Triethylamine → HCID 59389410, compound

HRID 2357948Notes

Reaction equation

HRID 2357948 reaction equation
C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:21][O:22][C:23]1[N:28]2[N:29]=[C:30]([CH:32]=[N:33]O)[CH:31]=[C:27]2[C:26]([C:35]2[CH:36]([CH3:42])[CH2:37][C:38](=[O:41])[NH:39][N:40]=2)=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:21][O:22][C:23]1[N:28]2[N:29]=[C:30]([C:32]#[N:33])[CH:31]=[C:27]2[C:26]([C:35]2[CH:36]([CH3:42])[CH2:37][C:38](=[O:41])[NH:39][N:40]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 136013274HCID 136013274, compound

Product 1

HCID 59389410HCID 59389410, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.291 mL) and trifluoroaceticanhydride (0.116 mL) were added to a suspension of the compound of Example 344 (63.0 mg) in methylene chloride (6 mL). The mixture was stirred at room temperature for 1 hour. Subsequently, a saturated aqueous sodium bicarbonate solution was added and the mixture was stirred for 30 min. The organic layer was separated and the aqueous layer was extracted with methylene chloride. The combined organic layer was dried over anhydrous magnesium sulfate. Evaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (NH type, methylene chloride:methanol=9:1) afforded the title compound as a pale yellow powder (31.3 mg).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with methylene chloride
  4. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (NH type, methylene chloride:methanol=9:1)

Sources & evidence

ORD record
ord-dc3c35763482425d9b9b5bb8679c8766
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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