Ammonia → HCID 70921718, Verbindung

HRID 2069134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069134
[CH3:1][C:2]1[C:15]([CH3:16])=[C:14]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1.CCN(C(C)C)C(C)C.[CH3:29][O:30][CH2:31][C:32](Cl)=[O:33].N>C1COCC1.CO>[CH3:1][C:2]1[C:15]([CH3:16])=[C:14]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:32](=[O:33])[CH2:31][O:30][CH3:29])[CH:6]=1

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 585648204-(2,3-Dimethyl-4-nitrophenoxy)pyridin-2-amine

Produkt 1

HCID 70921718HCID 70921718, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 4-(2,3-dimethyl-4-nitrophenoxy)pyridin-2-amine (110 mg, 0.424 mmol) in THF (3.0 mL) containing DIPEA (370 μL, 2.12 mmol) at 0° C. was added 2-methoxyacetyl chloride (155 μL, 1.70 mmol) in a single portion. The reaction mixture was warmed to RT for 1 hr and a solution of NH3 in MeOH (7M, 2.0 mL) was added and the resulting mixture maintained at RT for 16 hr and then evaporated in vacuo. The residue was partitioned between DCM (50 mL) and brine (40 mL) and the organic phase was seprated and dried (MgSO4) and was evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, 20-50% EtOAc in isohexane, gradient elution) to afford N-(4-(2,3-dimethyl-4-nitrophenoxy)pyridin-2-yl)-2-methoxyacetamide (94 mg, 67%) as an orange oil; Rt 2.14 min (Method 2); m/z 332 (M+H)+ (ES+).

Aufarbeitung

  1. temperaturethe resulting mixture maintained at RT for 16 hr
  2. customevaporated in vacuo
  3. customThe residue was partitioned between DCM (50 mL) and brine (40 mL)
  4. dry with materialdried (MgSO4)
  5. customwas evaporated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, 40 g, 20-50% EtOAc in isohexane, gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-aed2d25226024b81a063ca8fd3341b73
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299074B2

Notizen zur Reaktion

Wird geladen…