Dimethylformamide → HCID 24764797, Verbindung

HRID 911794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911794
Cl.[Br:2][C:3]1[CH:4]=[C:5]([OH:16])[C:6]([NH:9][C:10]2[S:11][CH:12]=[C:13]([CH3:15])[N:14]=2)=[N:7][CH:8]=1.Br[CH:18]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[Br:2][C:3]1[CH:4]=[C:5]([O:16][CH:22]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21]2)[C:6]([NH:9][C:10]2[S:11][CH:12]=[C:13]([CH3:15])[N:14]=2)=[N:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 426142173-Bromo-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 86631475HCID 86631475, Verbindung

Produkt 1

HCID 24764797HCID 24764797, VerbindungAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-2-(4-methylthiazol-2-ylamino)pyridin-3-ol hydrochloride (1.0 g, 3.10 mmol), tert-butyl 3-bromopyrrolidine-1-carboxylate (WO 2003/062224) (1.01 g, 4.03 mmol), K2CO3 (1.29 g, 9.30 mmol), and DMF (20 mL) were reacted at 50° C. over the weekend. The reaction was cooled to room temperature, poured into water (250 mL) and extracted with EtOAc:ether (1:1). The organic layer was dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel (40% EtOAc in hexanes) to afford tert-butyl 3-(5-bromo-2-(4-methylthiazol-2-ylamino)pyridin-3-yloxy)pyrrolidine-1-carboxylate (584 mg, 41.4% yield) as a tan solid. 1H NMR (CDCl3) δ 8.42 (bs, 1H), 8.02 (s, 1h), 7.10 (d, 1H), 6.42 (s, 1H), 4.95 (m, 1H), 3.75-3.44 (m, 4H), 2.35 (d, 3H), 2.21 (m, 2H), 1.50 (s, 9H); Mass spectrum (apci) m/z=456.9 (M+H).

Aufarbeitung

  1. customwere reacted at 50° C. over the weekend
  2. extractionextracted with EtOAc:ether (1:1)
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (40% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-60ad39c6faf342398e588e3925eae6cb
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022223B2

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