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Triethylamine → N-[(4-fluorophenyl)-methyl]-4-methyl-2-propyl-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide

HRID 2093714
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HRID 2093714 반응식
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[CH3:41][C:42]1[C:51]2[C:46](=[CH:47][C:48]([C:52]([F:55])([F:54])[F:53])=[CH:49][CH:50]=2)[N:45]=[C:44]([CH2:56][CH2:57][CH3:58])[C:43]=1[C:59](O)=[O:60]>C1COCC1.CC(=O)OCC.CCOC(C)=O.CCCCCC>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:59]([C:43]2[C:44]([CH2:56][CH2:57][CH3:58])=[N:45][C:46]3[C:51]([C:42]=2[CH3:41])=[CH:50][CH:49]=[C:48]([C:52]([F:55])([F:54])[F:53])[CH:47]=3)=[O:60])=[CH:4][CH:3]=1
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참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 665838574-Methyl-2-propyl-7-(trifluoromethyl)quinoline-3-carboxylic acid

생성물 1

HCID 56847882N-[(4-fluorophenyl)-methyl]-4-methyl-2-propyl-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide
수율 76%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 21226206Ethyl acetate hexane용매

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온도
50 °C

실험 절차

311 μl (2.7 mmol) 4-fluorobenzylamine, 941 mg (2.5 mmol) HATU and 1 ml (7.2 mmol) NEt3 were added consecutively to a solution of 740 mg (2.5 mmol) 4-methyl-2-propyl-7-(trifluoromethyl)quinoline-3-carboxylic acid in THF (19 ml) and the mixture was then stirred for 72 h at 50° C. The mixture was then diluted with EA and washed with a 4N aq. NH4CL sol., a 1M aq. Na2CO3 sol. and brine. The organic phase was dried over MgSO4, filtered through silica gel and concentrated in a vacuum. After CC (EtOAc/hexane 1:1) of the residue, 770 mg (1.9 mmol, 76%) N-[(4-fluorophenyl)-methyl]-4-methyl-2-propyl-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide (example 3) was obtained. MS: m/z 405.2 [M+H]+.

후처리

  1. washwashed with a 4N aq. NH4CL sol.
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered through silica gel
  4. concentrationconcentrated in a vacuum

출처 및 근거

ORD 기록
ord-f42e3a17cf1844a4b3f34c85667b1251
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08445512B2

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