Acetonitrile → 2-Acetylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2080188
[NH2:1][C:2]1[N:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].[C:24](#N)[CH3:25].F[B-](F)(F)F.[O:32]=[N+]=O.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C.O>[C:24]([NH:1][C:2]1[N:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5])(=[O:32])[CH3:25]

Komponenten

8

Edukt 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 11073463Nitronium tetrafluoroborateHCID 231304232-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Produkt 1

HCID 231306832-Acetylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamideAusbeute 2,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 2-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-67 (50 mg, 0.15 mmol), acetonitrile (5 mL) and tetrahydrofuran (2 mL) was added nitronium tetrafluoroborate (0.50M sulfolane solution, 0.46 mL, 0.23 mmol) on an ice bath, and the solution was stirred overnight at room temperature. Water, ethyl acetate, tetrahydrofuran and an aqueous solution of saturated sodium bicarbonate were added to the reaction solution for extraction, washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:30), and the title compound (1.3 mg, 0.0035 mmol, 2.3%) was obtained as a white solid.

Aufarbeitung

  1. washwashed with brine
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:30)

Quellen und Nachweise

ORD-Eintrag
ord-b11ce95806314970b10bdb47a1e3c91f
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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