Triethylamine → N-[3-(methylaminomethyl)phenyl]-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide

HRID 1180493

반응식

HRID 1180493 반응식
[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:16]([CH2:19]C)[CH2:17][CH3:18])C.ClC(OCC)=O.FC(F)(F)C([N:31](CNC)[C:32]1[CH:37]=C[CH:35]=[CH:34][CH:33]=1)=O.[Cl-].[NH4+]>CN(C)C=O>[CH3:19][NH:16][CH2:17][C:18]1[CH:37]=[C:32]([NH:31][C:11]([C:4]2[C:3]3[C:2](=[O:1])[CH2:10][CH2:9][CH2:8][C:7]=3[NH:6][CH:5]=2)=[O:13])[CH:33]=[CH:34][CH:35]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 153376324-Oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acidHCID 57112434N-trifluoroacetyl-(methylaminomethyl)aniline

생성물 1

HCID 9817695N-[3-(methylaminomethyl)phenyl]-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (100 mg, 0.6 mmol) and triethylamine (0.15 mL, 1.1 mmol) in N,N-dimethylformamide (5 mL) at 0° C. is added ethyl chloroformate (0.1 mL, 1.1 mmol). After stirring an additional 1 hour, 3-(N-trifluoroacetyl-(methylaminomethyl)aniline (0.3 g, 1.3 mmol) is added. The reaction mixture is stirred for 4 hours, then poured into saturated aqueous ammonium chloride and extracted 2× with ethyl acetate. The combined organic layers are washed sequentially with brine, aqueous 2N hydrochloric acid, then brine, dried over sodium sulfate, filtered, and concentrated in vacuo. To the residue is added 15% aqueous potassium bicarbonate (5 mL) and methyl alcohol (3 mL), then heated at reflux for 3 hours. After cooling, the reaction mixture is extracted with ethyl acetate, the organic layer dried over sodium sulfate, filtered, and concentrated in vacuo to give N-[3-(methylaminomethyl)phenyl]-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide. m.p. 130-132° C.

후처리

  1. stirringThe reaction mixture is stirred for 4 hours
  2. extractionextracted 2× with ethyl acetate
  3. washThe combined organic layers are washed sequentially with brine, aqueous 2N hydrochloric acid
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionTo the residue is added 15% aqueous potassium bicarbonate (5 mL) and methyl alcohol (3 mL)
  8. temperatureheated
  9. temperatureat reflux for 3 hours
  10. temperatureAfter cooling
  11. extractionthe reaction mixture is extracted with ethyl acetate
  12. dry with materialthe organic layer dried over sodium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-56cf6187554e4ed4b9ca1737450ec6fb
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282498B2

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