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Piperidine → N-(4-tert-butylbenzyl)-2,5-dimethyl-1,8-naphthyridine-3-carboxamide

HRID 1961472
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HRID 1961472 반응식
[C:1]([C:5]1[CH:18]=[CH:17][C:8]([CH2:9][NH:10][C:11](=[O:16])[CH2:12][C:13](=O)[CH3:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:19][C:20]1[N:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:21]=1[CH:22]=O.N1CCCCC1.CCOC(C)=O>CCO>[C:1]([C:5]1[CH:18]=[CH:17][C:8]([CH2:9][NH:10][C:11]([C:12]2[C:13]([CH3:14])=[N:19][C:20]3[C:21]([CH:22]=2)=[C:24]([CH3:28])[CH:25]=[CH:26][N:27]=3)=[O:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

반응물 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 641277472-Amino-4-methylpyridine-3-carbaldehydeHCID 86661979N-(4-tert-butylbenzyl)-3-oxobutanamide

생성물 1

HCID 66632776N-(4-tert-butylbenzyl)-2,5-dimethyl-1,8-naphthyridine-3-carboxamide

시약·촉매·용매 1

HCID 702Ethanol
용매

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온도
120 °C

실험 절차

In a screw cap pressure tube were N-(4-tert-butylbenzyl)-3-oxobutanamide (94.5 mg, 0.38 mmol), 2-amino-4-methylnicotinaldehyde (52.0 mg, 0.38 mmol) and piperidine (151.0 μl, 1.53 mmol) suspended in EtOH (0.5 ml). The tube was sealed and the mixture heated to 120° C. for 1.5 h. The mixture was allowed to cool. EtOAc was added and the mixture washed with H2O, dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography CH2Cl2/MeOH 96/4 yielding 61.5 mg of the title compound (47%).

후처리

  1. customIn a screw cap pressure tube
  2. customThe tube was sealed
  3. temperatureto cool
  4. washthe mixture washed with H2O
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography CH2Cl2/MeOH 96/4 yielding 61.5 mg of the title compound (47%)

출처 및 근거

ORD 기록
ord-6b9578044c0f45c8889ce1379e8dafb6
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415333B2

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