Morpholine → HCID 90357010, 화합물

HRID 55869

반응식

HRID 55869 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 90357010HCID 90357010, 화합물수율 63%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-e5463e04a26a4badb67d0ed2119cd9ca
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433622B2

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