1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67386157, Verbindung

HRID 1898543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1898543
[O:1]([C:8]1[N:9]=[C:10]2[C:16]([C:17](O)=[O:18])=[CH:15][N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:11]2=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)CCCN=C=NCC.[NH2:39][C@H:40]([CH:48]([CH3:50])[CH3:49])[C:41]([N:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1)=[O:42]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:49][CH:48]([CH3:50])[C@@H:40]([NH:39][C:17]([C:16]1[C:10]2[C:11](=[N:12][CH:13]=[C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:9]=2)[N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:26])([CH3:27])[CH3:25])[CH:15]=1)=[O:18])[C:41]([N:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1)=[O:42]

Komponenten

6

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 40459151HCID 40459151, VerbindungHCID 58522244HCID 58522244, Verbindung

Produkt 1

HCID 67386157HCID 67386157, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.10 g, 0.26 mmol), 4-dimethylaminopyridine (0.048 g, 0.39 mmol) and (3-dimethylamino-propyl)-ethyl-carbodiimide (0.075 g, 0.39 mmol) in CH2Cl2 (2 mL) was added (R)-2-amino-3-methyl-1-pyrrolidin-1-yl-butan-1-one (0.066 g, 0.39 mmol) in CH2Cl2 (0.5 mL). The reaction mixture was stirred at room temperature overnight, then quenched with water and extracted with ethyl acetate (3×). The organic layer was washed with water and saturated aqueous NaCl solution and dried over MgSO4, filtered and concentrated. The residue was purified by SiO2 column chromatography (0-100% EtOAc/hexanes) to afford 2-phenoxy-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-methyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide as a yellow oil.

Aufarbeitung

  1. customquenched with water
  2. extractionextracted with ethyl acetate (3×)
  3. washThe organic layer was washed with water and saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by SiO2 column chromatography (0-100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e8c2b9733817488b930aff2f4b6798ff
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518945B2

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