1,2-Dichloroethane → HCID 58522117, Verbindung

HRID 245806

Reaktionsgleichung

Reaktionsgleichung von HRID 245806
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:11]([OH:13])=O)=[CH:9][N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:5]2=[N:6][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH3:36][C:37]([CH3:42])([CH3:41])[C@@H:38]([NH2:40])[CH3:39].C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:39][C@H:38]([NH:40][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([Br:1])[N:3]=2)[N:8]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=1)=[O:13])[C:37]([CH3:42])([CH3:41])[CH3:36]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7004913(2S)-3,3-dimethylbutan-2-amineHCID 584385252-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Produkt 1

HCID 58522117HCID 58522117, VerbindungAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A round-bottomed flask was charged with 2-bromo-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (150 mg, 0.40 mmol), HOBT (68 mg, 0.44 mmol) and EDC (85 mg, 0.44 mmol). DMF (1.8 ml) was added followed by (S)-3,3-dimethylbutan-2-amine (0.10 ml, 0.73 mmol) and N,N-diisopropylethylamine (0.11 ml, 0.63 mmol). The reaction mixture was stirred at room temperature overnight then quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then combined, dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-20% EtOAc) to afford 97 mg (50%) of 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-1,2,2-trimethyl-propyl)-amide as a light brown oil.

Aufarbeitung

  1. customthen quenched with water
  2. extractionextracted with diethyl ether (2×)
  3. washThe combined organic layers were washed twice with water and once with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-20% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-53ef4725e97c4b0c8dc25900ecd350ff
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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