Triethylamine → HCID 15027620, compound

HRID 1090641Notes

Reaction equation

HRID 1090641 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].C(N(CC)CC)C.O=[S:22]1[CH2:27][CH2:26][CH2:25][N:24]2[C:28](=[O:42])[N:29]([CH2:39][CH2:40][CH3:41])[C:30](=[O:38])[C:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[C:23]12>C(Cl)Cl>[OH:4][CH:27]1[S:22][C:23]2=[C:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:30](=[O:38])[N:29]([CH2:39][CH2:40][CH3:41])[C:28](=[O:42])[N:24]2[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 15027579HCID 15027579, compound

Product 1

HCID 15027620HCID 15027620, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Trifluoroacetic anhydride (3.78 g) and triethylamine (1.82 g) were added to a solution of 1-oxo-9-phenyl-7-propyl-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione (4 g) in methylene chloride (60 ml) and the mixture was stirred at 40° C. for 60 hours. The reaction solution was evaporated to dryness, and the residue was dissolved in methylene chloride-H2O. Then, the organic layer was washed with a saturated aqueous sodium bicarbonate. After drying, the organic solution was concentrated, and the resulting residue was purified by column chromatography on silica gel. The resulting crude crystals were recrystalized from methylene chloride-isopropyl ether to give colorless needles (3.1 g, 78%).

Workup

  1. customThe reaction solution was evaporated to dryness
  2. dissolutionthe residue was dissolved in methylene chloride-H2O
  3. washThen, the organic layer was washed with a saturated aqueous sodium bicarbonate
  4. customAfter drying
  5. concentrationthe organic solution was concentrated
  6. customthe resulting residue was purified by column chromatography on silica gel
  7. customThe resulting crude crystals were recrystalized from methylene chloride-isopropyl ether

Sources & evidence

ORD record
ord-a5b2e8188de648df9cb4e8a85ff97324
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

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