Diisopropylethylamine → HCID 51051182, Verbindung

HRID 1694383

Reaktionsgleichung

Reaktionsgleichung von HRID 1694383
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17](OC)=[O:18])[CH:10]=[CH:9]2)=[CH:5][CH:4]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:49][C:50]1([C:53]2[CH:62]=[CH:61][C:56]([C:57]([O:59][CH3:60])=[O:58])=[CH:55][CH:54]=2)[CH2:52][CH2:51]1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CCOC(C)=O.CN(C=O)C>[F:23][C:2]([F:1])([F:24])[C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([NH:49][C:50]3([C:53]4[CH:62]=[CH:61][C:56]([C:57]([O:59][CH3:60])=[O:58])=[CH:55][CH:54]=4)[CH2:52][CH2:51]3)=[O:18])[CH:10]=[CH:9]2)=[CH:5][CH:4]=1

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45140209Methyl 4-(1-aminocyclopropyl)benzoateHCID 57434482HCID 57434482, Verbindung

Produkt 1

HCID 51051182HCID 51051182, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 1-[4-(trifluoromethyl)benzyl]-1H-indole-7-carboxylate (30.8 g, 97 mmol), HATU (38.6 g, 101 mmol) and methyl 4-(1-aminocyclopropyl)benzoate (24.9 g, 130 mmol) were added to DMF (483 ml). The solution was cooled in an ice bath and DIPEA (50.6 ml, 290 mmol) was added. The mixture was aged overnight at RT and 500 ml of EtOAc was added. The mixture was then poured into 2 L of NaHCO3 (½ sat.). The layers were cut and the aqueous layer was washed 2 more times with DCM. The combined organic layers were washed with brine and dried with Na2SO4. The solvent was removed and the crude mixture purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d6): δ 9.18 (s, 1H), 7.75 (m, 3H), 7.60 (d, 2H), 7.45 (d, 1H), 7.40 (d, 1H), 7.20 (d, 2H), 7.15 (t, 1H), 6.90 (d, 2H), 6.65 (d, 1H), 5.70 (s, 2H), 3.85 (s, 3H), 1.20 (m, 2H), 0.95 (m, 2H).

Aufarbeitung

  1. temperatureThe solution was cooled in an ice bath
  2. washthe aqueous layer was washed 2 more times with DCM
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed
  6. customthe crude mixture purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-7b965da848074bbd87637f60839e13b8
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158671B2

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