Carbon Dioxide → 2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

HRID 1052270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1052270
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([CH2:11][CH2:12][C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[CH:14]=3)[N:9]=2)[N:4]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:3]=1[C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]2)=[CH:33][CH:32]=1.C([Li])CCC.[C:49](=[O:51])=[O:50]>O1CCCC1>[CH3:22][O:21][C:15]1[CH:14]=[C:13]([CH2:12][CH2:11][C:8]2[N:9]=[C:10]3[C:2]([C:49]([OH:51])=[O:50])=[C:3]([C:31]4[CH:36]=[CH:35][C:34]([N:37]5[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]5)=[CH:33][CH:32]=4)[N:4]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[C:5]3=[N:6][CH:7]=2)[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=1

Komponenten

5

Edukt 3

HCID 280Carbon Dioxide2×HCID 899624757-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[2,3-b]-pyrazineHCID 178418339Butyllithium

Produkt 1

HCID 899630612-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The a stirred solution of 7-bromo-2-[2-(3,5-dimethoxyphenyl)ethyl]-6-[4-(4-methylpiperazin-1-yl)phenyl]-5-{[2-(trimethylsilyl)ethoxy]methyl}-5H-pyrrolo[2,3-b]-pyrazine (55 mg, 82.7 μmol) in tetrahydrofuran (2 mL), n-butyllithium (2.5 M in hexanes, 50 μL, 0.125 mmol) was added at 78° C. After 10 minutes, dry CO2 (prepared by passing the CO2 through drying tube) was bubbled into the reaction. After 20 minutes, the reaction was quenched with saturated aqueous NH4Cl, then extracted with methylene chloride. The combined organic layers were dried over MgSO4, then concentrated to give the crude product (50 mg), which was used directly in the next step. LCMS calculated for C34H46BN5O5Si (M+H)+: m/z=632.3. Found: 632.3.

Aufarbeitung

  1. customthrough drying tube)
  2. customwas bubbled into the reaction
  3. waitAfter 20 minutes
  4. customthe reaction was quenched with saturated aqueous NH4Cl
  5. extractionextracted with methylene chloride
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c6f1b42825ae4396badc0e5a8aa4aaf8
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388185B2

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