Morpholine → HCID 90357010、化合物

HRID 55869

反応式

HRID 55869 の反応式
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][N:7]=1)=[O:4].[NH:15]1[CH2:20][CH2:19]O[CH2:17][CH2:16]1.[C:21](=O)(O)[O-].[Na+].C([O-])=O.[NH4+]>C1COCC1.C(Cl)Cl>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:15]2[CH2:20][CH2:19][CH2:21][CH2:17][CH2:16]2)=[N:7][CH:8]=1

参加物

7

反応物 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 2723923Ammonium formateHCID 40664452-chloro-N-(5-nitropyridin-2-yl)acetamide

生成物 1

HCID 90357010HCID 90357010、化合物収率 63%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Compound 20 (3.0 g, 13.9 mmol), was dissolved in THF (100 mL). Morpholine (20 mL, 229 mmol) was added and the mixture stirred at reflux for 1 hour. DCM (200 mL) and saturated aqueous sodium bicarbonate solution (200 mL) were added and the layers separated. The organic phase was dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was dissolved in EtOH (200 mL) and 10% Pd/C (wet, ˜300 mg) followed by ammonium formate (880 mg, 14.0 mmol) added. The mixture was stirred at reflux for 1 hour. The mixture was cooled to rt, filtered through celite, washing the precipitate with EtOAc. The collected filtrate was diluted with saturated ammonium bicarbonate solution (100 mL) and the layers separated. The organic phase was dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was triturated with EtOAc-isohexane to afford the title compound as an off-white solid (2.1 g, 63%); (m/z): 237 [MH]+.

後処理

  1. temperatureat reflux for 1 hour
  2. customthe layers separated
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. dissolutionThe residue was dissolved in EtOH (200 mL)
  7. additionadded
  8. stirringThe mixture was stirred
  9. temperatureat reflux for 1 hour
  10. filtrationfiltered through celite
  11. washwashing the precipitate with EtOAc
  12. additionThe collected filtrate was diluted with saturated ammonium bicarbonate solution (100 mL)
  13. customthe layers separated
  14. dry with materialThe organic phase was dried (MgSO4)
  15. filtrationfiltered
  16. customthe solvent evaporated in vacuo
  17. customThe residue was triturated with EtOAc-isohexane

出典と根拠

ORDレコード
ord-e5463e04a26a4badb67d0ed2119cd9ca
出典データセット
uspto-grants-2016_09
特許番号
US09433622B2

関連ノート

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