Diisopropylethylamine → N-(4-cyanophenyl)-N'-(1-ethyl-2,3-dimethyl-1H-indol-5-yl)-3-methylpentanediamide

HRID 2272557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272557
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([OH:16])=O)=[CH:5][CH:4]=1)#[N:2].[CH2:19]([N:21]1[C:29]2[C:24](=[CH:25][C:26]([NH2:30])=[CH:27][CH:28]=2)[C:23]([CH3:31])=[C:22]1[CH3:32])[CH3:20].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([NH:30][C:26]2[CH:25]=[C:24]3[C:29](=[CH:28][CH:27]=2)[N:21]([CH2:19][CH3:20])[C:22]([CH3:32])=[C:23]3[CH3:31])=[O:16])=[CH:7][CH:8]=1)#[N:2]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 3981627HCID 3981627, VerbindungHCID 64853091-ethyl-2,3-dimethyl-1H-indol-5-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 86729720N-(4-cyanophenyl)-N'-(1-ethyl-2,3-dimethyl-1H-indol-5-yl)-3-methylpentanediamideAusbeute 61,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the compound obtained in Step 1 (510 mg, 2.07 mmol), 1-ethyl-2,3-dimethyl-1H-indol-5-amine (390 mg, 2.07 mmol) and DIEA (1.085 mL, 6.21 mmol) in DMF (8 mL) was added HATU (1181 mg, 3.11 mmol), and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give the title compound (533 mg, 1.280 mmol, 61.8%) as a white powder.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3a4554a564bb447f845a6cfd4cc232be
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120776B2

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