Amantadine → 2-(2-(1-Adamantylamino)anilin-5-yl)benzoxazole

HRID 74205

反応式

HRID 74205 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.[Na+].[C:25]12([NH2:35])[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH2:26]1)[CH2:32]2.[H][H]>C(O)C.[C].[Pd].O1CCCC1.O>[C:25]12([NH:35][C:2]3[CH:7]=[CH:6][C:5]([C:8]4[O:9][C:10]5[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=5[N:12]=4)=[CH:4][C:3]=3[NH2:17])[CH2:32][CH:31]3[CH2:30][CH:29]([CH2:28][CH:27]([CH2:33]3)[CH2:26]1)[CH2:34]2

参加物

9

反応物 4

HCID 2130AmantadineHCID 516892Sodium BicarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361、化合物

生成物 1

HCID 674988422-(2-(1-Adamantylamino)anilin-5-yl)benzoxazole収率 16.1%

試薬・触媒・溶媒 4

HCID 178418390HCID 178418390、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran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 sodium hydrogen carbonate (195 mg, 2.32 mmol) and 1-adamantylamine (185 mg, 1.22 mmol), and this was heated to reflux with stirring for 4 hours. After the reaction was complete, this was cooled to room temperature, water was added, and the precipitated crystals were filtered off, washed with water and then dried. The crystals obtained were added to a tetrahydrofuran (5 mL) solution containing 10% palladium-carbon (100 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 (67.0 mg, 16% yield) as brown crystals.

後処理

  1. temperaturethis was heated
  2. temperatureto reflux
  3. filtrationthe precipitated crystals were filtered off
  4. washwashed with water
  5. customdried
  6. customThe crystals obtained
  7. stirringthis was stirred at room temperature for 6 hours
  8. filtrationthis was filtered through Celite
  9. concentrationthe filtrate was concentrated
  10. customThe residue obtained
  11. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-017b0ca703ea443186c20c805724ba80
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

関連ノート

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