Dimethylformamide → 4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-nicotinic acid methyl ester

HRID 1245739

반응식

HRID 1245739 반응식
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1Cl.[CH3:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1N(C)C.[C:29](=O)([O-])[O-].[K+].[K+].C[N:36]([CH:38]=O)C>[Cu]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1[NH:36][C:38]1[C:25]([CH3:21])=[CH:26][C:27]([CH3:29])=[CH:28][C:20]=1[CH3:19]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11869N,N,2-TrimethylanilineHCID 248068762-Chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl ester

생성물 1

HCID 695872624-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-nicotinic acid methyl ester

시약·촉매·용매 1

HCID 23978Copper촉매

실험 절차

A mixture of 2-chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl ester, trimethylaniline, potassium carbonate, copper in DMF was heated at reflux. The mixture was quenched with ammonium chloride and stirred for 20 min, filtered through celite and washed with ethyl acetate. The filtrate was extracted with ethyl acetate. The organic layer was separated, dried and concentrated to dryness. The residue was purified through silica gel column chromatography using 2% methanol in chloroform as eluent to give the title compound as a solid.

후처리

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe mixture was quenched with ammonium chloride
  4. filtrationfiltered through celite
  5. washwashed with ethyl acetate
  6. extractionThe filtrate was extracted with ethyl acetate
  7. customThe organic layer was separated
  8. customdried
  9. concentrationconcentrated to dryness
  10. customThe residue was purified through silica gel column chromatography

출처 및 근거

ORD 기록
ord-4f03e17beaa84580b5c35b5b6b64d128
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125880B1

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