Triethylamine → 2-(2-t-Butyl-7-chloro-5-fluorobenzoxazol-4-yl)-5-trifluoromethylpyridazin-3-one

HRID 1368027Notes

Reaction equation

HRID 1368027 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:9])[CH:5]=[C:4]([F:10])[C:3]=1[N:11]1[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=[N:12]1.[CH3:22][C:23]([CH3:28])([CH3:27])[C:24](Cl)=[O:25].C(N(CC)CC)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=C(C)C=1>[C:16]([O-:17])(=[O:25])[CH3:15].[CH3:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5].[C:23]([C:28]1[O:8][C:7]2[C:6]([Cl:9])=[CH:5][C:4]([F:10])=[C:3]([N:11]3[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=[N:12]3)[C:2]=2[N:1]=1)([CH3:27])([CH3:24])[CH3:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 185196212-(2-Amino-4-chloro-6-fluoro-3-hydroxyphenyl)-5-trifluoromethylpyridazin-3-one

Product 2

HCID 185196132-(2-t-Butyl-7-chloro-5-fluorobenzoxazol-4-yl)-5-trifluoromethylpyridazin-3-oneHCID 22139250Acetate hexane

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

Step 4 Under nitrogen atmosphere 2-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-5-trifluoromethylpyridazin-3-one from step 3, trimethylacetyl chloride (0.17 g), triethylamine (0.14 g) and pyridinium p-toluenesulfonate in m-xylene(30 ml) was heated at reflux temperature overnight. The mixture was allowed to cool to ambient temperature and partitioned between ethyl acetate and brine. The organic phase was dried over anhydrous sodium sulfate and concentrated to an oil. The crude product was purified by column chromatography on silica gel eluted with ethyl. acetate-hexane (1:8) to afford 2-(2-t-butyl-7-chloro-5-fluorobenzoxazol-4-yl)-5-trifluoromethylpyridazin-3-one (0.26 g) as a pale yellow solid.

Workup

  1. temperatureat reflux temperature overnight
  2. custompartitioned between ethyl acetate and brine
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated to an oil
  5. customThe crude product was purified by column chromatography on silica gel
  6. washeluted with ethyl

Sources & evidence

ORD record
ord-2aaaeb5e0dfe4fd58b3687276d41dd68
Source dataset
uspto-grants-2003_06
Patent number
US06573218B1

Reaction notes

Loading…