Triethylamine → HCID 59472366, Verbindung

HRID 2204812

Reaktionsgleichung

Reaktionsgleichung von HRID 2204812
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][NH2:8])=[O:6].[NH2:12][C:13]1[C:14]([C:30](O)=[O:31])=[N:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:29])[N:26]([CH3:28])[CH3:27])=[CH:21][CH:20]=2)=[CH:17][N:18]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CCOC(C)=O.O>[NH2:12][C:13]1[N:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([N:26]([CH3:27])[CH3:28])=[O:29])=[CH:23][CH:24]=2)=[N:15][C:14]=1[C:30]([NH:8][NH:7][C:5]([C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=1)=[O:6])=[O:31]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 3516403-FluorobenzohydrazideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 594717503-Amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazine-2-carboxylic acid

Produkt 1

HCID 59472366HCID 59472366, VerbindungAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-fluorobenzohydrazide (80.77 mg, 0.5240 mmol) was added to a solution of 3-amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazine-2-carboxylic acid (150 mg, 0.5240 mmol), triethylamine (53.02 mg, 73.03 μL, 0.5240 mmol) and TBTU (252.4 mg, 0.7860 mmol) in DMF (3.000 mL) and the resulting solution stirred at RT for 2 hours. The reaction was diluted with EtOAc and water and the layers separated. The aqueous layer was extracted further with EtOAc (2×) and the combined organics washed with water (3×), dried (MgSO4), filtered and concentrated to give the desired product as a yellow solid (172 mg, 78% Yield). MS (ES+) 423.13

Aufarbeitung

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted further with EtOAc (2×)
  3. washthe combined organics washed with water (3×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c1fdfff6fdbd4b93804719181c25598b
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365557B2

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