Triethylamine → 3-amino-6-bromo-N'-(3-methylthiophene-2-carbonyl)pyrazine-2-carbohydrazide

HRID 78628

Reaktionsgleichung

Reaktionsgleichung von HRID 78628
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[CH3:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18]([NH:20][NH2:21])=[O:19].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CCOC(C)=O.O>[NH2:1][C:2]1[C:3]([C:9]([NH:21][NH:20][C:18]([C:14]2[S:15][CH:16]=[CH:17][C:13]=2[CH3:12])=[O:19])=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27600843-Methylthiophene-2-carbohydrazideHCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Produkt 1

HCID 594723013-amino-6-bromo-N'-(3-methylthiophene-2-carbonyl)pyrazine-2-carbohydrazideAusbeute 36,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 3-amino-6-bromo-pyrazine-2-carboxylic acid (13.26 g, 60.82 mmol) and 3-methylthiophene-2-carbohydrazide (10 g, 60.82 mmol) in DMF (95.00 mL) cooled in an ice bath was added Et3N (7.385 g, 10.17 mL, 72.98 mmol) followed by TBTU (23.43 g, 72.98 mmol) portionwise after complete addition, the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with EtOAc (50 mL) and water (50 mL). The layers were separated and the organic extracts washed with water (1×50 mL) and brine (1×50 mL), dried over MgSO4 and concentrated to leave a brown solid (7.85 g, 36% yield) which was used directly in the next step without further purification.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. additionportionwise after complete addition
  3. customThe layers were separated
  4. washthe organic extracts washed with water (1×50 mL) and brine (1×50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-55330aedf68643dbaa35d72ee088f145
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841308B2

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