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[ CAS No. 130473-27-7 ]

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2D
Chemical Structure| 130473-27-7
Chemical Structure| 130473-27-7
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Product Details of [ 130473-27-7 ]

CAS No. :130473-27-7MDL No. :MFCD10697726
Formula : C8H6N2O2 Boiling Point : 471.1°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :162.15Pubchem ID :14644284
Synonyms :

Computed Properties of [ 130473-27-7 ]

TPSA : 66 H-Bond Acceptor Count : 3
XLogP3 : 0.8 H-Bond Donor Count : 2
SP3 : 0.00 Rotatable Bond Count : 1

Safety of [ 130473-27-7 ]

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

Application In Synthesis of [ 130473-27-7 ]

  • Upstream synthesis route of [ 130473-27-7 ]
  • Downstream synthetic route of [ 130473-27-7 ]

[ 130473-27-7 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 130473-26-6 ]
  • [ 130473-27-7 ]
YieldReaction ConditionsOperation in experiment
67% With sodium hydroxide; dihydrogen peroxide In formic acid; water C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid.
The solution is cooled in an ice bath, 30percent aqueous hydrogen peroxide (722 μL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5° C.
The mixture is diluted with H2O, the solid is collected, washed with H2O and is dried to give 522 mg of an off-white solid.
The formate salt is added to 7 mL H2O, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5percent aqueous HCl.
The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67percent yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H).
Example 23(i)
can be obtained by coupling either exo-[2.2.1]-3-Amine or endo-[2.2.1]-3-Amine with C176.
67% With sodium hydroxide; dihydrogen peroxide In formic acid; water C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid.
The solution is cooled to in an ice bath, 30percent aqueous hydrogen peroxide (722 μL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5° C.
The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid.
The formate salt is added to 7 mL water, 3 mL 2N NaOH is added, and the pH is adjusted to 3 with 5percent aqueous HCl.
The precipitate is collected and is dried to afford 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid (C176) (67percent yield). HRMS (FAB) calculated for C8H6N2O2+H: 163.0508, found 163.0507 (M+H)+.
67%
Stage #1: With dihydrogen peroxide In formic acid; water at 5℃;
Stage #2: With sodium hydroxide In water
Stage #3: With hydrogenchloride In water
C174 (500 mg, 3.42 mmol) is dissolved in 1.5 mL formic acid. The solution is cooled to in an ice bath, 30percent aqueous hydrogen peroxide (722 RL, 6.8 mmol) is added drop-wise, and the reaction is stirred 1 h in an ice bath, and allowed to stand overnight at 5C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is added to 7 mL water, 3 mL 2N NAOH is added, and the pH is adjusted to 3 with 5percent aqueous HC1. The precipitate is collected and is dried to afford 1H-pyrrolo [2,3-c] pyridine-5- carboxylic acid (C176 (67percent yield). HRMS (FAB) calculated for CGH6N202+H : 163.0508, found 163.0507 (M+H) +.
67% With dihydrogen peroxide In formic acid; water 1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde (500 mg, 3.42 mmol) is dissolved in 1.5 ml formic acid.
The solution is cooled in an ice bath, is treated drop-wise with 30percent aqueous hydrogen peroxide (722 μL, 6.8 mmol), is stirred 1 h in an ice bath, and allow to stand overnight at 5° C.
The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid.
The formate salt is combined with 7 ml water, is diluted with 3 ml 2N NaOH, and the pH is adjusted to 3 with 5percent aqueous HCl.
The precipitate is collected and is dried to give 370 mg (67percent) of 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. HRMS (FAB) calcd for C8H6N2O2+H: 163.0508, found 163.0507 (M+H)+.

Reference: [1] Tetrahedron, 1990, vol. 46, # 9, p. 3245 - 3266
[2] Synthesis, 1993, # 3, p. 295 - 297
[3] Patent: US2003/153595, 2003, A1,
[4] Patent: US2003/45540, 2003, A1,
[5] Patent: WO2004/39815, 2004, A2, . Location in patent: Page 58
[6] Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4425 - 4436
[7] Patent: US2003/105089, 2003, A1,
  • 2
  • [ 119694-70-1 ]
  • [ 130473-27-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4425 - 4436
[2] Tetrahedron, 1990, vol. 46, # 9, p. 3245 - 3266
[3] Tetrahedron, 1990, vol. 46, # 9, p. 3245 - 3266
  • 3
  • [ 130473-24-4 ]
  • [ 130473-27-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4425 - 4436
[2] Tetrahedron, 1990, vol. 46, # 9, p. 3245 - 3266
  • 4
  • [ 108-47-4 ]
  • [ 130473-27-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4425 - 4436
  • 5
  • [ 5832-38-2 ]
  • [ 130473-27-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4425 - 4436
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