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

HRID 1368027ノート

反応式

HRID 1368027 の反応式
[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]

参加物

7

反応物 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

生成物 2

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

試薬・触媒・溶媒 1

HCID 7929M-Xylene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2aaaeb5e0dfe4fd58b3687276d41dd68
出典データセット
uspto-grants-2003_06
特許番号
US06573218B1

反応ノート

読み込み中…