HCID 25255976, compound → HCID 68775324, compound

HRID 336276Notes

Reaction equation

HRID 336276 reaction equation
[F:1][C:2]1([F:30])[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:18][N:17]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][CH3:26])[N:15]=3)=[CH:10][C:9]=2[N+:27]([O-])=O)[CH2:3]1>CCO.C([O-])(O)=O.[Na+]>[F:30][C:2]1([F:1])[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:18][N:17]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][CH3:26])[N:15]=3)=[CH:10][C:9]=2[NH2:27])[CH2:3]1

Participants

4

Reactant 1

HCID 25255976HCID 25255976, compound

Product 1

HCID 68775324HCID 68775324, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

Stannous chloride dihydrate (285 mg; 1.26 mmol; 5 eq.) was added to a solution of Example 12 (105 mg; 0.25 mmol; 1 eq.) in EtOH (20 mL) and the resulting mixture was stirred at 70° C. for 3 hours, then at room temperature for 16 hours. The solution was diluted with sat. aq. NaHCO3 and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (97 mg, 100%) as a yellow solid.

Workup

  1. waitat room temperature for 16 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f419523806eb428abd5b039a889c2731
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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