Triphenylphosphine → 1-[4-(Aminocarbonyl)-6-chloro-2-pyridinyl]-4-piperidinyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate

HRID 2233955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2233955
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)[N:10]=1)[C:5]([NH2:7])=[O:6].[Br:18][C:19]1[CH:20]=[C:21]([C:25](O)=[O:26])[NH:22][C:23]=1[CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:18][C:19]1[CH:20]=[C:21]([C:25]([O:17][CH:14]2[CH2:15][CH2:16][N:11]([C:9]3[CH:8]=[C:4]([C:5]([NH2:7])=[O:6])[CH:3]=[C:2]([Cl:1])[N:10]=3)[CH2:12][CH2:13]2)=[O:26])[NH:22][C:23]=1[CH3:24]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 685182224-Bromo-5-methyl-1H-pyrrole-2-carboxylic acid2×HCID 860383812-Chloro-6-(4-hydroxypiperidin-1-yl)isonicotinamide2×

Produkt 1

HCID 866083101-[4-(Aminocarbonyl)-6-chloro-2-pyridinyl]-4-piperidinyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylateAusbeute 5,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-chloro-6-(4-hydroxypiperidin-1-yl)isonicotinamide (Intermediate 62; 123 mg, 0.48 mmol), 4-bromo-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 18) (98 mg, 0.48 mmol) and triphenylphosphine (138 mg, 0.53 mmol) were stirred in anhydrous THF and cooled to 0° C. DEAD (83 μl, 0.53 mmol) was added and the mixture was stirred at room temperature for 18 h. The mixture was filtered, diluted with EtOAc and washed with water and dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash chromatography eluting with EtOAc/hexane (4:1) to afford the title compound (11 mg).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. additiondiluted with EtOAc
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography
  7. washeluting with EtOAc/hexane (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-ea6c5af72e6d4271ba187d29b02a0df9
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709503B2

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