Trifluoroacetic acid → HCID 15949773, compound

HRID 548729Notes

Reaction equation

HRID 548729 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1([CH3:46])[N:14](COC)[C:13](=[O:18])[C:12]2[CH:19]=[CH:20][C:21]([O:23][C:24]3[CH:25]=[C:26]([CH:37]=[C:38]([O:40][C@H:41]4[CH2:45][CH2:44][O:43][CH2:42]4)[CH:39]=3)[C:27]([NH:29][C:30]3[CH:35]=[N:34][C:33]([CH3:36])=[CH:32][N:31]=3)=[O:28])=[CH:22][C:11]=2[O:10]1>C(Cl)Cl>[CH3:8][C:9]1([CH3:46])[NH:14][C:13](=[O:18])[C:12]2[CH:19]=[CH:20][C:21]([O:23][C:24]3[CH:25]=[C:26]([CH:37]=[C:38]([O:40][C@H:41]4[CH2:45][CH2:44][O:43][CH2:42]4)[CH:39]=3)[C:27]([NH:29][C:30]3[CH:35]=[N:34][C:33]([CH3:36])=[CH:32][N:31]=3)=[O:28])=[CH:22][C:11]=2[O:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15949692HCID 15949692, compound

Product 1

HCID 15949773HCID 15949773, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 mL) was added to 3-({2,2-dimethyl-3-[(methyloxy)methyl]-4-oxo-3,4-dihydro-2H-1,3-benzoxazin-7-yl}oxy)-N-(5-methylpyrazin-2-yl)-5-[(3S)-tetrahydrofuran-3-yloxy]benzamide (54 mg, 0.1 mmol) and stirred at RT for 48 hours. DCM was added and the solvent removed in vacuo. Ethyl acetate (50 mL) was added and the mixture washed with water (50 mL), saturated sodium bicarbonate solution (50 mL), brine (50 mL), dried (MgSO4), and reduced in vacuo. The crude oil was chromatographed on silica, eluting with 0-2.5% methanol in ethyl acetate, to give the desired compound as a white foam (14 mg).

Workup

  1. customthe solvent removed in vacuo
  2. additionEthyl acetate (50 mL) was added
  3. washthe mixture washed with water (50 mL), saturated sodium bicarbonate solution (50 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customThe crude oil was chromatographed on silica
  6. washeluting with 0-2.5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-d14c462e91cc45b69739374dfe9bf7bd
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

Loading…