mg (90%) of 748a as an off-white solid. HPLC: 99% at 1.12 min (Phenomenex 5 micron ODS 4.6*30 mm, 10%-90% aqueous methanol over 2 minute gradient with 0.1% TFA, detecting at 254 nm). MS (ES): m/z 250.2 [M+H]+.
  • 3
  • [ 1013-88-3 ]
  • [ 27224-09-5 ]
  • 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl [ No CAS ]
  • [ 573758-69-7 ]
YieldReaction ConditionsOperation in experiment
450 mg (53%) With hydrogenchloride; caesium carbonate;palladium diacetate; In tetrahydrofuran; ethyl acetate; toluene; An alternative route to the synthesis of compound 470D is as follows. A mixture of compound 470B (1.17 g, 5.02 mmol), benzophenone imine (1.05 mL, 6.26 mmol), palladium acetate (25 mg, 0.11 mmol), rac-2,2'-bis(diphenylphosphino)-1,1' binaphthyl (100 mg, 0.161 mmol) and cesium carbonate (2.30 g, 7.06 mmol) in 20 mL of toluene was heated at 100 C. for 20 h. The reaction mixture was diluted with ethyl ether (200 mL) and filtered through Celite. After concentrating the filtrate, the residue was dissolved in 120 mL of THF and treated with 40 mL of 1N HCl. After standing for 2 h at room temperature, the mixture was partitioned between ethyl acetate (150 mL) and 0.25 N NaOH (160 mL). After washing with brine (100 mL), the organic layer was dried over magnesium sulfate. The organic layer was filtered and ~50 g of celite was added to the filtrate. After concentration in vacuo, the powdery residue was purified by flash chromatography on a 5*15 cm silica gel column eluding with 1 L each of 1:1 ethyl acetate:hexane, 6:4 ethyl acetate:hexane and 8:2 ethyl acetate:hexane to give 450 mg (53%) of 470D as a yellow powder.
  • 4
  • [ 573758-64-2 ]
  • [ 573758-69-7 ]
YieldReaction ConditionsOperation in experiment
24 mg (92%) With trifluoroacetic acid; D. 4-Amino-isoquinoline-1-carbonitrile (470D) Compound 470C (50 mg, 0.16 mmol) was treated with trifluoroacetic acid (0.5 mL) for 1 h. The highly colored mixture was partitioned between ethyl acetate (30 mL) and 1N NaOH (30 mL). After washing with brine (15 mL), the organic layer was dried over magnesium sulfate and concentrated in vacuo to afford 24 mg (92%) of compound 470D as a yellow solid. HPLC: 99% at 1.09 min (retention time) (Phenomenex C-18, 5 micron column, 4.6*30 mm, eluding with 10-90% aqueous methanol over 2 min containing 0.1% TFA, 4 mL/min, monitoring at 254 nm). MS (ES+): m/z 170.2 [M+H]+.
  • 5
  • [ 573758-69-7 ]
  • [ 463-71-8 ]
  • [ 1332391-99-7 ]
YieldReaction ConditionsOperation in experiment
In ISOPROPYLAMIDE; at 20.0℃; A mixture of 4-aminoisoquinoline- 1 -carbonitrile (500 mg, 2.95 mmol) andthiophosgene (0.34 mL, 4.44 mmol) in DMA (5 mL) was stirred at room temperature overnight. The mixture was diluted with EtOAc/water. The two layers were separated and the aqueous layer was extracted with EtOAc (3x). The organics were combined, washed with a saturated solution of sodium bicarbonate (2x), dried over sodium sulfate, and evaporated to dryness to afford 553 mg of 4-isothiocyanatoisoquino line- 1 -carbonitrile as an orange oil. 'H NMR (300 MHz, DMSO-de) δ 8.88 (s, 1H), 8.32 (d, 1H), 8.23 (d, 1H), 8.12 (td, 1H), 8.05 (td, 1H).
References:
 

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