Hydrochloric Acid → (3,5-Dibromo-4-methoxy-phenyl)-(7-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

HRID 1943667ノート

反応式

HRID 1943667 の反応式
[CH3:1][C:2]1[CH:11]=[N:10][C:5]2[O:6][CH2:7][CH2:8][NH:9][C:4]=2[CH:3]=1.[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([Br:24])[C:21]=1[O:22][CH3:23])[C:16](Cl)=[O:17].C(N(CC)CC)C.Cl>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([C:16]([N:9]2[CH2:8][CH2:7][O:6][C:5]3[N:10]=[CH:11][C:2]([CH3:1])=[CH:3][C:4]2=3)=[O:17])[CH:19]=[C:20]([Br:24])[C:21]=1[O:22][CH3:23]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 235576307-methyl-1H,2H,3H-pyrido[2,3-b][1,4]oxazineHCID 337796303,5-Dibromo-4-methoxybenzoyl chloride

生成物 1

HCID 44608222(3,5-Dibromo-4-methoxy-phenyl)-(7-methyl-2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone収率 91.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In a 10 ml flask, 7-methyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (79 mg, 0.52 mmol) and 3,5-dibromo-4-methoxy-benzoyl chloride (259 mg, 0.79 mmol) were dissolved in dichloromethane (2 ml). Triethylamine (0.22 ml, 1.58 mmol) was added thereto and then stirred at room temperature for 2 hours. After neutralizing with 1N hydrochloric acid solution, the mixture was extracted with dichloromethane and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of methanol:dichloromethane=1:30. The fractions containing the product were collected and evaporated to obtain white solid (210 mg, 90%).

後処理

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with a solvent of methanol
  6. additionThe fractions containing the product
  7. customwere collected
  8. customevaporated

出典と根拠

ORDレコード
ord-1767991662b947719c8c82fbf9efadcb
出典データセット
uspto-grants-2013_03
特許番号
US08394792B2

反応ノート

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