Triethylamine → N-(4-methoxy-3-pyridyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole 3-carboxamide

HRID 1870490

反応式

HRID 1870490 の反応式
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][CH:5]=[C:4]([C:11]([OH:13])=O)[C:3]1=2.C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][CH3:26])=O.CO[C:29]1C=C[C:32]([NH2:35])=[CH:31][N:30]=1.[Cl-].[NH4+]>CN(C)C=O>[CH3:22][O:24][C:25]1[CH:26]=[CH:29][N:30]=[CH:31][C:32]=1[NH:35][C:11]([C:4]1[C:3]2[C:2](=[O:1])[CH2:10][CH2:9][CH2:8][C:7]=2[NH:6][CH:5]=1)=[O:13]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 811216-Methoxy-3-pyridinylamineHCID 153376324-Oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid

生成物 1

HCID 18696549N-(4-methoxy-3-pyridyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole 3-carboxamide収率 19.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a stirring solution of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (179 mg, 1 mmol) and triethylamine (293 μl, 2.1 mmol) in N,N-dimethylformamide (3 mL) at 0° C. was added ethyl chloroformate (191 μl, 2 mmol). After stirring an additional 30 minutes, a solution of 2-methoxy-5-amino-pyridine (216 mg, 2 mmol) in N,N-dimethylformamide (3 mL) was added. The reaction mixture was allowed to stir for an additional 75 minutes, then poured into saturated aqueous ammonium chloride and extracted 2× with ethyl acetate. The combined organic layers were washed with water, dried over magnesium sulfate, filtered, and concentrated in vacua. To the residue was added aqueous 5N sodium hydroxide (5 mL) and ethyl alcohol (1 mL), then heated at reflux for 1 hour. After cooling in an ice water bath, the reaction mixture was poured into saturated aqueous ammonium chloride and extracted 2× with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, concentrated in vacua, and the residue recrystallized from ethyl acetate to give N-(4-methoxy-3-pyridyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole 3-carboxamide (56 mg); m. p. 209-210° C. (Compound 1).

後処理

  1. stirringto stir for an additional 75 minutes
  2. extractionextracted 2× with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacua
  7. additionTo the residue was added aqueous 5N sodium hydroxide (5 mL) and ethyl alcohol (1 mL)
  8. temperatureheated
  9. temperatureat reflux for 1 hour
  10. temperatureAfter cooling in an ice water bath
  11. additionthe reaction mixture was poured into saturated aqueous ammonium chloride
  12. extractionextracted 2× with ethyl acetate
  13. dry with materialThe combined organic layers were dried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated in vacua
  16. customthe residue recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-3e38bf07d7904bc08b04577813a18035
出典データセット
uspto-grants-2000_08
特許番号
US06096887

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