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[ CAS No. 686747-19-3 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 686747-19-3
Chemical Structure| 686747-19-3
Structure of 686747-19-3 *Storage: {[proInfo.prStorage]}

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Product Details of [ 686747-19-3 ]

CAS No. :686747-19-3MDL No. :MFCD06204187
Formula : C10H10N2O2 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :190.20Pubchem ID :45089221
Synonyms :

Computed Properties of [ 686747-19-3 ]

TPSA : 68.1 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 2
SP3 : 0.10 Rotatable Bond Count : 2

Safety of [ 686747-19-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 686747-19-3 ]

  • Upstream synthesis route of [ 686747-19-3 ]
  • Downstream synthetic route of [ 686747-19-3 ]

[ 686747-19-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 686747-51-3 ]
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YieldReaction ConditionsOperation in experiment
97% With hydrogen In methanol for 5.00 h; To a solution of 5- NITRO-1 H-INDOLE-3-CARBOXYLIC acid methyl ester (206 mg, 0.940 MMOL) in methanol (40 mL) was added 5percent palladium on carbon (40 mg) and the mixture was stirred under 1 atm H2 for 5h. The mixture was filtered through celite and the filtrate evaporated to yield a brown solid that was used without further purification (173 mg, 97percent), single spot at Rf 0.64 (ethyl ACETATE).APOS;H NMR (D6-DMSO) : 5 11.50 (1H, s, N-H), 7.83 (1H, d, J=3. 2 Hz), 7.17 (1H, d, J=2.0 Hz), 7.14 (1H, d, J=8.4 Hz), 6.56 (1H, dd, J=8.6, 2.2 Hz), 4.77 (2H, s, N-H2), 3.76 (3H, s). To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (124 mg, 0.552 MMOL) in dichloromethane (4 mL) was added pyridine (100 uL, 1.3 MMOL) and the mixture was stirred under N2 for 5 min, after which time 5-AMINO-1H-INDOLE-CARBOXYLIC acid methyl ester (100 mg, 0.526 MMOL) was added. The resulting mixture was stirred for 1.5 h at room temperature, then saturated NAHC03 solution (15 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (NA2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a white solid (129 mg, 65percent), single spot at Rf 0.84 (ethyl acetate). mp 216.8-219. 3°C, [22], HPLC purity 99+percent (tR 2.07 min in 10percent water- ACETONITRILE).APOS;H NMR (D6-DMSO) : 5 11.91 (1H, s), 10.32 (1H, s), 8.03 (1H, d, J=3.0 Hz), 7.82 (1H, d, J=7. 9 Hz), 7.70-7. 67 (2H, m), 7.37-7. 31 (2H, m), 6.95 (1H, dd, J=8.6, 2.0 Hz), 3.77 (3H, s), 2.65 (3H, s). LCMS: 377.09. FAB-MS (MH+, C17H15CIN2O4S) : calcd 378.0441, found 378.0439.
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9875 - 9890
[2] Patent: WO2004/37251, 2004, A1. Location in patent: Page/Page column 111; 112
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Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9875 - 9890
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  • [ 6146-52-7 ]
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Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9875 - 9890
  • 4
  • [ 1058740-61-6 ]
  • [ 686747-19-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9875 - 9890
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