Triethylamine → Isoquinoline-1-carboxylic acid [2-((S)-2-imidazol-1-yl-1-pyridin-3-yl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide

HRID 496430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 496430
[NH2:1][C:2]1[C:11]([O:12][C@@H:13](C2C=CC=CC=2)[CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:26].[C:27]1([C:37]([OH:39])=O)[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][N:28]=1.CN(C(ON1N=N[C:50]2[CH:51]=[CH:52][CH:53]=[N:54][C:49]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl>[N:15]1([CH2:14][C@H:13]([C:52]2[CH:53]=[N:54][CH:49]=[CH:50][CH:51]=2)[O:12][C:11]2[CH:10]=[CH:9][C:8]3[C:7](=[O:26])[CH2:6][CH2:5][CH2:4][C:3]=3[C:2]=2[NH:1][C:37]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][N:28]=2)=[O:39])[CH:19]=[CH:18][N:17]=[CH:16]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 68092Isoquinoline-1-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 600298675-Amino-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

Produkt 1

HCID 60029904Isoquinoline-1-carboxylic acid [2-((S)-2-imidazol-1-yl-1-pyridin-3-yl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl]-amideAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of 5-amino-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (100 mg, 0.287 mmol), 1-isoquinoline carboxylic acid (60 mg, 0.344 mmol), and HATU (131 mg, 0.344 mmol) was added CH2Cl2 (3 mL) and Et3N (48 μL, 0.344 mmol). The reaction was stirred at RT for 5 h. The mixture was diluted with CH2Cl2 and washed with H2O, saturated aqueous NaHCO3 and brine, dried over Na2SO4, and concentrated to give a foam/oil. Purification by chromatography (SiO2, 5-8% MeOH/CH2Cl2) afforded the title compound as a foam (114 mg, 0.226 mmol, 79%). The structure was confirmed by NMR and mass spectrometry. MS m/z 504 (M++H).

Aufarbeitung

  1. washwashed with H2O, saturated aqueous NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give a foam/oil
  5. customPurification by chromatography (SiO2, 5-8% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-ea913423abb44ab2a9d6650e2c72d9e8
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943183B2

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