HCID 25256072, compound → HCID 25256481, compound

HRID 1950853Notes

Reaction equation

HRID 1950853 reaction equation
[F:1][C:2]1([F:33])[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][C:26]([F:29])([F:28])[F:27])[N:15]=3)=[CH:10][C:9]=2[N+:30]([O-])=O)[CH2:3]1>CCO.C([O-])(O)=O.[Na+]>[F:33][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][C:26]([F:27])([F:28])[F:29])[N:15]=3)=[CH:10][C:9]=2[NH2:30])[CH2:3]1

Participants

4

Reactant 1

HCID 25256072HCID 25256072, compound

Product 1

HCID 25256481HCID 25256481, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

Stannous chloride dihydrate (478 mg; 2.13 mmol; 5 eq.) was added to a solution of Example 11 (200 mg; 0.43 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. Purification by column chromatography (c-hexane/ethyl acetate, 70/30) followed by crystallization from n-pentane afforded the title compound as an off-white 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
  6. customPurification by column chromatography (c-hexane/ethyl acetate, 70/30)
  7. customfollowed by crystallization from n-pentane

Sources & evidence

ORD record
ord-28452c7c2f574b4781684c20f9e86720
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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