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Triethylamine → 7-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid (carbamoyl-phenyl-methyl)-amide

HRID 51928
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 51928
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]([NH:17][C:18]3[CH:27]=[C:26]4[C:21]([CH:22]=[C:23]([C:28]([OH:30])=O)[CH:24]=[N:25]4)=[CH:20][CH:19]=3)=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.C1([NH:39][CH2:40][C:41]([NH2:43])=[O:42])C=CC=CC=1.Cl.CN(C)CCCN=C=NCC.ON1[C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][C:60]=2N=N1.C(N(CC)CC)C>ClCCl>[C:41]([CH:40]([NH:39][C:28]([C:23]1[CH:24]=[N:25][C:26]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[C:18]([NH:17][C:15]([C:10]1[C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:31])([F:1])[F:32])=[CH:8][CH:7]=3)=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:16])[CH:27]=2)=[O:30])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)(=[O:42])[NH2:43]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 102967197-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino)-quinoline-3-carboxylic acidHCID 153703192-(Phenylamino)acetamide

Produkt 1

HCID 10166750
7-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid (carbamoyl-phenyl-methyl)-amide
Ausbeute 42,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

7-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid (100 mg, 0.23 mmol) was combined with phenylglycinamide (34 mg, 0.23 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (53 mg, 0.27 mmol), 1-hydroxybenzotriazole (34 mg, 0.25 mmol), and triethylamine (0.13 ml, 0.92 mmol) in 1.5 ml of dichloromethane. After stirring overnight at ambient temperature, the reaction mixture was diluted with 50 ml of dichloromethane, and the organic phase washed sequentially with water, and brine, and then dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide a residue. This material was purified by preparative thin-layer-chromatography on silica eluting with ethyl acetate. The product containing band was collected and eluted with 5% methanol in ethyl acetate to afford 56 mg of the title compound.

Aufarbeitung

  1. washthe organic phase washed sequentially with water, and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto provide a residue
  6. customThis material was purified by preparative thin-layer-chromatography on silica eluting with ethyl acetate
  7. additionThe product containing band
  8. customwas collected
  9. washeluted with 5% methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ce3b07d0fb4a466e880a4fc27ac04394
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06713489B2

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