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

HRID 1368027노트

반응식

HRID 1368027 반응식
[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]

참가 물질

7

반응물 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

생성물 2

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

시약·촉매·용매 1

HCID 7929M-Xylene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2aaaeb5e0dfe4fd58b3687276d41dd68
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06573218B1

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