Isonicotinic Acid → 1-Tert-butoxycarbonyl-4-(pyridin-4-ylcarbamoyl)piperazine

HRID 49778ノート

反応式

HRID 49778 の反応式
[N:1]1[CH:6]=[CH:5][C:4](C(O)=O)=[CH:3][CH:2]=1.C([N:12]([CH2:15]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][N:44]([C:15](=[O:24])[NH:12][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:35])[CH3:36]

参加物

7

反応物 4

HCID 5922Isonicotinic AcidHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 199401P,P-Diphenylphosphinic azide

生成物 1

HCID 98395131-Tert-butoxycarbonyl-4-(pyridin-4-ylcarbamoyl)piperazine

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of pyridine-4-carboxylic acid (1.0 g) and triethylamine (1.2 ml) in toluene (20 ml) was added diphenylphosphoryl azide (1.75 ml) at ambient temperature. The resulting mixture was heated to reflux for 30 minutes and cooled to 0° C. To the mixture was added 1-tert-butoxycarbonylpiperazine (1.51 g), and the mixture was allowed to heat to 90° C. for 1 hour. After cooling to ambient temperature, the reaction mixture was taken up into ethyl acetate, washed in turn with water and brine, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was chromatographed on silica gel (150 ml) eluting with 0-7% methanol in dichloromethane. Trituration with a mixture of diisopropyl ether and ethanol gave 1-tert-butoxycarbonyl-4-(pyridin-4-ylcarbamoyl)piperazine (0.66 g).

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperatureto heat to 90° C. for 1 hour
  4. temperatureAfter cooling to ambient temperature
  5. washwashed in turn with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was chromatographed on silica gel (150 ml)
  9. washeluting with 0-7% methanol in dichloromethane
  10. additionTrituration with a mixture of diisopropyl ether and ethanol

出典と根拠

ORDレコード
ord-9af73983acea4e1ea6cc090fbf6c332f
出典データセット
uspto-grants-2004_03
特許番号
US06710043B1

反応ノート

読み込み中…