1,2-Dichloroethane → HCID 67386346, Verbindung

HRID 1898495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1898495
[CH:1]1([C:4]2[N:5]=[C:6]3[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.Cl.[NH2:25][C@H:26]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:27]([N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)=[O:28].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:1]1([C:4]2[N:5]=[C:6]3[C:12]([C:13]([NH:25][C@H:26]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:27](=[O:28])[N:29]4[CH2:30][CH2:31][CH2:32][CH2:33]4)=[O:15])=[CH:11][N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:22])[CH3:23])[C:7]3=[N:8][CH:9]=2)[CH2:2][CH2:3]1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57516598(R)-2-amino-3,3-dimethyl-1-(pyrrolidin-1-yl)butan-1-one hydrochlorideHCID 578296532-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Produkt 1

HCID 67386346HCID 67386346, VerbindungAusbeute 108,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 10 mL round-bottomed flask was charged with 2-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.12 g, 0.36 mmol), (R)-2-amino-3,3-dimethyl-1-(pyrrolidin-1-yl)butan-1-one hydrochloride (137 mg, 0.53 mmol), HOBt (61 mg, 0.40 mmol) and EDC (76 mg, 0.40 mmol). Then added DMF (1.6 mL) followed by N,N-diisopropylethylamine (0.16 mL, 0.92 mmol). The light yellow reaction mixture was stirred at room temperature overnight then quenched with water and extracted with diethyl ether (2×50 mL). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography over 8 g SiO2 with EtOAc/hexanes (gradient: 0-60% EtOAc) to afford 195 mg of (R)-2-cyclopropyl-N-(3,3-dimethyl-1-oxo-1-(pyrrolidin-1-yl)butan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide as a viscous yellow oil.

Aufarbeitung

  1. customthen quenched with water
  2. extractionextracted with diethyl ether (2×50 mL)
  3. washThe combined organic layers were washed twice with water and once with brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography over 8 g SiO2 with EtOAc/hexanes (gradient: 0-60% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-461c424353c1403198129b8102b14f49
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518945B2

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