3-Methoxyaniline → HCID 68897788, compound

HRID 900319Notes

Reaction equation

HRID 900319 reaction equation
[CH2:1]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[C:16](SC)=[N:17][CH:18]=[N:19]3)[CH2:9][C@@H:8]1[C:26]([O:28][CH3:29])=[O:27])=[O:6])[CH:2]=[CH2:3].[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][CH:38]=1)[NH2:35]>CC#N.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[C:16]([NH:35][C:34]2[CH:36]=[CH:37][CH:38]=[C:32]([O:31][CH3:30])[CH:33]=2)=[N:17][CH:18]=[N:19]3)[CH2:9][C@@H:8]1[C:26]([O:28][CH3:29])=[O:27])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 108243-MethoxyanilineHCID 68900372HCID 68900372, compound

Product 1

HCID 68897788HCID 68897788, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 15B (453 mg, 1.05 mmol), 3-methoxyaniline (142.5 mg, 1.16 mmol) in CH3CN (25 ml) was added AgNO3 (197 mg, 1.16 mmol). The mixture was heated at 70° C. for 30 min. After cooling to room temperature, the solid was removed by filtration through a pad of Celite and the filtrate was concentrated in vacuo. The residue was taken into with water, treated with saturated NaHCO3 and extracted with EtOAc (×3). The combined extracts were dried over anhydrous Na2SO4. Concentration in vacuo gave 644 mg of crude 15C as an oil, which was used in next step without further purification. The compound has an analytical HPLC retention time=2.259 min (Chromolith SpeedROD column 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA over 4 minutes, 4 mL/min, monitoring at 254 nm) and a LC/MS M++H=506+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solid was removed by filtration through a pad of Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. additiontreated with saturated NaHCO3
  5. extractionextracted with EtOAc (×3)
  6. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-a2152741b20f4f6a9f5674a207a9bd33
Source dataset
uspto-grants-2008_04
Patent number
US07358256B2

Reaction notes

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