HCID 16016024, compound → HCID 25255971, compound

HRID 1950842Notes

Reaction equation

HRID 1950842 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[C:16]([N+:26]([O-])=O)[CH:15]=2)[O:11][N:10]=1>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[C:16]([CH:15]=2)[NH2:26])[O:11][N:10]=1

Participants

3

Reactant 1

HCID 16016024HCID 16016024, compound

Product 1

HCID 25255971HCID 25255971, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Stannous chloride dihydrate (147.53 mg; 0.65 mmol; 5 eq.) was added to a solution of example 2 (50 mg; 0.13 mmol; 1 eq.) in EtOH (10 mL), and the reaction mixture was stirred at 70° C. for 3 hours. After cooling, the solution was partitioned between ethyl acetate and aqueous NaHCO3. The organic layer was washed four times with brine, dried over magnesium sulfate and concentrated in vacuo to give a yellow solid. The latter was triturated in Et2O and filtrated to afford the title compound (38 mg, 82%) as a pale yellow solid.

Workup

  1. temperatureAfter cooling
  2. customthe solution was partitioned between ethyl acetate and aqueous NaHCO3
  3. washThe organic layer was washed four times with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a yellow solid
  7. customThe latter was triturated in Et2O
  8. filtrationfiltrated

Sources & evidence

ORD record
ord-365d31e2a36e483ea86dba9c02271c37
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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