Hydrochloric Acid → HCID 58103902, compound

HRID 1627029Notes

Reaction equation

HRID 1627029 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][N:16]4[C:19]([CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:20][N:21]=[C:15]4[C:14]=3N)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N([O-])=O.[Na+].[NH4+].[OH-].O.[ClH:35]>Cl[Cu]>[Cl:35][C:14]1[C:15]2[N:16]([C:19]([CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:20][N:21]=2)[CH:17]=[CH:18][C:13]=1[N:10]1[CH2:11][CH2:12][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 58103930HCID 58103930, compoundHCID 86589665Water ammonium hydroxide

Product 1

HCID 58103902HCID 58103902, compound

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Conditions

Temperature
0 °C

Procedure

A solution of intermediate D50 (0.05 g, 0.134 mmol) in chlorhydric acid 12N was stirred at room temperature for 10 min. Then after cooling to 0° C., NaNO2 (0.184 mg, 2.671 mmol) was slowly added, followed by CuCl (104.024 mg, 0.14 mmol). The reaction mixture was then stirred at room temperature for 16 h. The reaction was further heated at 80° C. for 90 min., cooled, poured into a mixture of NH4OH:H2O 1:1 and then extracted with DCM. The combined organic phase was dried (Na2SO4) and the solvent evaporated in vacuo. The residue was purified by column chromatography (silica gel; starting from DCM/EtOAc up to 10% as eluent). The desired fractions were collected and evaporated in vacuo. The residue thus obtained was triturated with diisopropylether to yield E51 (19 mg, 36%) as a brown solid

Workup

  1. temperatureThe reaction was further heated at 80° C. for 90 min.
  2. temperaturecooled
  3. extractionextracted with DCM
  4. dry with materialThe combined organic phase was dried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified by column chromatography (silica gel
  7. customThe desired fractions were collected
  8. customevaporated in vacuo
  9. customThe residue thus obtained
  10. customwas triturated with diisopropylether
  11. customto yield E51 (19 mg, 36%) as a brown solid

Sources & evidence

ORD record
ord-80cbe7248f9e49488da4135512aac373
Source dataset
uspto-grants-2014_07
Patent number
US08785486B2

Reaction notes

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