Potassium Carbonate → HCID 67498091、化合物

HRID 74228ノート

反応式

HRID 74228 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-])=O.C(=O)([O-])[O-].[K+].[K+].[CH:26]1([CH2:29][NH2:30])[CH2:28][CH2:27]1.[H][H]>C(O)C.[C].[Pd].O>[CH:26]1([CH2:29][NH:30][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:9][C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[N:12]=3)=[CH:4][C:3]=2[NH2:17])[CH2:28][CH2:27]1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 75646CyclopropanemethanamineHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361、化合物

生成物 1

HCID 67498091HCID 67498091、化合物収率 44%

試薬・触媒・溶媒 3

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added potassium carbonate (176 mg, 1.28 mmol) and cyclopropylmethylamine (176 mg, 1.28 mmol), and this was heated to reflux for 7 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered, washed with water and then dried. To a tetrahydrofuran solution (5 mL) of the crystals obtained was added 10% palladium-carbon (50 mg). A hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 6 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (142 mg, 44% yield).

後処理

  1. temperaturethis was heated
  2. temperatureto reflux for 7 hours
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customTo a tetrahydrofuran solution (5 mL) of the crystals obtained
  7. filtrationthis was filtered through Celite
  8. concentrationthe filtrate was concentrated
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-521c6c83bab1436a94260102940597ae
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

反応ノート

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